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Fall in Massachusetts: 12 Must-Visit Destinations & Fall Fun Ideas (2023)

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Looking for where to go to check out Massachusetts ‘ fall foliage? Look no further!

This list of 12 must-visit spots for fall in Massachusetts will lead you to the best leaf peeping and fall fun in the Bay State. In addition to stunning scenery, this New England state offers a wide world of fall fun for both residents and visitors alike.

With plenty of hiking options , scenic drives , wholesome family fall fun activities , and a town that is sure to get you in the Halloween spirit, fall in Massachusetts is where it’s at!

Table of Contents

When to Visit Massachusetts for Fall Colors

Massachusetts typically sees peak fall foliage in the first couple of weeks of October, but check out the Weather Channel’s fall foliage map for real-time tracking.

I was recently in Massachusetts for the first week of November, and there were still vibrant pops of color to be found throughout the state, including the Berkshires and Plymouth MA.

The Bay State has plenty to do and see all year round, but come fall the landscape becomes an even more spectacular setting for your adventures in Massachusetts.

Fall in Massachusetts: Where to Go

Monument mountain.

Fall foliage in Massachusetts stretches out under a setting sun

Located in Great Barrington, a town in the Berkshires that Vogue once described as “quietly cool,” Monument Mountain offers scenic views from its 1,624-foot summit that allow you to look out across the Housatonic River Valley, with the Catskills of New York in the distance.

Monument Mountain has a storied place in literary history as well, as it is said that literary greats Herman Melville and Nathaniel Hawthorne climbed the summit together before having to shelter in a cave due to rough weather, during which the inspiration for Moby Dick was born.

Lower Berkshires Waterfalls

Bash Bish Falls in Massachusetts is surrounded by fall foliage

There are plenty of waterfalls with gorgeous fall foliage backdrops to choose from in the Bay State, but Campbell Falls , Race Brook Falls , and Bash Bish Falls are all within easy driving distance of one another in the picturesque towns of New Marlborough, Sheffield, and Mount Washington, respectively, and are well worth adding to the list of the best places to visit in Massachusetts in the fall!

With multiple falls that vary in length between 50 and 100 feet, the hikes out to these waterfalls are all considered moderate but it is said that if you approach Bash Bish Falls from the Massachusetts side, it is a much steeper and more advanced hike than approaching from the New York side.

Bash Bish Falls is the highest single-drop waterfall in the entire state and a regional favorite.

Pleasant Valley Sanctuary

Fall trees in the Berkshire Mountains

Situated in the adorable town of Lenox, Pleasant Valley Sanctuary is comprised of over a 1,000-feet of protected land and wildlife sanctuary nestled at the base of Lenox Mountain. There are multiple hiking trails to choose from as you make your way through the blazing orange, ruddy crimson, and burnished gold of the autumn leaves.

Lenox is also home to some pretty cool places to visit, like Tanglewood , the iconic music venue that serves as a summer performance space for the Boston Symphony Orchestra, and The Mount , the breathtaking estate of early 20 th -century author Edith Wharton.

The Mohawk Trail

A hairpin turn on a fall foliage road in the Berkshires

The Mohawk Trail is a historic route (with alternative routes , too!) that leads through the scenic northern Berkshires, which are absolutely bursting with fall color during prime leaf peeping season. 

It winds through picturesque New England towns that offer lots of lovely side trip ideas, like the Bridge of Flowers in Shelburne Falls, an old trolley bridge that was reimagined as a walkthrough flower garden, and for the more adventurous,  Zoar Outdoor Ziplining in Charlemont lets you take in the MA fall foliage from an entirely different vantage point as you soar through the canopy of trees. 

MA’s Mohawk Trail is one of the oldest scenic routes in the country and is a beautiful drive all year round, but if you can do it while the trees transform into a vivid palette of gold and burnt orange with dashes of crimson, you should. Don’t worry, there are scenic overlook spots along this route to hop out and take advantage of the plethora of photo opportunities!

Mount Sugarloaf State Reservation

A river in Massachusetts is lined with fall foliage at sunset

You can drive or hike up to the lookout tower of Mount Sugarloaf State Reservation , but the visual reward will be the same either way: Sweeping views of the Connecticut River and Pioneer Valley below and the Berkshires in the distance.

Looking across the valley, you see the quintessential New England aesthetic with farmland, river, and you might even catch a glimpse of a beautiful white steeple in the village below. As the leaves turn color, the views here go from lovely to absolutely stunning!

Quick heads up: the road to drive up is reported to be fairly narrow, so if you’re driving an extra-wide vehicle, it’s probably best to park and hike up.

Maudslay State Park

A woman smiles as she enjoys fall foliage in Massachusetts at a park

Positioned on the Merrimack River in the cute coastal community of Newburyport, Maudslay State Park is a historic fixture in Newburyport as a former private estate that has since been adopted by the state, providing visitors with access to miles of easy to travel trails, old stone bres, and even a 19 th -century garden!

As the season shifts from summer to autumn, the blazing fall foliage is reflected in the Merrimack River, with an easy to follow trail that meanders alongside. The town of Newburyport is also less than an hour from other must-visit locations like Salem , Rockpor t, and Marblehead , so be sure to take advantage of its location to check out these other coastal gems!

Mount Greylock State Reservation

A tall memorial tower sits at the top of Mount Greylock in Massachusetts

Located in the picturesque town of Adams, the summit of Mount Greylock is 3,491 feet and the highest point in Massachusetts. You can drive or hike to the top, and on a clear day you can see up to 90 miles away, catching parts of 4 states and 5 mountain ranges, and the fall foliage views go on and on and on.

Atop Mount Greylock is an impressive 92-foot tall granite Veterans War Memorial lookout tower and Bascom Lodge , providing meals and lodging for travelers looking to stay overnight on the mount. Be aware that the temperature drops significantly as you near the summit, so be sure to dress accordingly!

Road access to Mount Greylock is closed on November 1, so don’t wait too long to catch the incredible autumn views atop the summit of this gorgeous natural wonder.

The Salem Witch House is seen with pumpkins in front for fall

The perfect Massachusetts town to visit in October, Salem is full of fun things to see and do to kick off your fall fun! Not only will you find ghost tours , haunted places , great restaurants , and cool places to stay , but the fall colors in Salem MA aren’t half bad, either.

In fact, Salem is full of fun FREE things to do , too, including taking yourself on a little tour of all the sites where Hocus Pocus was filmed.

Fall in Massachusetts: What to Do

Go apple picking.

Someone is reaching up to pick apples off a tree

There are several great pick your own apple orchards across the Bay State , and is there anything more quaint and wholesome than heading out on an early fall day to pick your own apples?

Visit a Cranberry Bog

Crimson red cranberries float on the top of cranberry bogs in Massachusetts

One of Massachusetts’ claims to fame is their cranberry bogs, and fall is harvest time!

Harvesting cranberries is an interesting process where the cranberry fields are flooded so the fruit can float to the top, making it easier for the machinery to harvest them. Some cranberry bogs will even let you strap on a pair of chest waders and hop in the bog to help, like Benson’s Pond in Middleboro!

Play at a Pumpkin Patch

Two little girls carrying a pumpkin through a pumpkin patch

Of course, pumpkin patches are just good, old-fashioned fall fun! There are several great pumpkin patches in Massachusetts that offer great family activities like hay rides and petting zoos, so if you’re looking for fun family things to do in MA, consider heading to the nearest pumpkin patch.

Get Lost in a Corn Maze

Empty path through a corn maze

Just about the only time “getting lost” is fun, corn mazes are another one of those simple fall activities that deliver big on fun, and there are plenty of them in Massachusetts to choose from.

Sometimes you’ll even stumble across a corn maze offering quintessential fall in MA staples like cider donuts… yum!

Even if you miss peak foliage – like I did – you should still add a visit to Massachusetts in the fall to your leaf peeper’s bucket list!

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  • 16 Enchanting New England Fall Foliage Destinations
  • 10 Abandoned Places in Massachusetts
  • Fall in New England: The Best Towns, Orchards, Farms, Foliage, & Festivals

Pinterest graphic reading

Western Mass.

Western Mass.

Cape Cod & The Islands

Cape Cod & The Islands

Central Mass.

Central Mass.

Boston

North of Boston

South of Boston

South of Boston

Fall foliage in massachusetts 2024, waves of color from the berkshires to the ocean.

Massachusetts's Central and Berkshire Mountains regions have lofty peaks and gorgeous river valleys that are ideal for seeing the leaves change color during fall foliage season. Great views of fall color – starring the sugar maple -- also are found in the North of Boston Cape Ann region , and around Plymouth, MA , where cranberry bog harvests brighten the landscape. Choose a scenic foliage drive below. Watch for farm stands and pick-your-own farms!

Essential Information :

  • Annual Foliage Map (Weather.com)
  • The Berkshires Blog : A great resource for foliage viewing each fall
  • Pick Your Own Farms : Stop for fresh apples, veggies, cider, or pumpkins
  • Massachusetts State Map
  • Great Things to Do in Massachusetts

Truro Sea Breeze -  Lighthouse in Fall on Cape Cod, MA - Photo Credit Thomas Schoeller Photography

© Thomas Schoeller Photography

Foliage driving routes in massachusetts :, the berkshires and western mass., mohawk trail west – greenfield to north adams (37 mi.).

massachusetts towns to visit in fall

Points of Interest :

  • In Greenfield, MA , take a pleasant walk and wear out your kids at Rocky Mountain Park on the Connecticut River. This forested ridge stretches along the river and has hiking and biking trails and the popular Poet’s Seat Tower . Nice for walking, bird-watching, and peaceful contemplation.
  • Shelburne Falls, MA , a bit west of Greenfield on Route 2, is a pretty town on the Shelburne River. Right in its center is the famous Bridge of Flowers , a former trolley bridge that is planted with 500 varieties of flowers, vines, and shrubs (open April 1 to October 30). Stroll to the Salmon Falls Gallery , then watch the river racing over a mesmerizing series of falls.
  • Continue through Mohawk State Forest . Before you get to the next major town, North Adams, MA , you will navigate a crazy , nearly 360-degree hairpin turn.
  • With advance planning, you can schedule a zip line tour at Zoar Outdoor or Berkshire East , both in Charlemont, MA , very close to Route 2.
  • North Adams, MA is full of culture and shopping and interesting sights. Consider stopping into MassMoCA (the Massachusetts Museum of Contemporary Art). MASS MoCA exhibits work by many of the most important artists of today; it hosts dozens of performances year-round.
  • At the Natural Bridge State Park in North Adams, MA , you will be stunning by nature’s artistic beauty when you see a naturally formed white marble arch and man-made white marble dam.

Side Trips: Before leaving or after arriving in North Adams, MA , swing southward for a drive to the stunning summit of Mount Greylock .

Fall View at Mohawk Trail State Forest - Photo Credit Joshua Bellows via Google Maps

Summit of Mount Greylock (27 miles)

massachusetts towns to visit in fall

Connecticut River Scenic Byway in the Pioneer Valley (50 mi.)

Points of interest: :.

  • Springfield, MA is home to the famous Springfield Museums, including The Amazing World of Dr. Seuss Museum , honoring the hometown hero of kids everywhere, Theodor Geisel, or Dr. Seuss. You are guaranteed to love it. .
  • On the flip side of the age spectrum in entertainment, in Springfield, MA travelers will find The MGM Grand Casino , opened here in 2018 by MGM Resorts International. It covers three blocks in the center of Springfield and presents a huge array of slots, table games, dining, and fun.
  • South Hadley, MA is home to Brunelle's Marina on the Connecticut River. You might suspend your road trip for a short river cruise on the Lady Bea , docked at Brunelle’s. The 75-minute cruise meanders up the Connecticut River to Northampton. Cruises run from Memorial Day to Columbus Day.
  • Mount Holyoke College Botanic Garden encompasses the Mount Holyoke College campus in South Hadley, MA , including an arboretum and numerous gardens, as well as the Talcott Greenhouse. Open daily, sunrise to sunset.
  • You can spend a day in old New England at Historic Deerfield, MA . The 330-year-old village center has 12 houses dating to the 1700s and 1800s, along with fascinating and always-changing exhibits and workshops at the Flynt Center of Early New England Life . Reserve your appetite for a fine meal in the nearby Champney’s Restaurant and Tavern .
  • The Quabbin Reservoir , directly east of the town of Amherst, MA , is a beautiful passive recreation area, offering year-round opportunities for walking, biking, fishing and snowmobiling.
  • Moving along routes 63 and 47, you are traveling through the bread basket of Massachusetts. Many farms that date back more than 100 years. You can indulge your sweet tooth when you reach the Northfield Creamie in Northfield, MA , the northern terminus of this drive.

This drive threads between Northampton and Amherst, MA , where several great eating places reside. Get your falafel fix and more at Pita Pockets . The Northampton Nourish Juice Bar opened the full-service Nourish Wellness Café , serving juices and smoothies and a signature Wellness Bowls. Foreign food choices in Amherst, MA also now include Lebanese cuisine at Malek Shawarma and food of Nepal, India, and Bhutan at Himalayan Friends Corner.

Mystique Fall Barn in the Southern Berkshires - Photo Credit Thomas Scholler Photography

Johnny Appleseed Country - North Central Mass.

Hiking in North Central Mass. - Photo Credit Visit North Central MA

  • Route 2 threads straight through the North Central region, with a variety of off-ramps to various places of interest. One place to start your exploration is the Johnny Appleseed Visitors Center in Lancaster, MA . Along with maps and info, you can get a look at the Big Apple of New England sculpture and three trees on the property that are direct descendants of a tree planted by Johnny Appleseed (1774-1845). From the Visitor’s Center, various choices await in every direction, branching off Route 2 (see map link above).
  • Fitchburg Art Museum in Fitchburg, MA exhibits a surprisingly diverse collection of art for every curious visitor, with permanent and changing exhibits.
  • Also in Fitchburg, MA is the RB Racing Museum honoring the memory of local NASCAR © legend Ron Bouchard. Open to the public by appointment.
  • Moving south towards Clinton, MA , visit the unique and reverential Museum of Russian Icons for a vastly different experience from auto racing adventure.
  • In Boylston, MA , enjoy the beautiful and varied landscapes at The New England Botanic Garden at Tower Hill . The garden hosts lots of seasonal celebrations, including at Christmastime.
  • Recreation areas? Got ’em, and they are lovely and alluring in all seasons. Wachusett Mountain State Reservation in Princeton, MA is home to a ski area, and also a fine place to view the colors of fall foliage.
  • Lake Dennison State Recreation Area in Winchendon, MA is a beautiful place for hiking and outdoor sports, as is Leominster State Forest in Westminster, MA .
  • For a wonderful immersion in nature, art, and Massachusetts history, visit Fruitlands Museum in Harvard, MA , a utopian community co-founded in 1843 by Amos Bronson Alcott, father of the famous author.

North of Boston: Merrimack Valley & Cape Ann

Greater merrimack valley tour.

Fall on the Farm in Lincoln, MA - Photo Credit Greater Merrimack CVB

  • Minute Man National Historic Park in Concord, MA comes alive with a re-enactment of the “shot heard ‘round the world” every April. But the park is open and fun to visit at any time of the year, telling the stories of America’s revolt from British rule. It is a great place to visit with kids, with lots of outdoor and indoor places to see and stunning in the fall. Don’t miss seeing the North Bridge.
  • Lexington Battle Green in Lexington, MA is one epicenter of the American Revolution. Also, a classic New England town green that charms visitors from around the world.
  • Concord, MA ’s Orchard House - See the historic 1690 house and the place where Louisa May Alcott wrote the beloved classic Little Women .
  • Walden Pond State Reservation in Concord, MA is a large and beautiful state park that pays homage to its most famous short-term resident, Henry David Thoreau , author of Walden . A universal trail leads to a replica of Thoreau's single-room cabin.
  • The deCordova Sculpture Park and Museum in Lincoln, MA is great outdoor and indoor space displaying marvelous sculptures in permanent and rotating exhibits. Lots of seasonal events at this very welcoming place.
  • Concord’s Colonial Inn in Concord, MA is a very pleasant stop for lunch or dinner on a scenic fall foliage drive – or any time of the year. It offers dining on the porch and two restaurants, Liberty, a gastropub, and Merchant’s Row, offering a lavish Sunday brunch.
  • The Lowell National Historical Park describes the history of America’s Industrial Revolution in the very textile mills, and on the canals where it happened.
  • Mill No. 5 in Lowell, MA is an indoor reproduction of a historic streetscape from the times when this city roaring with industrial productivity. Here, visitors find lots of owner-operated shops, a farm-to-table cafe, a live music performance space, and a yoga studio.

Lexington to Lincoln to Concord

This drive, starting in the town of Lexington, MA , is only six miles, but it takes you through beautiful scenery and also the flash points of the early years of the American Revolution. History buffs may want to park in Lexington and take a narrated bus tour with Liberty Ride . The tour passes sites like the Lexington Battle Green, North Bridge, Battle Road, Orchard House, Colonial Inn, the Old Manse, Concord Museum , and Emerson House .

Fall Foliage in Massachusetts - Cyclists on the Minuteman Bikeway in Lincoln/Lexington/Concord MA - Photo Credit MOTT

Find more Scenic Drive Tours in Massachusetts .

Cape Ann Tour - Rockport, Gloucester, Essex & Newburyport, MA

Rockport, Gloucester, Essex & Newburyport - Massachusetts Foliage Drives

  • Newburyport, MA is a fun town for dining, shopping, browsing art galleries, and strolling. A brick plaza – in contrast to the traditional New England green – is the heart of the town, and lots of public events happen here. If you visit in the fall, you might easily stumble upon an Oktoberfest or a family fall festival.
  • Salisbury Beach State Reservation in Salisbury, MA is a long, beautiful beach, anchoring at the north end by a slightly honky-tonk-ish commercial area where you can get ice cream and classic summer foods like fried dough, and let kids bliss out for a little while at the arcade.
  • Plum Island is an 11-mile long barrier island a short drive from Newburyport, MA . On your way out to the island, you will pass the Audubon Society's Joppa Flats Educational Center . Stop in for information about the seaside life you will encounter as you stroll the barrier beach. Inquire about bird watching tours, for today or another visit.
  • Castle Hill on the Crane Estate in Ipswich, MA . This historic home is a joy to visit. Start, if you wish, with a tour of the Stuart-style mansion (offered seasonally) and then enjoy the gardens, the spectacular Grand Allee – a wide, terraced, grassy path from the mansion to the beach, framed by marvelous statues – and the views from the whole property of the seashore and a giant estuary and marsh meadow below.
  • Essex Shipbuilding Museum in Essex, MA is a wonderful way to become immersed in the ancient ship-building culture of Massachusetts. Small museum with neat tools, boat parts, sea charts. Kids love it!
  • Gloucester, MA is a historic fishing port, made famous by the movie The Perfect Storm . Take a look at the Gloucester Fishermen's Memorial on Western Avenue. The Annisquam Lighthouse on Wigwam Point River is a beauty. Dogtown is an unusual walking park north of town, off Route 27. It is a wild area filled with mysterious mottos carved into boulders, mementos of a vanished community.
  • Rockport, MA is famous for its many great galleries. Walk out onto Bearskin Neck for souvenir shopping and look at Motif No. 1 , the often-photographed fishing shack, and Straitsmouth Island Lighthouse . Dock Square and Main Street are chock full of shopping and artwork.

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A walk through the fall landscape in the Berkshires, Massachusetts.

10 Top Places To Visit In Massachusetts In The Fall

Massachusetts is a fantastic place to visit in the fall, as there are plenty of things to see and do during this season. When it comes to leaf peeping, the state offers some of the top spots to get the best views, and that's not all. Fall is a great time to explore the interesting history of Massachusetts without dealing with the summer crowds. With places like Salem in the state, those who want some spooky adventures will also be satisfied. So, here are some of the best places in the state waiting to welcome you this fall.

New Bedford

The ciyscape of New Bedford, Massachusetts.

Fall in New Bedford is a relaxing experience as the beaches are uncrowded, the gardens are gorgeous, and the weather is excellent during this period. Enjoy an exciting fall vacation here by visiting the Candy Apple Farm to taste some delicious apple treats and coffee, and then head over to the Dartmouth Orchards to pick some apples. Next, check out the New Bedford Whaling Museum to see interesting whale exhibits on display. For more adventures, get on a whale-watching tour, as these majestic creatures can still be seen in the waters around the town in the fall. For those around in mid-October, New Bedford has its own Oktoberfest, featuring an abundance of craft beer and live entertainment. 

People visiting the annual Haunted Happenings event in Salem, Massachusetts,

Salem  is an ideal spot for an unforgettable fall vacation. In addition to the beautiful fall foliage that can be witnessed across its streets, Salem also offers one of the most exciting Halloween experiences one can have anywhere in the world. Thanks to its history full of chilling events, plenty of haunted places spread out across the city will scare the bravest ghost hunters. For an exciting experience, visitors can take a self-guided tour of all the locations used in the filming of Hocus Pocus and also check out some haunted places such as - the Hawthorne Hotel, the Salem jail, and the Turner house. Do not miss out on the Proctor's Ledge, which is believed to be the exact location where the alleged Salem witches wehre hanged. 

Lower Berkshires Waterfalls

Bash Bish Falls in Berkshires, Massachusetts.

There are many waterfalls in Massachusetts with breathtaking views of the changing leaves. However, Race Brook Falls in Sheffield, Campbell Falls in New Marlborough, and Bash Bish Falls in Mount Washington are the most gorgeous worth visiting in the fall. These waterfalls are near each other, and the trails to access them are incredibly beautiful and rated as moderate, making them safe and convenient for all hiking levels. Bash Bish Falls is particularly stunning and worth visiting year-round as it is the highest single-drop waterfall in the state, with a height of 60 feet (18 m). 

The beautiful town of Cape Cod in Massachusetts.

Cape Cod is the easternmost peninsula  of Massachusetts, famous for its unusual shape, which looks like an arm flexing its muscles. Besides its unique formation, this peninsula has grown to be among Massachusetts's most well-liked vacation destinations. In addition to the changing scenery that can be witnessed here in fall, the peninsula is home to many attractions like the Cape Cod National Seashore, which houses lighthouses, swimming beaches, cranberry bogs, and trails for hiking and biking. Regarding history, Cape Cod is home to the resort town of Provincetown, which is famous for being the initial landing place of the Pilgrims in the US. Cape Cod also has several other towns and villages that promise incredible adventures and scenery, and visiting them in fall is a great way to escape the crowds and take advantage of low prices and the great weather. 

The Mohawk Trail

The beautiful flower bridge in Shelburne Falls, Masachusetts.

The Mohawk Trail is an iconic path in the Northern Berkshires, and it is a must-see during the peak fall season. The road stretches for over 60 miles and winds through charming towns and villages surrounded by forest-covered mountains and valleys. Part of the trail also runs alongside the picturesque Deerfield River, adding to its beauty. During fall, riding on this road feels magical, and in addition to the scenery, there are plenty of side trips that will make the experience even more unforgettable. For some ideas, check out the Bridge of Flowers in Shelburne Falls, which is an old trolley bridge transformed into a walkthrough flower garden. For the more daring, visit the Zoar Outdoor Ziplining found in Charlemont, where one can see the fall foliage from a whole new perspective while soaring above the trees. 

Mount Sugarloaf State Reservation

View of the Connecticut River from Mount Sugarloaf.

Mount Sugarloaf State Reservation is a gorgeous area in South Deerfield that offers expansive views of the Connecticut River Valley, the Pioneer Valley, and the Berkshire Mountains. While the views are beautiful year-round, fall is, without doubt, the most beautiful time to be here. During this season, guests hiking on one of the trails will be spoiled with views of the Connecticut River surrounded by typical New England farms and an abundance of trees flaunting all kinds of fall colors. Besides hiking, visitors to Mount Sugarloaf State Reservation can engage in mountain biking and picnicking, as they also offer great views.  

Boston, Massachusetts, in fall.

Boston is among the oldest cities in the country  and a great place for an unforgettable fall vacation in Massachusetts. This city is particularly famous for its history, which can be seen in its numerous historic attractions, one of which is the Freedom Trail. This trail is a 2.5-mile walk that goes through some of the most important colonial and revolutionary sites in American history. Some of these sites include the Paul Revere House, which is the oldest house in Boston, and the USS Constitution, which is the oldest commissioned US Navy Ship. 

Besides its historical appeal, Boston also has amazing natural scenery, exciting ghost tours, and outdoor activities that will make a fall vacation memorable. To witness the best fall scenery in the city, take a stroll around the Boston Public Garden or head over to Franklin Park to combine wildlife watching and leaf peeping. 

Pleasant Valley Sanctuary

The town of Lenox, Massachusetts.

Pleasant Valley Sanctuary is a wildlife sanctuary positioned at the foot of Lenox Mountain in the quaint town of Lenox. The wildlife sanctuary covers an area of about 1,405 acres, and it is home to miles of trails, a large pond, camping sites, and incredible wildlife. However, the most amazing feature this sanctuary offers in fall is the diverse colors that can be witnessed in its lush forest areas. Red, yellow, orange, green, and gold colors are all displayed in the sanctuary during this season, creating amazing photo opportunities. Visitors can pick from various hiking trails to get up close to the rich fauna and flora in this sanctuary. For more things to do around, head over to the town of Lenox to see some of its attractions like - The Mount, which is the magnificent mansion of early 20th-century author Edith Wharton. Also, check out Tanglewood, the legendary music theater that hosts summer concerts for the Boston Symphony Orchestra.

Maudslay State Park

The Maudslay State Park in Massachusetts.

Maudslay State Park is a historic landmark in Newburyport that was once a private estate later adopted by the state. The park is situated on the Merrimack River and is characterized by well-designed gardens, rolling meadows, charming lakes, white pine, and historic stone bridges. The park is also a nesting site for bald eagles. All these make the park a paradise for exciting outdoor activities and nature photography, especially in the fall. There are miles of easily navigable trails in this park, which allows visitors to fully explore its amazing scenery and history. Other activities like biking, horseback riding, and picnicking can be done here as well.

Mount Greylock State Reservation

Spectacular fall colors at the Mount Greylock State Reservation, Massachusetts.

Mount Greylock State Reservation is a 12,000-acre area that protects Mount Greylock - Massachusetts' highest point, a height of 3,491 feet. The mountain is the main attraction here, and on a clear day, it offers uninterrupted views of parts of four states and five mountain ranges from more than 70 miles away. In fall, the views are simply breathtaking, making it one of the best times to visit. Also on a part of the mountain is the striking 92-foot-tall granite Veterans War Memorial observation tower and the Bascom Lodge, which serves food and accommodations to visitors who wish to spend the night on the summit. 

Fall is an amazing time in Massachusetts. It is arguably the best time to visit this state for a more laid-back experience combined with scenery. While the list of vacation destinations in Massachusetts is endless, these places are the best for those seeking an unforgettable fall vacation. This is because they all come with gorgeous fall foliage, interesting history, and opportunities for outdoor adventures. Some like Pleasant Valley Sanctuary even offer opportunities to see wildlife roaming in the foliage, creating views that can only be described as magical. 

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Massachusetts Fall Foliage Guide

From the best time for peak color to the perfect foliage towns and road trips, our Massachusetts fall foliage guide will help you plan a great Bay State escape this autumn.

By Yankee Editors

Oct 04 2021

shelburne-falls-ma

Foliage in Shelburne Falls, Massachusetts

Planning a trip to Massachusetts this year for some autumn color and fun? Our Massachusetts fall foliage guide is here to help. Learn the best time to see the leaves change, discover our favorite foliage towns and scenic routes, and read up on a few fantastic fall attractions.

Massachusetts Fall Foliage | Best Time to Visit

While the timing is slightly different every year, Massachusetts sees its best fall color, moving from north to south, starting in mid-to-late September and extending through mid-October.

Some of our favorite regions in Massachusetts for enjoying fall color are the Upper Pioneer Valley during middle peak (end of September to mid-October) and Cape Ann , including the popular tourist town of Rockport, during late peak (mid-October to early November). That said, you’ll find fantastic pockets of color in every corner of the state throughout the season.

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Learn more about finding peak color in New England in the 2018  Yankee  feature  “Peak Perfection.”

Best Massachusetts Fall Foliage Towns

.css-95i9ee{display:block;position:relative;padding-bottom:68.28571428571428%;}.css-95i9ee noscript>img,.css-95i9ee img{position:absolute;height:100%;} 1. williamstown.

Located in the shadow of Massachusetts’s highest mountain — Mount Greylock, in nearby Adams — Williamstown may be the ultimate college town: Its mix of eclectic architecture and inviting green spaces can’t help but inspire lofty thoughts. While the drive up Mount Greylock affords dizzying views of the Berkshires and the Taconic Range, a favorite hike for Williams College students is the two-mile pitch up to Pine Cobble, a quartzite outcropping with a panoramic view of the so-called Purple Valley and church spires below.

Local poet Emily Dickinson knew how to appreciate the subtle beauty of nature, from a certain slant of light to the changing shades of a sugar maple. Now her family homestead is one of the many cultural attractions that come alive each fall when the students return to picturesque Amherst College. The highlight of the season is the annual Fall Foliage Walk, which goes from the town common, across the campus, to the tree-lined ridge of the Norwottuck Rail Trail.

3. Shelburne Falls

Take an abandoned trolley bridge, plant it with blooming greenery, and voilà! You have an instant town icon and tourist attraction. But the Bridge of Flowers is just the beginning of the appeal of this stranded-in-time turnoff from the Mohawk Trail, now a haven for artisans, who sell their wares in studios near the falls on the Deerfield River.

Western Massachusetts Foliage Drive | Directions and Things to Do

Best Massachusetts Fall Foliage Drives

The mohawk trail.

The loveliest way to reach the Berkshires from the east is to drive the Mohawk Trail slowly, with the windows open, stopping for photos and drinking in the mountain views. Part of Route 2, from Orange to Williamstown, the Mohawk Trail is 65 miles or so of curves, climbs, drops, and one hold-your-breath hairpin turn above the Hoosic Valley that’s an attraction in its own right.

The Connecticut River Ride

Following the Connecticut River through Western Massachusetts, this New England road trip feels like taking a journey back in time. Start in South Hadley, drive through Skinner State Park to the summit of Mount Holyoke for river views, browse for books and grab lunch at the  Montague Bookmill , and get in a final scenic stroll in Turners Falls before winding up at the New Hampshire border.

Learn more about the Connecticut River Ride in the 2014 Yankee feature “Slow Foliage Drives Through Fall Color” and get even more New England foliage road trip ideas in our list of 14 Favorite Fall Drives in New England . 

Best Massachusetts Fall Activities

Hike (or drive) mount greylock.

At 3,491 feet, Mount Greylock is the highest point in Massachusetts and has views that encompass five states. Located on a state reservation that borders several nearby towns, including Williamstown, Mount Greylock is heaven for hikers, but it also has an auto road with a parking lot at the summit.

Pick-Your-Own Apples

Nothing says autumn like biting into a crisp apple, especially one you’ve just picked yourself. Massachusetts offers a number of excellent apple orchards, including Red Apple Farm in Phillipston and Clarkdale Fruit Farms in Deerfield. Russell Orchards in Ipswich is another popular choice for apple picking and warm apple cider doughnuts.

Looking for more fall fun? Discover our picks for the  best pumpkin festivals in New England  and the  best corn mazes in New England .

What Massachusetts fall foliage picks would you add to the list? Let us know!

This post was first published in 2020 and has been updated. 

More Foliage Guides: Maine Fall Foliage Guide New Hampshire Fall Foliage Guide Vermont Fall Foliage Guide

More new england fall foliage: guide to new england fall foliage train tours 10 places to visit in new england in fall favorite new england fall foliage tours.

massachusetts towns to visit in fall

Yankee Editors

Fall Is Coming And These Are The 10 Best Places To See The Changing Leaves In Massachusetts

massachusetts towns to visit in fall

Massachusetts native. Freelance writer and strawberry eater.

More by this Author

There’s nothing like fall in New England, and the autumn season in Massachusetts is especially glorious. When you want to see the best of the changing leaves in the Bay State, head to one of these spectacular spots. These are some of the best places to visit in Massachusetts in the fall , and you don’t want to miss the spectacular display of color Mother Nature puts on!

massachusetts towns to visit in fall

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massachusetts towns to visit in fall

Where is your favorite place to go to see the best foliage in Massachusetts? Do you have any secret leaf-peeping spots? Share and let us know in the comments. If you’re looking to take a fall road trip, check out these Massachusetts country roads that are pure bliss in the fall .

OnlyInYourState may earn compensation through affiliate links in this article. As an Amazon Associate, we earn from qualifying purchases.

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Which hiking trails in Massachusetts are best in the fall?

One of the best ways to see the fall colors in Massachusetts is by getting out of your car, lacing up your boots, and tackling the trails. Wachusett Mountain State Reservation features more than 17 miles of beautiful hiking trails which just transform during the fall. On the other side of the state, the Monument Mountain Trail in Great Barrington offers sweeping views of the Housatonic River Valley and the Berkshires, and this 3-mile loop might just be one of the best hiking trails in Massachusetts in the fall .

When can I see peak fall foliage in Massachusetts?

Timing is everything when you’re on the hunt to see the fall colors in Massachusetts. The season typically starts towards the end of September, and peaks around the first or second week of October. Of course, Mother Nature is going to do what she pleases, so we are often left to just sit around and wait patiently! You can always take a road trip in Massachusetts starting in the northwestern part of the state and then make your way east since the western part of the state typically sees the colors begin to change first.

Where can I go apple picking in Massachusetts?

Apple picking is a popular fall activity in Massachusetts, and there are plenty of apple orchards in Massachusetts that are perfect for a fall day. Many of these local farms offer much more than apple picking, like Parlee Farms , a 93-acre farm in Tyngsboro, which also features a pumpkin patch and incredibly scenic views of the Merrimack River.

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Frost + Sun

12 Best Things to Do in Massachusetts in the Fall

By Author Meg Frost

Posted on Last updated: October 22, 2023

Categories Massachusetts , United States of America (USA)

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Grid of 4 photos, from L-R clockwise: Photo of a windmill with bushes with red leaves in the foreground, closeup of a pumpkin set amidst colorful mum bushes, closeup of an apple tree, and closeup of colorful mums. Text in the middle reads

Fall in Massachusetts is my favorite time of year in my home state. 

From the witchy, historic town of Salem to the beautiful Fall foliage colors, there is so much to do this time of year.

Keep reading for my local tips on the best things to do in Massachusetts in the Fall.

Celebrate all things marshmallow at What the Fluff

For those of you who aren’t New Englanders or have never heard of Fluff, Fluff is a spreadable marshmallow creme that was invented in Somerville, Massachusetts. 

This brilliant food is celebrated in a festival in Somerville each year called What the Fluff.

The festival includes music, Fluff-centric merchandise, food made with Fluff, and other fun activities.

In 2023, What the Fluff took place September 24 in Somerville’s Union Square. The 2024 date is not available yet.

Go back in time at King Richard’s Faire

Photo of a man and a woman dressed in opulent Renaissance garb at King Richard's Faire in Massachusetts.

Visit King Richard’s Faire, the largest Renaissance festival in New England, for a unique twist on Fall time activities.

King Richard’s Faire features Renaissance-themed food, drink, games, rides, music, contests, and other entertainment. And yes, there is a jousting tournament!

Employees and many visitors dress head-to-toe in Renaissance garb, adding to the fun.

In 2023, King Richard’s Faire will run on weekends from September 2 through October 22.

King Richard’s Faire 235 Main St, Carver, MA

Have fun at Massachusetts largest fair

Closeup of a cup of hard pumpkin cider from Harpoon Brewery booth at The Big E.

West Springfield, Massachusetts is home to Massachusetts and the New England region’s biggest fair, The Big E.

The Big E celebrates all things New England with rides, fun fair food, agricultural competitions and demonstrations, craft booths, concerts, and more.

There’s even a massive building dedicated to each of the New England states, Connecticut, Maine, Massachusetts, New Hampshire, Rhode Island, and Vermont.

In 2023, The Big E will run from September 15 through October 1. To learn more about this fun Fall fair, check out my post about The Big E .

Experience thrills and chills at Six Flags New England’s Fright Fest

Photo of 2 actors dressed as ghosts, acting out a scene with a coffin and a shovel.

If you’re in town for The Big E, make it a weekend trip so you can hit up Six Flags New England’s Fright Fest for some extra Fall-time fun.

On Fright Fest dates, Six Flag New England features haunted attractions, scare zones (including spooky characters on rides!), trick-or-treating, a dance party, and other Halloween-themed shows and entertainment.

In 2023, Fright Fest at Six Flags New England will run on select nights between September 23 – November 5.

Fright Fest @ Six Flags New England 1623 Main St, Agawam, MA

Celebrate Halloween in Salem, Massachusetts

Photo of a historic house and sailing ship along the Salem, Massachusetts harbor.

If you’re super into Halloween, there’s no doubt that Salem, Massachusetts is on your bucket list. 

This adorable small town sits just north of Boston and is known for its involvement in the Salem Witch Trials of 1692. 

Salem has embraced its notorious past and rebranded itself as a family-friendly Fall destination with its month-long Halloween celebration, Salem Haunted Happenings.

If you’re considering a visit to Salem, check out my post about Salem, Massachusetts in October , the best tours in Salem, MA , and the best things to do in Salem, MA .

Eat, drink & be merry at AppleFest

A fun way to see the gorgeous Fall colors in Massachusetts is at AppleFest, Wachusett Mountain’s mid-October festival.

AppleFest features food trucks, a farmer’s market, music, lumberjack demonstrations, craft vendors, and best of all, ski lift rides through Fall foliage.

In 2023, AppleFest will run on two weekends: October 14-15 and 21-22.

AppleFest @ Wachusett Mountain 499 Mountain Rd, Princeton, MA

Get your prep on at the Head of the Charles Regatta

Photo of a team of rowers gliding down the Charles River during the Head of the Charles race in Boston.

Don your preppiest Fall outfit and head over to the Charles River Esplanade to watch rowers from around the world compete in races.

The Head of the Charles is the largest 2-day rowing race in the world and features rowers and rowing teams from nearly all ages. 

While the focus of the race is, of course, the rowers and teams, the people watching is just as good!

In 2023, the Head of the Charles Regatta will take place October 20 – 22.

Shop ‘til you drop at SoWa Open Market

Photo of the Red Apple Farm market tent at SoWa Boston.

Get a jump on holiday shopping by shopping local at the SoWa Open Market. 

Open through October, the SoWa open market features local artisans, food trucks, music, and a beer garden. 

There’s also a farmer’s market with fresh produce, meat, and baked goods. Also nearby are lots of vintage shops and art galleries.

SoWa Open Market 530 Harrison Ave, Boston, MA

Drive the Mohawk Trail in Northwestern Massachusetts

Photo of a river lined with Fall foliage along the Mohawk Trail in Massachusetts.

The Mohawk Trail was originally a Native American trading route that enabled trade between Western Massachusetts and New York.

In 1914, it became one of the first scenic byways in New England. 

The 69-mile drive stretches along Route 2 between Greenfield, MA to the Massachusetts-New York border.

This northern Massachusetts scenic byway is a lovely way to see Fall foliage and some of the area’s best attractions, such as the Massachusetts Museum of Contemporary Art, concerts at Tanglewood, and the Berkshire Mountains.

Enjoy Massachusetts in the Fall on a day hike

Closeup of Bish Bash Falls in Massachusetts.

A classic Fall foliage activity in New England is doing a day hike to get epic views of the Fall colors. 

Here are 5 Massachusetts hiking trails to consider for a Fall foliage hike.

Arnold Arboretum Trail

The Arnold Arboretum Trail is perfect if you’re visiting Boston in the Fall , as it’s located in the Jamaica Plains neighborhood. 

This 3.7-mile loop trail takes you through Harvard University’s Arnold Arboretum, where you’ll see many different types of trees, plants, and flowers.

Bish Bash Falls Trail

For Fall foliage and a waterfall, check out the Bish Bash Falls Trail in Mt. Washington, MA. 

The 2.1-mile out-and-back trail takes you to Massachusetts’ tallest waterfall, Bish Bash Falls. 

For a longer hike, access the trail from the New York border, rather than from within Bish Bash Falls State Park. 

Cape Cod Rail Trail

The 26-mile paved Cape Cod Rail Trail can be picked up at a variety of points along the trail, so you can complete any length you want. It runs between Wellfleet and South Dennis.

This wide, paved trail is wheelchair accessible and also allows bikes and horseback riding. 

Mount Greylock Overlook Trail

This 2.4-mile, moderate-level hike has several gorgeous viewpoints primed for leaf peeping.

It is one of the most popular hikes during Massachusetts Fall foliage season, so plan ahead for traffic. Better yet, go during the week to help ease the weekend congestion on the roads.

South Sugarloaf Mountain Trail

Head to Mount Sugarloaf State Reservation in South Deerfield to hike the .6 mi out-and-back South Sugarloaf Mountain trail.

At the summit, you’ll see spectacular views of the Fall leaves across Massachusetts’ Pioneer Valley and parts of the Connecticut River.

Don’t feel like a hike? There’s also a road up to the top that is open til mid-October.

Walden Pond Path

Get inspired by the Fall foliage like Henry David Thoreau with a walk around the Walden Pond Path. 

The Walden Pond Path is a 1.7-mile loop around the famous pond, where you can also see Thoreau’s cabin. 

Most of the path is wheelchair accessible and if you contact Walden Pond State Reservation in advance, you can usually reserve an all-terrain beach wheelchair for use in the beach area.

The Innkeeper’s Loop Trail at Wayside Inn

The Wayside Inn Innkeeper’s Loop Trail is located in Sudbury, not far from Walden Pond. 

The 1.5-mile trail loops around Longfellow’s Wayside Inn, the oldest operating inn in the United States, and the surrounding area.

The Innkeeper’s Loop Trail takes you by Carding Mill Pond, a cider mill, the water-powered stone grist mill, and a historic 1-room schoolhouse.

Stay at the (likely haunted) Lizzie Borden house

Graphic of a vintage newspaper front page showing a drawing from the Lizzie Borden murder trial..

Rumor has it that Lizzie Borden killed her father and stepmother with an axe way back in 1892.

She was found not guilty, but the accusations and resulting bad reputation followed her to her death.

Today, the house where it all happened is preserved as a museum and inn. 

Yes, that’s right, you can spend the night at Lizzie Borden’s house! 

If you have the guts to stay in a haunted house, head over to The Historic Lizzie Borden House linked below to book your stay.

The Historic Lizzie Borden House 230 Second St, Fall River, MA

Get spooked at Massachusetts’ best haunted house

Located in Holyoke, DementedFX produces 2 immersive haunted experiences, the Bio Med Corp. haunted house and The Meat Tank zombie-themed experience.

In 2023, Demented FX starts Friday, September 29 and runs Friday through Sunday. The last date is October 29. It will also be open Thursday, October 26.

DementedFX 530 Main St, Holyoke, MA

What’s your favorite thing to do in Fall in Massachusetts?

Tell me about your favorite thing to do in Massachusetts in the Fall in the comments below.

For more fun things to do, check out these posts:

  • Fall in New England
  • Fall in the USA: Best Places to Visit
  • The Best Food Festivals in Boston, MA
  • 20 Fun Festivals & Events in Boston
  • I Dare You to Visit These Most Haunted Places in the US

About the author

Photo of travel blogger Meg Frost, of Frost + Sun, in Havana, Cuba.

Meg Frost is a Boston-based travel blogger that helps people embrace technology to make vacation planning and traveling wicked easy, affordable, and fun.

She holds an M.A. in Journalism from Northeastern University and B.S. in Communication & American Studies from University of Miami.

Read more →

This post was originally published September 5, 2021. It was last updated September 30, 2023.

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The Best Things to Do in New England in the Fall | Frost + Sun

Wednesday 2nd of November 2022

[…] out my posts about Massachusetts in the Fall, things to do in Boston, where to stay in Boston, tips for visiting Boston on a budget, and Boston […]

New England Wanderlust

Fall , Massachusetts  ·  June 14, 2023

31 Fun Things To Do In Boston In The Fall (2024)

Even though it’s New England’s largest city, there’s no shortage of fall coziness to be had in Boston! Offering the best of both worlds when it comes to big city amenities and quaint neighborhoods, Boston is one of the best places to visit in New England to enjoy the autumn season.

This post shares all my favorite things to do in Boston in the fall season, including where to find the best foliage displays, spooky Halloween activities, best festivals and parties, and even the best fall day trips from Boston. With that, let’s get started!

New England Wanderlust contains affiliate links, and is a member of the Amazon Services LLC Associates Program. We may earn a commission from any purchases you choose to make from our links, at no additional cost to you. For more information, please refer to our  Privacy Policy .

Is Fall A Good Time To Visit Boston?

Oh, absolutely! There’s just something extra magical about Boston in the fall season, and the city does an absolutely fantastic job capturing all the best things about this time of the year. You’ll find curated seasonal menus at the restaurants that highlight autumnal flavors, crunchy leaves on the sidewalks, parks filled with fall color, and so many things to do to fill up your itinerary.

On top of that, the fall season offers very comfortable weather. In the summer, Boston is hot . But once October hits, temperatures begin to drop, and while there can be the odd hot day, the weather is generally cooler and more pleasant for exploring the city. And since Boston is a great city to explore by foot, this just adds to the appeal of a fall visit.

Best Time To Visit Boston For Fall Foliage?

Mid-October is a great time to visit Boston for peak fall foliage, but honestly, the entire month of October will be beautiful. Early October will bring the first few peeks of the leaves changing, and by the third week of the month, the city is usually about as colorful as it gets. The color will typically last through Halloween, too.

But even after Halloween, you’ll usually find some colorful foliage still hanging onto the trees, and lots of it sprinkled all over the sidewalks.

However, one thing to know about fall foliage anywhere in New England, is that colors can peak at different times from year to year. The changing leaves is impacted by temperature and weather patterns throughout the entire year, so it doesn’t always happen at the same time. However, for Boston, mid-October is almost always a safe bet for the best fall color.

Where To See Fall Foliage In Boston

Let’s kick off my list on celebrating fall in Boston with where to find the best foliage around the city! Now, there are definitely more than these 3 places to see fall color, but I wanted to showcase the best of the best when it comes to colorful leaves. So these are the places you’ll want to visit on your autumn trip to Boston for foliage:

1. The Public Gardens

The Public Gardens in Boston are one of the best places to see fall foliage in the city.

If there’s one place to see fall foliage in Boston, it’s the Public Gardens. You’ll be able to enjoy colorful trees backdropped by the city skyline, take perfect fall photos on the pedestrian bridge, and see foliage at pretty much every turn in the park.

The Public Gardens are gorgeous year-round, too, so while they’re even more special in the fall, this is just a place that should be on anyone’s itinerary if you’ve never been.

Pro Tip : Many people hope to take a ride on the famous Swan Boats in the park, and while this is a really fun thing to do, they’re only open in the summer. They typically shut down right after Labor Day, so this isn’t something you should plan on doing during your fall trip. However, definitely plan to enjoy the rest of the park during this beautiful season!

2. Boston Common

The Boston Common is the fall season is always filled with gorgeous foliage colors.

Right next to the Public Gardens is Boston Common, which is another wonderful park in the city that’s a great spot to enjoy fall foliage colors. While The Common isn’t quite as picturesque as the Public Gardens, you’ll find walkways and lawns at this park filled with fall color.

And since it’s just steps from the Public Gardens, it’s so easy to see them both at the same time.

3. The Esplanade

The Charles River Esplanade in Boston is a 3-mile waterfront path that's especially beautiful in the fall season.

One of my favorite walks in Boston year-round is the Esplanade, and it’s definitely the best in the fall season. A paved walkway along the Charles River, the Esplanade is packed with foliage color in the fall, and is such a lovely place to enjoy a crisp, autumn walk.

Stretching over 3 miles, you can really walk for a while here, too, and there are fun places to stop along the way. If you don’t want to walk the whole thing, it’s easy to exit and head back into the city when you’re ready. And if you’re looking for things to do along the path, I recommend visiting the floating dock, and admiring the street art (there are both permanent and seasonal displays to check out!).

Spooky Tours To Take In Boston In The Fall

While most of these tours are offered year-round in Boston, a spooky tour is always better in the fall, right? With Halloween approaching, fall decorations everywhere, and the cool night air, all of these things combined just beg you to book a fun haunted tours in one of the country’s most haunted cities!

4. Ghosts & Gravestones Trolley Tour

The Ghosts & Gravestones Trolley Tour is one of the most popular in the entire city, and for good reason! You’ll hop aboard a trolley at night to cruise around Boston with a costumed guide, and learn all about the spookiest hauntings around the city.

Sites you’ll see along the tour include the Boston Tea Party, the historic North End, and you’ll even get off the trolley to walk through the city’s oldest burial grounds for all the goosebumps and chills you could want.

🍁 Click here to check out the Ghosts & Gravestones Trolley Tour

5. Haunted Pub Walking Tour

The Haunted Pub Tour is perfect for those looking for a good mix of fun, history and a few scares. This walking tour takes you to some of the city’s most haunted pubs, where your expert guide will share spooky stories of ghost sightings. During each pub visit, you’re also welcome to purchase a drink to enjoy while learning about the haunted happenings.

This tour also passes by Beacon Hill, King’s Chapel, and Granary Burying Ground for all the spooky stories you could possibly want between your visits to the pubs.

🍁 Click here to check out the Haunted Pub Tour

6. Death & Dying Walking Tour

The Death & Dying Tour is perfect for those looking for an eerie walking tour through the city that tells the tales of the most haunted places in Boston. This tour is so spooky, that it’s an adult-only event that takes place at nighttime.

🍁 Click here to check out the Death & Dying Tour

Fun Things To Do In Boston In The Fall

For more fun things to do in Boston in the fall season to celebrate everything that this season is about, check out some of these recommendations below:

7. Sip On Seasonal Brews

Boston is such a great city for crafts breweries, and in the fall, you can take advantage of all the fun seasonal flavors that are special releases.

My favorite brewery to visit in Boston is Trillium Brewing , and in the fall, their Barrel Aged Spice Cake Imperial Stout is to die for. They often have fun cocktail creations in the fall season, too. Trillium also has a few Beer Garden locations around the city, including the Greenway, Fenway and the Common. Check out one, or all of them – I won’t judge 😉

Another popular place for local beer in Boston is Harpoon Brewery , and their Flannel Friday is the one you’ll want to order in the fall.

8. Order Some Seasonal Cocktails, Too!

In addition to seasonal craft brews, you’ll also want to check out all the awesome seasonal cocktails that are poured around the city! Infusing drinks with apple, maple, and ginger, this is a great way to savor the flavors of the season before heading out to dinner.

A great place to check out is the Boston Harbor Distillery , which has a really fun cocktail bar that serves up creative drinks with seasonal specials. While here, you can also book a tour of the distillery and get a behind-the-scenes look at how their liquors are made.

Later in the post, I recommend staying at the Boston Harbor Hotel, and if you happen to book a room there, you won’t have to stray far for a great cocktail! The Rowes Wharf Bar does an awesome job with fall-inspired drinks that incorporate the flavors of the season.

Other great places for cocktails in Boston are Next Door Speakeasy , Hecate , and Birds of Paradise .

9. Enjoy The Last Whale Watch Tours For The Year

The fall season brings the last of whale watching in the New England region, and you can actually head out on a whale watch tour right from Boston! Whales have usually migrated too far south once October is over, so if one of your goals was to spot some whales this year, book your tour before Halloween!

Whale Watch tours from Boston visit the word-famous Stellwagen Bank Marine Sanctuary, which is where the tours from Provincetown on Cape Cod go – so you’re definitely going to the best place in New England on these tours.

Tours in Boston typically depart from Long Wharf along the waterfront area, and last for about 3.5-4 hours. And since it’s the fall season, you’ll want to be sure to bundle up, as the air will be much colder out on the water. I’d recommend packing a beanie, a warm coat, and even some gloves to stay warm.

🍁 Click here to check prices & availability for whale watching from Boston

10. Try ALL The Chowders

I love a good cup of New England clam chowder year-round, but man, is it even better in the fall and winter! The chilly air makes you appreciate a warm, creamy cup of chowder even more, so whether it’s your first-ever cup of chowder in the area, or you’re a seasoned pro, it’s one of the best things to have in Boston in the fall.

One of my favorite places for both seafood and chowder in Boston is the famous Union Oyster House . This is a popular place that some may call touristy, but honestly, I think it lives up to its reputation. First-time visitors will love the vibe here, as well as the selection of wonderful, fresh seafood. And this is a place where you don’t want to skip the clam chowder!

Walrus & Carpenter Oyster Bar , Neptune Oyster , and Atlantic Fish Company all also have incredible cups of chowder!

🍁 Want to try the best of Boston’s food? I recommend booking a food tour! Click here to check out my round-up of the best Boston food tours!

11. Get Cozy At Beacon Hill Books & Café

View this post on Instagram A post shared by Beacon Hill Books & Cafe (@beaconhillbooksandcafe)

What is it about fall and wanting to throw on a blazer, sharpen pencils, and crack open a good book in the fall season? If those vibes are up your alley, you’ll want to add a trip to Beacon Hill Books & Café to your itinerary.

A new addition to Boston, this bookshop is equal parts cozy and Instagram-worthy. It just so happens to also be a place you’ll probably never want to leave if you love books and a warm drink on a fall day.

The entire store is designed to make you feel like you’re browsing someone’s personal library in their historic home, but the selection is absolutely never-ending. You’re pretty much guaranteed to find your next great read during your visit.

The on-site café is about as picturesque as it gets, and serves breakfast, lunch and lite bites for dinner, as well as an afternoon tea on Sundays.

Since opening, this place has gotten rather popular, so I recommend booking a table online in advance to ensure you can snatch up a table. I suggest arriving an hour early so you can pick out a new book to start reading, purchase it before your reservation, and then spend a cozy afternoon in the café with delicious food and a great, new book.

12. Take A Crisp Fall Walk In Beacon Hill

Acorn Street in Beacon Hill is one of the most famous and picturesque streets in the entire city. This is one of the places to see in Boston in the fall.

Great news! Beacon Hill Books is located in probably the cutest and coziest neighborhood in Boston, so before or after your visit to the bookstore, budget some time to explore the cobblestone streets of Beacon Hill.

In the fall season especially, this entire neighborhood feels like a New England postcard. You’ll spot fall foliage, historic streets, gorgeous brownstones perfectly decorated with pumpkins on their stoops, and cute little boutiques with lovely fall window displays. This is a great place to just wander, and take in all the fall vibes. Just be sure to have your camera ready at all times – you’ll need it 😉

13. Pick Up Fall Treats At Tatte Bakery

View this post on Instagram A post shared by Tatte Bakery (@tattebakery)

One of the most popular bakeries in Boston is Tatte Bakery & Café, and honestly, it’s worth waiting in line in the fall season for one of their apple pastries! I’m in love with their apple turnovers, which are the perfect fall treat on a crisp day. They also offer up great spiced lattes in the fall season.

Grab one of these to go to snack on while you explore Beacon Hill, or plan to stay a while and have breakfast or lunch at the café. The interior of each location is so stunningly beautiful, so it’s worth it to linger and enjoy the atmosphere.

In the fall season, they have other delicious goodies like homemade maple pecan pie, pastries infused with cinnamon and pumpkin flavors, and savory dishes spiced with cardamom. It doesn’t get much better than that, right?

14. See The Giant Pumpkins At Boston Public Market

The Boston Public Market is a great stop to make year-round, and in the fall season, you’ll want to swing by to check out the giant pumpkins that are on display for your dose of autumnal fun.

But the fun doesn’t stop there at the Market! The second half of October brings some fun events like the Urban Pumpkin Patch, Pumpkinpalooza, Pumpkin Vase Flower Arranging, and a Taste of the Season food event. If any of these sound like they’re perfect for your itinerary, check them out here before visiting!

15. Join A Walking Tour

Boston is one of the most charming and historic cities in the entire country, and an easy way to get to see all the best places if it’s your first time is by joining a walking tour. There are all kinds of wonderful tours to check out in the city that cover everything from history, the Freedom Trail, to food tours (mentioned earlier!).

The fall season is actually my favorite time to take a walking tour because of the more mild weather, so grab your scarf and sneakers, and get out there to see all the amazing historic places around Boston this fall.

Here are some of the best walking tours around Boston:

  • Small Group Freedom Trail Tour
  • Revolutionary Story Walking Tour
  • Boston History & Highlights Tour

16. Enjoy Foliage Views On A Cruise

One of the best ways to enjoy Boston in the fall season is to take in views of the skyline from the harbor, and good news! There are some awesome cruises available to help you plan the perfect day.

My favorite, however, is this sunset cruise , because there’s just something so dreamy about seeing the fall colors enhanced by the amber glow of the setting sun. On board, have your camera ready to snap photos of the skyline during the best time of the day. And drinks and snacks are also available on the boat to make your trip even more fun.

🍁 Click here to check out this wonderful sunset cruise in Boston

17. Experience The Arts During Doors Open Day

For anyone out there hoping to get their fill of arts and culture on their fall trip to Boston, you’ll want to pay attention to this one. Every October, the Fenway Alliance coordinates a special Doors Open Day, where over 80 cultural experiences can be enjoyed at absolutely no cost.

The event changes from year to year, and has only continued to grow since its inaugural event in 2001. But past events have included dancers, art exhibits, concerts, and so much more.

18. Stroll Around Harvard Campus

Harvard University is one of the most fun places to tour when visiting Boston.

Like I mentioned earlier in the post, fall always makes me want to buy a new blazer, throw on some loafers, and feel like a student again … maybe without the classes and homework 😉 If you share the same sentiments, then a tour around the historic Harvard University campus may be something you’ll enjoy!

Having walked around Harvard myself, I can honestly say it’s such a cool thing to do when visiting Boston, especially in the fall season for all those back-to-school vibes.

And while you can definitely just walk around the campus on your own, you can also book a really fun and quick tour that’s led by actual Harvard students. Get the inside scoop on what life is like on campus, find all the prettiest buildings, and listen to entertaining stories from your guides along the way.

🍁 Click here to check out the guided Harvard Campus tour

Awesome Fall Day Trips From Boston

While there’s so much to do right in Boston proper in the fall season, there are some amazing places nearby that are especially magical in the fall. These are the destinations I recommend if you’re looking to add a day trip or two to your fall Boston itinerary:

19. Salem, Of Course!

Salem, MA is one of the best day trips in the area in the fall season, especially in October for all their Halloween events.

If you only have time for one fall day trip from Boston, it’s just got to be Salem, right?! I mean, it’s really the heart of all things Halloween in New England, and through the month of October, it’s one of the most exciting places to be for all things spooky.

During your day trip, you can join a Hocus Pocus filming locations tour or a spooky ghost tour (or both!), visit the Salem Witch Trials Memorial, and participate in all the fun Halloween events that take place all month long during Haunted Happenings.

The best way to visit Salem for a day trip is to take the ferry from Boston. Salem in October is, well … crowded. And parking will be a challenge, for sure. Leaving your car behind is a good idea during this time of the year, and since Salem is pretty small and walkable, you won’t have to worry about getting around on foot.

The ferry also takes less than 1 hour to get to Salem, so by the time you drive out of the city and find parking, it’s probably faster to just take the ferry.

🍁 Click here to check out the Boston → Salem ferry

Pro Tip : When you book your tickets, be sure to book both your ride to Salem, and your return trip back to Boston. Prices reflect a one-way ticket only!

Psst! I have some helpful guides including planning the perfect Salem, MA day trip , and the best time to visit Salem if you need more information 😉

20. White Mountains In New Hampshire

A great tour option from Boston, especially for those who plan to use Boston as their home base for their fall trip, is this awesome fall foliage tour through the White Mountains in New Hampshire . Taking all the guess work out of planning your own trip there, this tour does it all for you.

It’s a long day at around 12 hours, but you’re going to see the best of what New Hampshire has to offer in terms of fall foliage in one easy day trip. An expert guide takes you to some of the best spots for foliage in the area, including the famous Kancamagus Highway, North Conway, and the iconic Omni Mount Washington Resort (which is rumored to be haunted!).

🍁 Click here to check out this awesome tour to the White Mountains From Boston!

21. Newburyport

The waterfront part is one of the best things to see in Newburyport.

One of my personal favorite fall places to visit that’s close to Boston is Newburyport. This little city feels more like a quaint, small town, and has amazing shopping and dining, waterfront scenery, boat tours, and of course … fall foliage. To me, it feels like the set of a Hallmark movie.

Visiting from Boston is pretty easy, too. There’s a commuter train that goes right to Newburyport, and it takes just over an hour to get there. It drops you off about a 30-mins walk from the heart of town in Newburyport, but you could enjoy the walk on a nice fall day, or call a taxi (Ride Share services up this way are hit and miss).

To go at your own pace, I’d recommend renting a car to drive up to Newburyport, though. You can easily spend the day here, but there are some fun stops to make along the way, including Rockport for coastal charm. And you could choose to continue up to Portsmouth, NH for more fall foliage, and a cute town atmosphere.

22. Sturbridge

Sturbridge, MA in the fall season is one of the best places to see foliage on a New England fall road trip.

An amazing place for fall foliage and cozy vibes is Sturbridge, MA, which is just over an hour outside of Boston. Famous for Old Sturbridge Village, which is wonderful year-round, it’s especially stunning in the fall season. This cute little town is also home to some wonderful parks for relaxing nature walks, a nice apple orchard, and Altruist Brewing Company.

23. Concord

Concord, MA is a wonderful day trip from Boston in the fall season.

Lastly for charming towns near Boston for cozy fall vibes and foliage, you’ll want to check out Concord. Located less than hour outside the city, it’s famous for its American Revolutionary War sites, and of course, Louisa May Alcott’s family home.

While all these things are worth checking out, it’s especially beautiful in the fall season with all the lovely foliage color at every turn. You’ll find historic homes lining the streets and bright red and orange leaves on all the trees. This is a great escape from Boston if you’re looking for small-town charm, history, and postcard-worthy moments.

24. Plymouth

Brewster Gardens in Plymouth, MA in the fall season.

Just under an hour from Boston, Plymouth makes for the ultimate fall day trip from Boston in November for their Thanksgiving celebrations. As the fall season comes to an end, there’s still so much to do in Plymouth throughout November, as they celebrate the holiday with lots of special events and fun things to do.

Plus, it’s good to know that Plymouth is one of the last places in New England to experience peak foliage, so if you happen to visit the first half of November, there’s a good chance you’ll get to see some vibrant fall color.

In November, Plymouth celebrates its historical significance with a Thanksgiving parade the weekend before the holiday, exciting music performances and concerts, a harvest market, and a really fun waterfront festival with food trucks, beer and wine gardens, and children’s activities.

But the coolest thing to check out in November is the traditional “Story of Thanksgiving” dining experience at the Plimoth Patuxet Museum, which includes a full dinner, as well as actors playing the part of Pilgrims, who tell stories about what life was like during the early settlement.

Psst! I have an entire post on things to do in Plymouth, MA that make it worth visiting , if you’d like more ideas for your fall day trip 😉

25. Visit A Haunted House

While there are no haunted houses right inside the city of Boston, there are some really great ones to check out nearby!

One of the most famous haunted attractions in Massachusetts is the Lizzy Borden House in Fall River, which is about an hour outside of Boston. Ghost tours are given inside the original home, and you can even book an overnight stay if you’re looking for the ultimate thrill.

There are several other haunted houses and attractions nearby – I have an entire post on these to help you pick the best one for you, so be sure to click on that link below (at the end of this section).

26. Experience The Davis Mega Maze

Located in Sterling, which is just about an hour outside of Boston, you’ll find the very fun Davis Mega Maze. This corn maze spans over 3 miles and 8 acres, and can take anywhere from 30 minutes to 3 hours to finish, according to their website! So, you can really make an entire day out of it.

During the month of October, they really make their farm a fun destination, too, and you’ll find live music, craft beer and drink vendors, awesome food vendors, zip lines, camp fires, and special Halloween events. If you’re looking to plan the ultimate fall day of fun from Boston, this is the place to go.

Here are some posts to help you plan your fall day trips from Boston:

  • The Ultimate Salem, MA Day Trip Guide
  • Best Haunted Houses & Places To Check Out In Massachusetts
  • Best Things To Do In Newburyport, MA

Fall Festivals & Events In Boston

27. titanic masquerade halloween yacht party.

For the ultimate Halloween party on the water, you’ll want to snatch up your tickets to the Titanic Masquerade Halloween Yacht Party ASAP! This party takes places on the Spirit of Boston, and cruises along Boston Harbor at night.

Climb aboard in your best Halloween costume, and enjoy 4 decks of fun. The party is led by the best DJ’s in Boston, so you can dance the night away while taking in the best nighttime skyline views.

28. Head Of The Charles Regatta

One of the most famous fall events in Boston is the Head of the Charles Regatta, and while it takes place in nearby Cambridge, it’s so easy to experience during a fall trip to Boston.

This regatta is actually the world’s largest 2-day rowing event, and this is where the best of the best compete in rowing championships along the Charles River. It’s such a fun thing to experience in person, and because the views of the river are so special in the fall season, it’s also a great way to enjoy autumn in Boston!

29. Harpoon Dogtoberfest

Okay, so probably the cutest fall event in Boston is the Harpoon Dogtoberfest, which is held in October each year.

If you’re traveling to Boston, you probably won’t have your furry friend with you, but that doesn’t mean you can’t be an enthusiastic spectator 😀 And if you’re in the Boston area, I encourage you to participate!

During Dogtoberfest, participate in a pup costume contest, or a 3-mile walk/run/trot/jog – whatever your pup’s speed is. Proceeds from the event go toward local charities, and honestly, what’s not to love about giving back AND seeing dogs in costume?

Bonus: Harpoon Octoberfest (For Humans 😉)

Looking for the human version of Octoberfest at Harpoon? I’ve got you covered! There’s one of those, too. Usually in late September, the brewery hosts this event, and has live music, plenty of beer, lots of food, fun contests, and tons more.

30. Harvard Square Oktoberfest

For over 40 years, the Harvard Square Oktoberfest has been a fall tradition in the Boston area. While the Harpoon Octoberfest is for those 21+ only, the Harvard Square Oktoberfest is a family-friendly event that appeals to everyone.

Enjoy awesome food vendors, live music, craft vendors and lots more!

31. Boston Public Market Harvest Party

Lastly, a wonderful fall event to have on your radar is the Boston Public Market Harvest Party, which also takes place in October each year.

During the Harvest Party at the Market, enjoy bites from local vendors, craft drinks featuring local spirits, live music, and an array of awesome vendors. Proceeds of the event go toward the Community Engagement Fund, which is a local organization that works to offer free events at the Market.

Where To Stay In Boston

Boston Harbor Hotel : For a high-end stay, this 5-star hotel on the waterfront is hard to beat. With on-site dining that includes an awesome cocktail bar, a pool, and gorgeous rooms , it has everything you need for a relaxing fall getaway.

🍁 Click here to check out the Boston Harbor Hotel

Revere Boston Common : A great location that’s just steps from Boston Common, Beacon Hill, and the Public Gardens . There’s also a fun rooftop bar, on-site dining, free admission to the Paul Revere House, and modern rooms .

🍁 Click here to check out the Revere Boston Common

The Godfrey : Also a great location that’s a short walk to Boston Common, Beacon Hill and the Public Gardens. The plaid headboards in the modern rooms are the perfect fall decor for your trip, and they also have Polaroid camera available for guests to use during their stay!

🍁 Click here to check out The Godfrey

Fall Weather In Boston

As mentioned earlier in the post, fall is one of the best times (if not the best) to visit Boston. The weather will likely be perfect. While you’ll want to anticipate some warmer weather, especially if you visit earlier in October, you can generally expect very comfortable temperatures ranging from 60-65°F.

You’ll also want to prepare for rain on a fall Boston trip, as October and November both have about 7-9 days of rain per month. However, it’s very possible you could luck out and have sunny weather the entire time.

I mention this in almost all my posts about weather in New England, but it bears repeating – weather in this region is moody, and changes frequently. So it’s best to check weather reports a few days before leaving to get a better idea of what to expect during your trip.

The brownstones in Beacon Hill are always perfectly festive during the fall in Boston.

Is Boston In The Fall Season Expensive?

Unfortunately, yes, as are many New England destinations in the fall season. Boston is an expensive city year-round, but factor in fall foliage and its proximity to Salem, and you’re very likely to see price jumps in hotels. Expect to pay about $250-$350+ per night at a hotel in Boston.

You can, of course, find deals outside of the city, but even in Cambridge, it’s going to be higher than most other places around the country.

What To Pack For Boston In The Fall

Here are some helpful things to add to your packing list for your fall trip to Boston:

  • Waterproof sneakers or boots in case of rain
  • In fact, unless you plan to visit really fancy restaurants, I would leave your heels at home. Boston is a pretty casual city, and with the uneven cobblestone streets in many areas, a cute pair of booties will do the trick for pretty much any occasion.
  • A nice, casual dress and jacket will work perfectly for a dinner out (again, unless it’s a very fancy place with a dress code, which is unlikely).
  • A rain jacket that’s waterproof.
  • Sweaters and jeans – this is what I usually live in when visiting Boston in the fall season.
  • If you’re anticipating both warm and cool weather, pack some t-shirts that you can wear under sweaters to create light layers.
  • Beanies and scarves if it’s forecasted to be cold.
  • Reusable water bottle to stay hydrated while you walk around.
  • Dramamine if you’re planning on a whale watch or cruise, and tend to get seasick.
  • Day pack for any day trips you’re planning.

More posts you may also enjoy:

  • Your Ultimate Guide To New England In The Fall
  • Best Things To Do In Massachusetts In The Fall
  • Best New England Ghost Tours
  • The Perfect New England Fall Road Trip Itinerary
  • Best Stops To Make On A Boston To Stowe, VT Road Trip
  • Is New England In November Worth Visiting?
  • Thanksgiving In New England: Cozy Getaway Ideas & Things To Do!

That’s A Wrap On Things To Do In Boston In The Fall

And there you have it! All my insider tips on the best things to do in Boston in the fall. Whether you’re using Boston as the starting point for an epic fall trip around New England, or it’s the home base for your trip, there are so many wonderful fall things to do that allow you to embrace the very best things about this magical time of the year. 🍁🍂🍁

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Armstrong Farm is one of the most fun pumpkin patches in Vermont to visit in the fall!

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10 Beautiful Stops On A Massachusetts Fall Foliage Road Trip

massachusetts towns to visit in fall

  • Activities and Interests
  • Destinations
  • Fall Travel
  • Massachusetts
  • Road Trips In The U.S.
  • Seasonal Travel
  • Types of Travel
  • United States

Each and every September, Massachusetts proudly shows her colors. Burnt sienna, crimson red, and tawny yellow dance around swaths of evergreen, creating a palette that draws you in. The annual passing of summer and onset of autumn shine brightly in New England’s foliage .

Leaf peeping is not always about riding in your car. A drive can provide glorious views, but if you explore the region on foot, you will find yourself literally immersed in the colorful canopied wonderland.

The foliage season in Massachusetts begins in mid-to-late September and typically peaks around Columbus Day. The peak moves west to east across the state, as will our fall foliage road trip.

1. Lake Mahkeenac

Stockbridge.

Stockbridge , home to the Norman Rockwell Museum , is a picturesque New England town and the ideal spot to start your fall foliage road trip. Located in the Berkshires , Stockbridge is dotted with family farms and tree-lined country roads. It is the perfect place to take a leisurely drive to nowhere and see where it takes you.

Travel down Route 183 and stop at the Stockbridge Bowl , also known as Lake Mahkeenac. The 372-acre lake provides a spectacular backdrop for photos of the forest’s autumn colors. When the morning sun hits the still lake and the vibrant hues of the trees are reflected in the water, you will be happy you set your alarm and grabbed a to-go cup of morning joe. Photographers come from near and far to capture Lake Mahkeenac’s peaceful beauty in autumn.

Bash Bish Falls in Massachusetts in autumn

2. Bash Bish Falls

South egremont.

Head south about 10 miles to the highest single-drop waterfall in Massachusetts, Bash Bish Falls . The spectacular landmark hemmed in by rocks and framed by delicate, colorful maple trees is worth the hike.

There are two popular options to get to the falls. You can park in Bish Bash Falls State Park’s Upper Falls lot and climb down along the falls, but this can be a little slippery at times. Alternatively, you can park in the lower lot and hike up the Bash Bish Falls Trail , an easy 2.1-mile out-and-back hike.

3. Canyon Ranch Wellness Resort

Heading north, Lenox is situated on Route 183. The famous Canyon Ranch Wellness Resort is a luxurious retreat waiting to help you relax and rejuvenate.

Canyon Ranch offers traditional spa services, including massages and skin care. They also offer wellness services like spiritual wellness and life management sessions. It is the perfect place to center your mind and body as you celebrate the changing seasons.

The resort’s grounds are meticulously maintained and beautiful in the fall.

Views from Mount Greylock during the fall.

4. Mount Greylock State Reservation

Lanesborough.

If you are searching for a view, head to the Mount Greylock State Reservation , one of the best leaf-peeping spots in the state. At 3,491 feet, it’s the highest peak in Massachusetts and offers a truly spectacular panoramic view. Showcasing the annual riot of crimson, yellow, orange, and green better than almost any other spot, Mount Greylock is a stop that should not be missed.

If hiking to the top sounds intimidating, you can skip the exercise and drive up the auto road to the summit. Enjoy a meal at Bascom Lodge or pack a picnic lunch and a blanket. Then sit back and enjoy the incredible view.

If you feel like becoming one with the foliage, jump on the Appalachian Trail for a hike.

The Mohawk Trail State Forest during fall.

5. Mohawk Trail State Forest

The Mohawk Trail State Forest is composed of 6,000 acres of mountains, gorges, and woodlands with the Deerfield River running through it. The trail is an old Native American path connecting the Connecticut and Hudson River Valleys.

You can choose from several excellent trails to explore in the area. The Mahican-Mohawk Trail to Indian Trail Loop is a 4.7-mile moderately rated hike. The payoff is the stunning view from the top of Indian Trail.

Sawmill Old Sturbridge Village MA

6. Old Sturbridge Village

The Old Sturbridge Village offers history in addition to beautiful fall foliage. Leaves rustle and crunch as you walk the old carriage paths. The costumed historians bring colonial times to life, enacting stories of early settlers and their lives in New England. Explore the village shops and homes while docents explain Early American crafts.

Finish your visit with a meal at the Publick House Historic Inn & Country Lodge . Think roasted native turkey, cornbread stuffing, and deep-dish apple pie — essentially, New England on a plate. The Publick House Historic Inn is a step back to 1771, with its 18th-century charm paired with modern-day touches. If you are looking for a fun place to stay the night, the inn offers four distinct options, including the main Publick House Historic Inn and the Country Lodge.

7. New England Botanic Garden At Tower Hill

New England Botanic Garden at Tower Hill is one of the prettiest places in Massachusetts to enjoy fall foliage. With views of the Wachusett Reservoir and Wachusett Mountain, the garden is breathtaking, providing ample photo opportunities.

Quiet corners and strategically placed benches are the perfect places to enjoy some personal reflection.

Historic Major John Buttrick House in Minute Man National Historical Park, Concord, Massachusetts, USA.

8. Minute Man National Historical Park

Welcome to the birthplace of the American Revolution. Minute Man National Historical Park is a fun place to explore for people of all ages. Old carriage roads lined with hand-stacked stone walls meander around the park.

Sign up for one of several guided tours and watch the fight for American independence come to life. At Hartwell Tavern, a minute man will regale you with stories of the local militia and demonstrate how to fire a musket. You can also tour The Wayside, home to three famous authors: Louisa May Alcott, Nathaniel Hawthorne, and Harriet Lothrop.

Next, walk the Battle Road Trail , where the Battles of Lexington and Concord took place on April 19, 1775. The 9.1-mile trail will take you through fields and forests, bringing you back in time to the American Revolution. Since it is an out-and-back trail, you can easily make the hike shorter. The wide, shaded paths are breathtaking when covered in brightly colored fallen leaves.

Fall foliage at Arnold Arboretum in Boston, MA

9. Arnold Arboretum At Harvard University

Continuing eastward, Arnold Arboretum is a 281-acre preserve designed by famous landscape architect Frederick Law Olmsted. With more than 17,000 plants, the arboretum is an outdoor museum of sorts. The riot of color in autumn is unsurpassed, considering that each plant offers its own unique leaf show.

11 Affordable Boston Vacation Rentals For Budget Travelers

Bring your camera and your curiosity. You will see plants you have never seen before. The arboretum offers app-guided tours. The Explorers Garden Tour is a quarter-mile tour through the garden, highlighting specimen trees like the Chinese stewartia and the dove tree.

Fall foliage in the Boston Public Garden.

10. Boston Public Garden

No fall foliage road trip through Massachusetts would be complete without a stop at the Boston Public Garden . Lush green lawns, the lagoon with its swan boats, 80 species of plants, and winding walking paths — this is the place where Bostonians relax. Find a takeaway joint and grab a picnic lunch, lay out a blanket, and read a few chapters of a great book on a crisp autumn afternoon.

Stop by to see the Make Way for Ducklings tableau, sometimes seasonally dressed in Boston sports gear. Modeled on those from the beloved Robert McCloskey book, the ducklings are near and dear to every Bostonian’s heart.

Enjoy a leisurely 15-minute ride on the swan boats . They are part of Boston history and a memorable addition to any visit.

Foliage season is high season for many Massachusetts resorts. If you are looking for a specific spot to stay overnight, reservations will most likely be required several months in advance. Pack layers of clothing, since the temperature can vary from warm to chilly.

Related Reading:

  • 11 Best Fall Foliage Getaways In New England
  • The Most Scenic New England Fall Foliage Road Trip
  • 15 Best Stops During A New Hampshire Fall Foliage Road Trip

Image of Sandi Barrett

Sandi loves writing about culture, cuisine, adult beverages, cruising, golf, skiing, road trips, hiking, New England, and photography. Traveling solo, with hubby Chris, or the entire Barrett clan there is always a story waiting to be told.

PlanetWare.com

15 Best Places to Visit in Massachusetts

Written by Barbara Radcliffe Rogers Updated May 13, 2023

The sheer variety of experiences and tourist attractions in Massachusetts will astonish you. Boston itself combines the vibrancy of a modern university town and commercial city with treasured historic sights. Plymouth preserves - and recreates - the experience of New England's earliest settlers. Throughout the state, you can visit the homes and studios of some of America's most beloved writers and artists: Louisa May Alcott, Thoreau, Whistler, Longfellow, Melville, Norman Rockwell, and Daniel Chester French.

But the places to visit in Massachusetts are not all about culture and history. Whether you head for the ski trails of the rolling Berkshires in the west or the long white sands of Cape Cod and Martha's Vineyard , Massachusetts is about kicking back and having a good time, too. Plan your trip with our list of the best places to visit in Massachusetts.

2. Cape Cod

3. cambridge, 4. nantucket and martha's vineyard, 5. salem and cape ann, 7. lexington, 8. plymouth, 9. the southern berkshires, 10. mohawk trail and the northern berkshires, 11. worcester and old sturbridge village, 12. new bedford and fall river, 13. amherst and the pioneer valley, 15. newburyport and plum island, map of places to visit in massachusetts.

Boston

From the Brahmin bastion of Beacon Hill and the historic sights of the famed Freedom Trail , to the world-class art museums , "The Hub" has something for everyone. Whether your passion is fine art, ethnic neighborhoods, Americana, antiques, seafood, modern architecture, black history, music, the Revolution, technology, bookstores, boats, brownstones, boutiques, or baked beans, you'll find it here.

Tourists interested in history can start their tour of the Freedom Trail at Boston Common , where you can get self-guided tour information or sign up for a tour led by a costumed interpreter at the Visitor Center . Highlights of the tour are the State House , Old South Meeting House , Paul Revere House , Old North Church , and Bunker Hill Monument . Tourists can also explore areas like the North End , a walkable neighborhood that is home to many historic sites (and several excellent pastry shops).

Boston is a great city for families, offering plenty of attractions that interest all ages . The Waterfront district is a great place to start, home to the New England Aquarium and the Christopher Columbus Park . The famous Faneuil Hall Marketplace is only a five-minute walk from here, offering a huge range of dining options, including a food hall, as well as tons of shops and cart vendors. Families also love the Boston Museum of Science , home to a planetarium, IMAX, and many interactive exhibits.

Younger kids always adore the Boston Children's Museum , which is full of activities and playful learning, and any summer visit with kids needs to include a ride on the Swan Boats in the beautiful Boston Public Garden .

Cape Cod

Reaching out into the Atlantic south of Boston, Cape Cod is the city's summer playground, with miles and miles of white-sand beaches and picturesque towns filled with tourist attractions and amusements.

For active travelers, the Cape offers sailing, fishing, kayaking, swimming, and miles of cycling and walking trails. Nature lovers find bird-filled salt marshes, and whales to watch in the nearby waters of Stellwagen Banks. The seafood is legendary, and in the fall, entire landscapes are red with cranberries.

A 40-mile stretch of Cape Cod's eastern coast is set aside as Cape Cod National Seashore , its perfect dune-backed beaches, woodlands of Atlantic white cedar, and bird nesting grounds networked by miles of hiking paths. At the outer tip of the cape is lively Provincetown , known for its inclusive atmosphere and thriving arts scene, including live drag shows during the summer. Tourists also venture to the far end of the cape to see the impressive dune system.

View of Harvard University

Although part of Boston's metropolitan area and connected by a single transit system, Cambridge is a separate city. And within it are two premier universities whose campuses feel like cities of their own. Harvard is the country's oldest institution of higher education, dating from 1636, only 16 years after the Pilgrims landed at Plymouth. The campus, which you can tour free with a lively student guide, is centered in Harvard Yard , right at Harvard Square .

Adjacent are the outstanding Harvard Art Museums , in a building designed by Renzo Piano, and farther on is the complex housing the equally prestigious Peabody Museum of Archeology and Ethnology; Mineralogical Museum; and the Botanical Museum, housing the famous collection of glass flowers.

The 150-acre Massachusetts Institute of Technology (MIT) campus is an open-air art gallery, with sculptures by artists that include Pablo Picasso, Alexander Calder, Henry Moore, Jacques Lipchitz, and Auguste Rodin. Discover these with the help of a campus map, as you stroll among buildings designed by some of the greatest names in modern, postmodern, and contemporary architecture: Frank Gehry, Alvar Aalto, I. M. Pei, and Eero Saarinen, among others.

Gay Head in Martha's Vineyard

South of Cape Cod and easy to reach by ferries, Nantucket and Martha's Vineyard offer sandy beaches and the relaxed pace of island life. Nantucket is a 15-mile-long island only 30 miles south of Cape Cod. Between 1740 and 1830, more than 125 whaling ships called Nantucket their home port, making it the world center for the whaling industry.

You can discover more about whaling, whales, and the ships and seamen who hunted them, at the Nantucket Whaling Museum , filled with ship models, scrimshaw, whaling equipment, fascinating logbooks, and the skeleton of a 43-foot sperm whale. Elsewhere on the island are chic shops and restaurants, beaches, and miles of quiet lanes and walking trails.

One of the most relaxing places in Massachusetts is laid-back Martha's Vineyard , only five miles from Cape Cod, but light years away in atmosphere. Its gentle landscapes are covered in farms and six villages, each with its own year-round local life. Some of its miles of beaches are beneath scenic sand bluffs. The appealing town of Oak Bluffs preserves rows of little 19th-century "gingerbread" cottages, built when it was a Methodist Camp meeting site; don't miss the historic merry-go-round, the Flying Horses Carousel .

  • Read More: Top Attractions & Things to Do in Nantucket

Salem and Cape Ann

North of Boston, and less visited than Cape Cod, Cape Ann is known for the picturesque fishing harbor at Rockport , and the working port of Gloucester. But in-the-know travelers come here for its beautiful and uncrowded beaches, its thriving art colonies, and the idyllic little towns of antique-filled historic homes .

Salem was the hub of the China Trade, and once one of the major ports on the East Coast, and its streets today are still lined by stately homes built for sea captains and prosperous merchants. It has literary connections as the birthplace and home of Nathaniel Hawthorne, and the added historic appeal of the infamous Salem Witch Trials -a grim history that Salem has turned into several tourist attractions.

  • Read More: Top-Rated Tourist Attractions in Salem and Cape Ann

Concord

Although Concord was of major importance in the struggle for independence - it was here that the "shot heard 'round the world" was fired at North Bridge on April 19, 1775 - it is as well-known for the transcendentalists . This remarkable group of writers and philosophers who lived and worked here included writers Ralph Waldo Emerson, Louisa May Alcott, and Henry David Thoreau, and they created some of their most famous works here.

You can visit the Alcott's Orchard House , preserved in its original state, where Louisa set her semi-autobiographical novel Little Women . Walden Pond , immortalized in Henry David Thoreau's writings, is part of a 411-acre nature preserve with a replica of his cabin.

For an overview of Concord's Revolutionary history and literary legacy visit the excellent Concord Museum , where you'll find Native American artifacts, Thoreau's snowshoes and furniture, Ralph Waldo Emerson's study, and the original lantern that signaled Paul Revere, along with collections of 17th- to 19th-century decorative arts and furniture.

Lexington

Northwest of Boston is Lexington, where the first shots in the War of Independence took place on April 19, 1775. A Minuteman statue by sculptor Henry Hudson Kitson and a monument mark Battle Green, where colonial militia members (called the Minutemen for their ability to get ready for battle in a minute's notice) clashed with British troops.

Minutemen and their commander, Captain Parker, gathered in the 1710 Buckman Tavern before confronting the British, and its interior, preserved as it would have been in the 18th century, is complete with the original seven-foot-wide taproom fireplace. The old front door still contains British musket-ball holes.

Munroe Tavern , built in the early 1690s, became a field hospital for the wounded and contains period artifacts and furniture. The Hancock-Clarke House contains period furniture of the Clarke family and Reverend John Hancock, grandfather of the signer of the Declaration of Independence.

Plimoth Patuxet Museums

Pilgrims fleeing religious persecution in Britain arrived in Plymouth in 1620 on board the Mayflower , establishing the first permanent European settlement in the north. Plymouth Rock marks the place where the Pilgrims first landed.

Visit a re-creation of their village, peopled by costumed interpreters who play roles of actual Pilgrims at Plimoth Patuxet Museums (formerly known as Plimoth Plantation ), and learn about the life of Native Americans who welcomed them at Hobbamock's Homesite.

Pilgrim Hall Museum opened in 1824 to showcase Pilgrim artifacts; furniture; decorative arts; painting; and the remains of the Sparrow Hawk, a wooden ship that wrecked off Cape Cod in 1626. Highlights include Governor Bradford's bible, Myles Standish's sword, and the original cradle used by Peregrine White, who was born on the Mayflower. Sparrow House , built in 1640 and Plymouth's oldest surviving wooden house, shows how primitively the first settlers lived.

  • Read More: Top-Rated Attractions & Things to Do in Plymouth, MA

The Southern Berkshires

The Berkshires, with their green hills, white churches, photogenic villages, and narrow country lanes, present the idyllic view of New England. Since the early 1800s, the southern communities of this region, which covers the entire area of western Massachusetts, have been a magnet for creative talent, and this cultural largess of music, dance, art, and literature is one of the region's major tourist attractions .

So are the miles of hiking trails, scenic waterfalls, and the ski areas of Butternut and Catamount , which combine to make the southern Berkshires one of the favorite places to visit in Massachusetts in the winter. Among the natural highlights are 80-foot Bish Bash Falls and the hike to the summit of Monument Mountain .

Stockbridge was home to the artist Norman Rockwell, and the Norman Rockwell Museum features his original works. Chesterwood was the summer home of Daniel Chester French, sculptor of the Seated Lincoln in Washington's Lincoln Memorial; his studio showcases his work, including working models.

In Pittsfield , you can tour Arrowhead , home of Moby Dick author Herman Melville . Lenox , best known for Tanglewood , the summer venue of the Boston Symphony Orchestra, was home to Pulitzer Prize winning author Edith Wharton, who built The Mount here in 1902 on a 40-acre estate, where you can tour her extraordinary Italianate gardens.

If you love gardens, be sure to also see the Berkshire Botanical Garden in Stockbridge. The Berkshire Museum in Pittsfield features works by American artists, an Egyptian mummy, and antiquities from Classical Greece and Rome. Naumkeag is the 44-room summer residence of a prosperous family, filled with antiques, art, and Chinese porcelain.

Mohawk Trail and the Northern Berkshires

Tony Award-winning Williamstown Theater Festival and the many resources of Williams College make Williamstown a cultural hub in Western Massachusetts. The Clark Art Institute Museum features extensive collections of European and American painting and sculpture, highlights of which are the works of French Impressionists and American painters Winslow Homer and John Singer Sargent.

Hike the Maine-to-Georgia Appalachian Trail as it crosses the summit of Mt. Greylock , the state's highest point, or you can drive to the top for views of three states.

Williamstown is the start of the scenic driving route, the Mohawk Trail , which follows an old Native American trail across western Massachusetts. In North Adams, MASS MoCA is an arts center for sculpture, theater, dance, and film, housed in 27 restored historic buildings. Hancock Shaker Village features a working farm using Shaker methods and 20 original furnished buildings used by the Shaker community from 1783 to 1960, including the Round Stone Barn.

Sawmill at Old Sturbridge Village

Worcester is an industrial city west of Boston, at the center of rolling rural countryside. Its prosperous history shows in the collections of the Worcester Art Museum , whose more than 35,000 pieces are highlighted by European and American works, Asian art, Greek and Roman sculpture, and contemporary art.

The most recent addition is the outstanding collections of medieval, Japanese, and other armor and artifacts from the now-closed Higgins Armory Museum . The indoor/outdoor EcoTarium complex features wildlife exhibits, a planetarium, and a tree-top walkway where you can learn about the New England environments and ecosystems.

Worcester was the major center of manufacturing diners between 1906 and the 1960s, turning out more than 600 of them that were transported across the country. You can honor this legacy by stopping at the well-preserved Miss Worcester Diner or Boulevard Diner .

Not far from Worcester is Old Sturbridge Village, a living history museum of more than 40 historic homes, farm buildings, and shops demonstrating New England crafts and daily life of the early 1800s. One of the state's most visited tourist attractions, Old Sturbridge Village appeals to all ages with its costumed interpreters demonstrating period crafts such as spinning, weaving, wool dyeing, pottery, tinwork, and blacksmithing, along with the daily tasks of farmers, millers, and homemakers.

In May, July, and September, the small town of Brimfield becomes the entire Northeast's Antiques Central, as dealers and collectors converge for several days of frenzied buying and selling at the Brimfield Antique Show and Flea Market .

New Bedford and Fall River

South of Boston and Cape Cod, New Bedford was the heart of the world's whaling industry in the 19th century, with 80 percent of the nation's whale ships, and factories turning whale oil into candles and whale bone into corset frames and umbrellas. This legacy is remembered in the excellent Whaling Museum , with displays on the history of whaling, a large scrimshaw collection, a whaleboat, whale skeletons, and a whaling film.

Also worth seeing are the Seamen's Bethel featured in Herman Melville's Moby Dick , and the 1834 Rotch-Jones-Duff House with decorative arts, antique furniture, and extensive gardens. Take a self-guided walking tour of the waterfront, preserved as the New Bedford Whaling National Historical Park , and still an active and colorful fishing port .

Nearby Fall River also has a rich history, both as a textile center and a shipping port, but perhaps its most famous citizen was Lizzie Borden, whose trial for her alleged murder of her parents still fascinates visitors to the Fall River Historical Society museum. The Marine Museum houses one of the world's largest Titanic exhibitions and models of the Fall River Line, a fleet of steamships that carried wealthy passengers from New York and Boston to summer homes in Newport.

At Battleship Cove, you can tour New England's largest floating museum, which includes the battleship USS Massachusetts , PT torpedo boats 796 and 617, the USS Lionfish , a WWII submarine, and the USS Destroyer Joseph P Kennedy , which served in Korea, Vietnam, and the Cuban Missile Crisis.

Historic Deerfield House

Near the Connecticut River in central Massachusetts, Amherst is home to the University of Massachusetts, Amherst College, and Hampshire College, making it a center for arts and culture with museums, galleries, bookstores, and performance venues. The Emily Dickinson Museum includes the poet's home and that of her brother, where you'll find collections and exhibits relating to her life and writing.

In nearby Hadley, a stage coach, oxcart, wagon, broom-making equipment, and other old farming equipment is shown in a restored 1782 barn at the Hadley Farm Museum . Several historic homes and a museum at Historic Deerfield illustrate the colonial and Federal periods in the Pioneer Valley.

Lowell

The Merrimack River powered some of the world's largest mills during the heyday of the textile industry, and in the Lowell area are a number of reminders of that era. The Middlesex Canal , built between 1793 and 1803, connected the Merrimack with the port of Boston, playing an important role in the Industrial Revolution that is explored at the Middlesex Canal Museum in Billerica.

The American Textile History Museum traces textile production from the 18th century to the mid-1900s with exhibits of hand-powered tools, machinery, fabrics, and garments.

Another facet of textile history is shown at the New England Quilt Museum , where you can admire the intricate handiwork in contemporary, traditional, and antique quilts. For a break from textiles, see works of James Abbott McNeill Whistler and other American artists at his birthplace, the Whistler House Museum of Art .

The major tourist attractions relating to Lowell's part in the Industrial Revolution are found at two open-air museums: the Lowell National Historic Park and the Lowell Heritage State Park . After seeing the videos, hop on the trolley for a tour, or in summer ride a boat along the canal system.

A guided tour of the Boott Cotton Mills Museum shows the weaving room where 88 looms pound away, powered by an ingenious system of shafts, belts, and pulleys all driven by the Merrimack River. Nearby, the former workers' boardinghouse concentrates on the living conditions and explores the stories of textile workers, often farm girls or immigrants. Lowell's textile mills were instrumental in the beginning of the American labor rights movement.

Newburyport Superior Courthouse

Newburyport has a rich history as an important seaport and shipbuilding center, and you can explore its seagoing past in the Custom House Maritime Museum . Get a look at the prosperity that shipbuilding brought to the city at the federal-style Cushing House Museum and its beautiful gardens. The house is filled with collections of furniture, silver, needlework and treasures brought back from exotic ports. The harbor is still active, and you can take whale-watching tours from its docks or enjoy a meal at one of the waterfront restaurants.

Nearby Plum Island is an 11-mile barrier island, with miles of beaches, dunes, and marshes protected by the Parker River National Wildlife Refuge . You can kayak in its marshes, walk its beaches, and watch for sea and shore birds from its boardwalks. For information on its resident and migratory birds, stop at the Massachusetts Audubon Society's Joppa Flats Education Center.

More Related Articles on PlanetWare.com

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Where to Go in Massachusetts: For even more information on what to see and do, refer to our pages on the Top-Rated Tourist Attractions in Massachusetts . This will give you a complete overview of the major tourist sites around the state. When you are ready to fine tune your itinerary, these articles will lead you to the best beaches , hiking trails near Boston , and the best weekend getaways .

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Exploring Nearby States : New England is a compact region, so it's easy to see the attractions of New Hampshire and explore historic Portsmouth , only a short trip from Boston. Northern New Hampshire is home to the White Mountains, where you'll find some of New England's best hiking trails and mountains for skiing . On the coast to the south is Rhode Island , with the spectacular mansions of Newport .

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Massachusetts Travel Guide

Visiting in the Fall

The natural beauty that dazzles us on a crisp, blue-sky autumn afternoon is the very same beauty that enticed settlers to the area to homestead, to start farms, and build communities.

There is no better way to immerse oneself in the glorious autumn foliage of the Berkshires than a road trip. An afternoon spent traversing the scenic byways of the Berkshires, reveling in the bright displays of leafy color, can easily segue into apple picking or a shopping spree in one of our vibrant communities, where the past is valued and the future is embraced.

Awe-inspiring Color

In the Berkshires, there are several routes that are especially dramatic and well worth the trip. Start on the  Mohawk Trail  along Route 2 near  Clarksburg , a route that includes the famous Hairpin Turn and magnificent view of extraordinarily vibrant foliage. Drive through  Williamstown  (a quintessential New England college town, with historic brick buildings and classic white churches) and turn south on Route 7 for views of farms and orchards nestled along a picturesque valley. Cloud formations cast moving shadows on the soft hills that rise to the right and left of the road, and there are several places to pull over, stop the car, and drink in the quiet beauty.

Choose to motor south on Route 8, from  North Adams  to  Mount Greylock , at 3,491 feet, the highest peak in Massachusetts. From Lanesborough, take the winding road to the top of Greylock for a spectacular display of foliage, golden yellow to blazing orange to vivid scarlet.  Bascom Lodge  offers delicious family-style dining and comfortable lodging in the rustic structure at Greylock’s peak, and there are options for hikes (including a section of the Georgia-to-Maine  Appalachian Trail ) and walks as well through the end of October.

Continuing south and west, Route 41 winds through Richmond and  West Stockbridge , past open fields and pastures, wooded lots and family farms. Or choose Route 183 between  Lenox  and  Stockbridge , meandering between stately trees shading the road, and then coming around a bend to a spectacular view of the Stockbridge Bowl, also called Lake Mahkeenac.

Average Temperatures

  • September 65°F
  • October 54°F
  • November 44°F

Discover Our Heritage

A road trip through the Berkshires is an ideal opportunity to indulge a fascination with history, and a visit to  Mission House  in Stockbridge is an excellent place to begin. The circa 1742 home and garden interpret the days of Colonial Stockbridge when the site boasted both English and Mohican residents.

Traveling south through  Great Barrington  and then towards Sheffield, there are many notable destinations for history buffs including the  Ashley House  a house museum dating to the eighteenth century, where visitors can learn the inspiring story of Elizabeth Freeman, a slave who sued for and won, her freedom in 1781. On the Sheffield-Egremont Road, just at the border between the two towns, stand the modest monument to the last Battle of Shays’ Rebellion, on February 27, 1787.

Bring the Berkshires Home

Browse at one of the several fine independent booksellers in the county, or delight in the shelves of enticing playthings at one of the area’s independent toy shops. For the dedicated antique collectors, there are many fine dealers, with clusters of shops in Sheffield, Great Barrington, Lenox,  Lee ,  Pittsfield , and Williamstown. Savvy collectors will find exquisite china and crystal, either a single perfect piece of an array of gleaming place settings; handcrafted weathervanes with a whimsical air, rescued from New England barns; or beautifully build Shaker furniture, still to be found in the region where it was originally crafted. Discover a first-edition of a great American novel or an elegant Queen Anne highboy while engaged in a fascinating conversation with one of the many knowledgeable dealers in the Berkshires.

  • Fall Family Activities
  • Annual North Berkshire Fall Foliage Parade
  • Apple Squeeze in Downtown Lenox
  • Founder’s Weekend in Downtown Lee

massachusetts towns to visit in fall

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10 Charming Small Towns to Visit in Massachusetts

From the coast to the hills, these are the best small towns to visit in Massachusetts.

massachusetts towns to visit in fall

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Massachusetts is home to nearly seven million residents sprinkled across 10,565 square miles, but not everyone lives in its bustling metropolises like Boston, Worcester, and Springfield. The state is punctuated by hundreds of smaller towns that are worth exploring, from charming coastal villages to historic mountain towns.

“With 351 cities and towns across the Commonwealth, the small towns of Massachusetts are bursting with history, culture, innovation, cuisine, and natural beauty,” Maria Speridakos, the director of international public relations at the Massachusetts Office of Travel and Tourism, shared with Travel + Leisure . “Visitors love to explore our seaside towns and fishing villages along the coast, from north of Boston down to the Cape and Islands and southeastern Massachusetts. And they love our charming small towns nestled in the rural byways and mountains of Central and Western Massachusetts, and the historic towns in the Merrimack Valley and Pioneer Valley.”

And, as Speridakos added, these places make for spectacular getaways no matter the time of year. 

“Massachusetts small towns are in vogue all four seasons, from spring getaways and summer vacations to fall foliage and winter outdoor adventures, ” Speridakos said. 

Want to get to know the state’s quaint communities a little better? Here are 10 small towns in Massachusetts worthy of planning an entire trip around.  

Related: 20 Best Weekend Getaways in New England

Provincetown

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Located at the very tip of Cape Cod , Provincetown has long been a summertime hot spot for Massachusetts residents and out-of-state tourists alike. And though it’s a rather famous spot, it’s still a small town, with fewer than 3,000 people calling it home year round. Come enjoy its beaches, its beloved Pride events, and its arts and culture scene, including its numerous galleries that are fantastic in summer, fall, winter, and spring.

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Located just 20 miles outside of Boston, Concord is one of the state’s most accessible small towns. The community is best known for its divine outdoor spaces like Walden Pond, which inspired some great American writers, including Henry David Thoreau and Ralph Waldo Emerson, who both called Concord home. 

Northampton

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Northampton is perhaps the “largest” of the small towns on the list with some 29,000 residents, but that doesn’t make it any less charming. Located in the western half of the state, this town has a rich arts scene (visit the Northampton Museum and Art Gallery ), local shops, and several music venues offering live performances.

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Back on the east coast of Massachusetts, travelers can explore Rockport , an adorable town of fewer than 8,000 residents at the tip of Essex County. The town offers year-round dining and shopping options, as well as plentiful beach and woodland hikes for those looking to get out and explore Mother Nature.

Williamstown

Tucked in the northernmost corner of the state, travelers will find the adorable community of Williamstown. It’s another small but mighty presence in the art world thanks to the Clark Art Institute, which showcases impressionist and contemporary artworks throughout the year. The town may also be familiar to hikers, as it’s located directly on the Appalachian Trail .

Barry Winiker/Getty Images

Make your way out to the Cape to visit Sandwich, the oldest community on the peninsula. With age comes both beauty and history; guests can visit historical landmarks like the Hoxie House Museum, a home built around 1675 that is likely the oldest saltbox home on Cape Cod. The Heritage Museums and Gardens and the famed Sandwich Glass Museum are also worth visiting.

Stockbridge

Have a picture-perfect getaway in Stockbridge . This teeny town in the Berkshires is so gorgeous, it inspired the great American painter and resident, Norman Rockwell. Come here to explore the lush natural landscapes or the more curated flora at the Berkshire Botanical Garden, and don’t miss the chance to see a show put on by the Berkshire Theatre Group.

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Put your toes in the sand when you visit Oak Bluffs, a quaint little town on the island of Martha’s Vineyard. The community is perhaps best known for Joseph Sylvia State Beach, a two-mile-long beach made famous in “Jaws.” The community also happens to be an A-list haven, counting the Obamas as summertime regulars.

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Take one more island escape by visiting Nantucket, an isolated island past Martha’s Vineyard. Home to a little over 11,000 full-time residents, the island is certainly small, but it too packs a wallop when it comes to history. Specifically, visitors here can check out three historic lighthouses: Great Point, Sankaty Head, and Brant Point . Travelers will also be delighted by the bountiful seafood spots to enjoy here, as well as some rather excellent boutique shopping. 

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Did you know you can ski in Massachusetts? Just head to the town of Westford to see for yourself. Located in the northern part of the state close to the New Hampshire border, visitors can hit the slopes at the Nashoba Valley Ski Area . Of course, it’s a year-round destination, thanks to its hiking and biking trails and sights like The Butterfly Place , an indoor living environment for butterflies from all over the globe.

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massachusetts towns to visit in fall

8 Best Places To Visit In Massachusetts In The Fall Season 2023

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Starting in early October is the best time each year to take a road trip and enjoy the legendary fall colors in Massachusetts. The fall colors tend to move from west to east each year.

The leaves start to change in the Berkshires around the first week in October, in central Massachusetts by the second week, and along the coast for the last two weeks. Times may vary, but these will generally give you the best chance to see the dazzling colors.

Here are 8 great places to check out the fall colors in Massachusetts.

The Mohawk Trail

massachusetts towns to visit in fall

The Mohawk Trail is a 60-mile road that stretches between Williamstown and Greenfield. The views on this scenic drive are unparalleled in the rest of Massachusetts, and it makes for a stunning road trip in October.

There’s also no shortage of activities along the route, including stopping to visit breweries, cideries and numerous scenic overlooks. Don’t forget to check out “The Elk on the Trail” statue at Whitcomb’s Summit.

Berkshire County

Berkshire Fall Season

Berkshire County is a beautiful place to see the fall colors on the western side of the state. “The Berkshires,” as the area and the rolling mountains are called, have many scenic drives and hikes you can take to soak in the views.

The Berkshires are well known as a spot for a cozy or romantic getaway. There is a wide selection of bed and breakfasts, cabins, and quaint inns to choose from.

Quabbin Reservoir

massachusetts towns to visit in fall

Quabbin Reservoir is centrally located in Massachusetts, so it’s very accessible from other locations around the state. It is the largest body of water in inland Massachusetts, so it’s hard to miss.

The reservoir has more than 100 miles of hiking trails through the wooded hills surrounding it. There are also scenic overlooks that are perfect for enjoying the fall colors.

Concord in Fall Season

Concord is an iconic Massachusetts city known for its connections to the American Revolutionary War. It’s also the home of Walden’s Pond and Louisa May Alcott. The city is perfect for a fall getaway or road trip.

One of the best places to check out the fall colors is along the Battle Trail at the Minute Man National Historical Park, which is just east of the city. Walden’s Pond is another must-see location surrounded by trees and beautiful views.

Mount Greylock Summit

Mount Greylock Summit in the Fall

The Mount Greylock Summit in the Berkshires is the highest point of elevation in Massachusetts. Visitors can either hike or drive to the top.

On a clear day, you can see up to 90 miles in the distance. The town of Adams is at the base of the mountain, and there are various inns and campgrounds to stay in nearby.

The Bridge of Flowers

massachusetts towns to visit in fall

The Bridge of Flowers is one of the best-known attractions in the little town of Shelburne Falls, MA. The Bridge of Flowers is a footbridge that spans the Deerfield River in the downtown area of Shelburne Falls.

The footbridge has a gravel path running through the middle of it, and a row of beautiful flowers and plants on each side of the path. It’s obviously a very pretty walk during the summer months when the flowers are in full bloom.

However, there are still a few plants blooming in the fall when the leaves start to change. If you look to the west as you’re crossing the Bridge of Flowers, you can see the fall foliage on the hillside above town.

Newburyport

Newburyport

Located on the coast north of Boston, Newburyport is a pretty town with some great places to catch the fall colors. It has several scenic waterfront parks along the Merrimack River where you can catch the leaves turning.

Maudslay State Park, Mosely Woods, and City Forest are three other areas within the town limits with plenty of trees. Newburyport also has some fun community events in the fall, including an Oyster Fest. 

Amherst Fall Season

Amherst is located to the west of the Quabbin Reservoir, mentioned above. The little city is famous for being the home of poet Emily Dickinson, and there is a museum dedicated to her in the town. It’s also home to Amherst University.

The town has several rail trails and hiking trails that are fun to explore during the fall. The Norwottuck Rail Trail is 11 miles long and offers tree-lined views most of the way. 

Correction, Amherst Mass is the home of the University of Massachusetts-Amherst, which is pictured, as well as Amherst College. Two distinctly different schools. (There is no school called Amherst University) Amherst, and surrounding towns are beautiful in the fall.

I was under the impression Bridge of Flowers was under renovation this year.

Concord, Massachusetts is a town, not a city.

Very beautiful pictures. Thank you,so much.

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massachusetts towns to visit in fall

10 Things To Do In Pioneer Valley: Complete Guide To This Scenic, Small Massachusetts Town

W hen most people think about Massachusetts, their minds naturally gravitate towards Boston, the bustling state capital . But away from the big city, approximately two hours to the west lies an overlooked New England gem. Pioneer Valley is a small yet scenic region ranked among the most underrated destinations in the US by CNN Travel. It is a testament to the natural beauty, vibrant arts scene, rich history, and delightful adventures that define it.

A nature lover’s dream come true, the valley straddles three counties, Franklin, Hampden, and Hampshire, surrounded by rolling hills, lush forests, and meandering rivers offering unique outdoor excursions. Pioneer Valley hosts a lively student population from a five-college consortium, including the University of Massachusetts Amherst and Smith College. Its eclectic mix of theaters, galleries, and music venues guarantees a bustling arts and culture scene, offering some of the best things to do in Massachusetts .

However, that is only the tip of the iceberg, and first-timers will have a remarkable experience uncovering the diverse attractions in this West Mass destination.

Related: 10 Free Things To Do This Fall In Massachusetts

Things To Do In Pioneer Valley

Whether an outdoor enthusiast, cultural connoisseur, history buff, or foodie, Pioneer Valley is the gift that keeps on giving, offering something to excite all types of travelers. Here are the top things to do in these must-visit small Massachusetts towns .

Visit The Naismith Memorial Basketball Hall Of Fame

The popular game of basketball was invented in 1891 by James Naismith, a Canadian physical education coach. He wanted to create a fast team sport while working at the International YMCA Training School in Springfield and ended up nailing two wooden baskets on opposite walls; thus, the beautiful game was born.

At the Naismith Memorial Basketball Hall of Fame, fans can learn exciting history about the game and celebrate some big-name players and coaches who have earned it global acclaim.

Visitors also inspect various interactive exhibits, a game gallery, and shoot hoops at the Center Court.

  • Admission : Adults $29, Seniors $25, Youth $20, Student $25
  • Hours : 10 am – 4 pm, daily

Coin collectors looking to add to their haul can pick up unique e-coins in the lobby.

Stop By The Amazing World Of Dr. Seuss Museum

Tourists can reminisce about their childhood at the Amazing World of Dr. Seuss Museum, Springfield. This remarkable museum pays homage to the life’s work of Theodore Geisel (Dr. Seuss), a Springfield native and renowned children’s book author. It hosts a collection of interactive exhibits that allow guests to learn about some of his iconic characters, including Cat in the Hat, Horton, and Dr. Seuss.

They can also admire the galleries on the upper floors displaying original artworks and several letters Theodor Geisel wrote to his nephew. Kids will love the storytelling and rhyming games staff hold on the first floor.

  • Admission : Adults $25, Seniors & College Students $16.50, Youth $13, Children Under 3: Free
  • Hours : Tue to Sat (10 am – 5 pm), Sun (11 am – 5 pm)

The Amazing World of Dr. Seuss Museum is part of the Springfield Museums , and the ticket grants visitors access to four other museums in downtown Springfield and the Dr. Seuss National Memorial Sculpture Garden.

Step Back In Time At The Historic Deerfield Village

History buffs can travel back to the medieval ages by strolling through the main street of Historic Deerfield Village. Stuck in time, this fossil of a village comprises about a dozen house museums dating back to the 18th and 19th centuries, allowing tourists a rare glimpse into hundreds of years of history.

The houses are well-preserved and retain the ancient furniture used by their original inhabitants. Elsewhere, a museum hosting several artifacts and active workshops exposes travelers to old-fashioned woodworking, cooking, and farming techniques.

  • Admission : Adults $18, Youth $5
  • Hours : Wed to Sun, 9:30 am – 4:30 pm

Don’t forget to walk along the 330-year-old street at Historic Deerfield Village and visit the Old Burying Ground , the final resting place of some of the original settlers.

Related: 10 Historic Homes In Boston You Need To See

Read A Book At The Eric Carle Museum Of Picture Book Art

The Eric Carle Museum of Picture Book Art celebrates the life and work of Eric Carle, cofounder of the venue and author of the popular picture book The Very Hungry Caterpillar . It hosts three galleries with rotating exhibits dedicated to book illustrations from all over the world and a permanent exhibition that visitors can inspect and admire.

The most extensive gallery celebrates Carle’s prints, whereas the other two showcase works by other famous kids’ books illustrators like Louis Darling, illustrator of several of Beverly Cleary’s early books. There’s also a gift shop at the museum with cute merchandise and children’s books visitors can buy.

  • Admission : Free
  • Hours : Wen to Fri (10 am 4 pm), Sat (10 am – 5 pm), Sun (12 – 5 pm)

The Eric Carle Museum of Picture Book Art is perfect for inspiring older kids and teens who have shown an interest in illustration.

Explore The Outdoors At Skinner State Park

Home to multiple hiking trails and incredible vistas of the Connecticut River Valley, the Skinner State Park offers outdoor lovers an excellent opportunity to break a sweat while exploring the lush open spaces in Pioneer Valley.

Its proximity to the Holyoke Range enables explorers to discover Horse Caves and ledges along the New England Scenic Trail, where fighters would hide during the 1897 Shays’ Rebellion.

A hike to the top of Mt. Holyoke, which rises to 942 feet, rewards adventurers with sweeping views of the Connecticut River and its green river valley. Hikers can access the 1.5-mile path to the summit around the year, but vehicles can only drive on it between May and October.

Remember to pop into the Summit House at the mountain's peak, a former 1861 hotel turned visitor center. It has old photos of the venue during its heydays from the early 1900s.

Get An Adrenaline Boost At Six Flags New England

Thrill seekers yearning for an adrenaline injection will find the perfect remedy at Six Flags New England, which sits adjacent to the scenic Connecticut River. With a history dating back to the 1800s, it is the oldest theme park in the franchise and the largest amusement park in New England, comprising over 60 fun rides with 13 roller coasters and a water park.

The Skyscreamer was the world’s tallest swing ride when it debuted in 2014 and promises a blood-cuddling experience even for the most hard-core adrenaline junkies. The same is true for Goliath, the venue’s super coaster, which reaches speeds of 65 mph with a 90-degree climb to 200 feet in the air.

  • Admission : Start at $42, depending on the package
  • Hours : Sat & Su, 11 am – 7 pm

Kids will relish meeting popular cartoon characters at the Looney Tunes Talent Show, where Duffy Duck, Bugs Bunny, and others square off in an American Idol-style competition.

Get Cultured At The Smith College Museum Of Art

Culture connoisseurs visiting Pioneer Valley will feel at home scoping out the over-27,000-piece collection at this magnificent facility. The Smith College Museum of Art displays gorgeous paintings, focusing more on 19th and 20th centuries North American and European artists, such as Picasso, Winslow Homer, Degas, and James Abbott McNeill.

Established in the 1870s, this leading academic institution inspires budding creatives with an artistic environment and special programs to instill artistic knowledge.

  • Hours : Tue to Sun, 11 am – 4 pm

Check Out The Springfield Armory National Historic Site

War historians and weaponry enthusiasts can stop at this fascinating National Historic Site in Springfield, which preserves the greatest federal armory in the country. The arsenal was constructed during the American Revolution following an order by George Washington and houses multiple old-day weapons.

Today, visitors can inspect one of the largest firearm collections in the world, featuring Colts, Remingtons, and Lugers. Some of these weapons were made as early as the 15th century, offering a vivid snapshot into the evolution of guns.

  • Hours : Wed to Sun, 9:30 am – 4 pm

For a deeper dive into the history of the exhibits, book a group tour with a knowledgeable guide tailored to visitor interests.

Related: Guide To New England's Most Important Revolutionary War Sites

Catch A Live Show At The Academy Of Music Theater

Established in 1891, the Academy of Music Theater is a historic 1000-capacity music venue in Northampton that rose to prominence as a go-to stop for leading performers throughout the 20th century. It has hosted big names like magician Harry Houdini, movie star Mae West, and the iconic French actress Sarah Bernhardt.

The venue continues to entertain locals and visitors by staging exciting live theater productions, dance shows, films, and music performances by local and international artists. It is also home to companies like the Pioneer Valley Symphony Orchestra, Pioneer Valley Ballet, Signature Sounds, and Valley Light Opera.

  • Admission : Depends on the show
  • Hours : Mon (9 am – 5 pm), Tue - Fri (3 pm – 6 pm).

Visit the Academy’s official website for scheduled performances, time, and ticket prices.

Discover Prehistoric Fossils At Dinosaur Footprints

A long time ago, during the Mesozoic period (about 190 million years), when the Pioneer Valley was still a subtropical swamp, bipedal dinosaurs roamed the area, and the cluster of giant footprints along the west bank of the Connecticut River offer evidence of this bygone era.

Although elements have eroded the sandstone holding the tracks through the years, a keen eye can pick out more than 100 prints representing three distinct dinosaur species. The site is a short walk off Route 5 in Holyoke and is a remarkable sight to explore.

Take extra caution when examining the tracks near the river; the rocks can be very slippery, especially when wet, and the river is pretty swift.

Best Time To Visit Pioneer Valley

Massachusetts is among the best New England states to visit in the fall , and the Pioneer Valley region delights tourists with its fantastic flurry of fall colors. Opportunities to step out and explore the town abound, with some kayaking and rafting along the river as others walk or drive along the Mohawk Trail to admire the kaleidoscopic foliage.

Spring is also a great time in Pioneer Valley as the weather shakes off the frigid winter chill. The 50s degrees Fahrenheit temperatures are a welcome reprieve for tourists and present an opportunity to leave their winter cocoons. However, the season is still wet, and the rain tends to interrupt outdoor expeditions.

Summer allows expeditioners to remain outside for all the adventures available in the Pioneer Valley. From touring the different museums and hiking its scenic trails to attending multiple festivals, this busy time in the region guaranteed to impress all types of travelers.

Winter is the worst time for visitors to the Pioneer Valley, as the freezing temperatures will confine them inside most of the time. However, those who can brave the cold can enjoy fun winter activities like cross-country skiing at Mount Holyoke Golf Course and shopping at the Amherst Winter Market.

Related: This Small Massachusetts Town Might Be The Cutest Winter Spot Yet

How To Get Around Pioneer Valley

Travelers in the Pioneer Valley region have multiple options to get around while exploring its diverse attractions. Depending on their preferences, here are the different modes of transportation to choose from:

The Pioneer Valley Transit Authority operates a fleet of buses ferrying passengers to various destinations throughout Springfield, Amherst, Northampton, and the surrounding areas. Each route is identifiable by an electronic sign displayed on the front, rear, and side of the bus.

  • Fares : $1.50 for adults, $0.75 for seniors, $15 for a 7-day pass

Peter Pan Bus Lines is an alternative public transit system with a broad network of long and short-distance routes from its hub at Springfield Union Station. These have stations in Greenfield, Deerfield, Springfield, Amherst, Northampton, etc.

The Pioneer Valley Region is served by a handful of train services, including Amtrak, which has Springfield, Amherst, and Pittsfield stations, and the Valley Flyer passenger rail service, which connects with Amtrak’s Northeast Corridor service.

Tourists can also access various car rental agencies, including Enterprise and Avis, across the major towns in the region for a customized itinerary when moving around the Pioneer Valley. This will also be useful for explorers looking to embark on a multi-day road trip to explore Massachusetts .

Where To Stay In Pioneer Valley

Pioneer Valley covers about half a dozen small towns that are among the best places to visit in New England , each with a unique personality and exciting points of interest to offer visitors a fresh experience wherever they choose to stay. This means there are enough lodging options to cater to different preferences and budget needs.

Here are the best places to stay in the Pioneer Valley.

Springfield

Springfield is the cultural and economic capital of West Mass and home to a treasure trove of New England historical gems . Highlights include the Naismith Memorial Hall of Fame and the Springfield Armory National Historic Site. It also hosts three universities with a vibrant young population and diverse entertainment options. Top hotels here include:

Marriott Springfield Downtown

  • Address : 2 Boland Way, Springfield, MA 01115
  • Rates per night: Start at $213
  • Amenities : Indoor pool, Fitness center, Restaurant, Bar/Lounge, Room service, Free Wi-Fi, Tea/coffee maker, Coffee machine, Wi-Fi available in all areas, Flat-screen TV

Naomi's Inn Bed & Breakfast

  • Address : 20 Springfield Street, Springfield, MA 01107
  • Rates per night: Start at $141
  • Amenities : Pool, Free Wi-Fi, Private bathroom, Complimentary breakfast, Coffee machine, Terrace/Patio, Balcony, Air-conditioned, Flat-screen TV

Amherst is a renowned college town housing revered academic institutions like the University of Massachusetts, Hampshire College, and Amherst College. It offers an eclectic mix of educational and cultural opportunities, among its highlights being the Emily Dickinson Museum. Top-rated hotels include:

Courtyard by Marriott Hadley Amherst

  • Address : 423 Russell Street, Hadley, MA 01035
  • Rates per night: Start at $215
  • Amenities : Indoor pool, Fitness center, Restaurant, Bar/Lounge, Free Wi-Fi, Coffee machine, Coffee shop, Free parking, Business center, Flat-screen TV

Howard Johnson by Wyndham Amherst Hadley

  • Address : 401 Russell Street, Amherst, MA 01035
  • Rates per night: Start at $127
  • Amenities : Fitness center, Free Wi-Fi, Tea/coffee maker, Coffee machine, Business center, Wi-Fi available in all areas, Cable or satellite TV, Free toiletries, Meeting/Banquet facilities

This quaint little town near the Connecticut River, with a rich tourism heritage, is one of the most charming places to live in New England . It is home to the Yankee Candle Company and the Historic Deerfield Village, which harbors interesting historical gems. Lodging options here include:

Red Roof Inn Plus+ South Deerfield - Amherst

  • Address : 9 Greenfield Road, South Deerfield, MA 01373
  • Rates per night: Start at $133
  • Amenities : Indoor pool, Free Wi-Fi, Tea/coffee maker, Free parking, Wi-Fi available in all areas, Flat-screen TV, Cable or satellite TV, Free toiletries, Pets allowed on request. Charges may apply, Laundry facilities

Deerfield Inn

  • Address : 81 Old Main Street, Deerfield, MA 01342
  • Rates per night: $
  • Amenities : Free Wi-Fi, Air-conditioned, Laundry facilities, Room service, Babysitting or child care, Gift shop, Bicycle rental, Elevator, Hiking, Storage available

Where To Eat In Pioneer Valley

Newcomers in the Pioneer Valley can look forward to a delectable dining experience, with restaurants serving a magical mix of flavors. The fertile river valley ensures a constant supply of fresh farm-to-table ingredients to prepare everything from classic New England dishes to international cuisines.

The region also boasts a lively craft brewery scene and vibrant nightlife, featuring multiple bars and pubs to entertain the youthful student population. Here are the best joints to eat in Pioneer Valley.

Breakfast :

  • Address : 282 Main St, Greenfield, MA 01301-3201
  • Hours : Tue to Sat, 7 am – 2 pm

Lunch & dinner:

Paul & Elizabeth’s

  • Address : 150 Main St, Northampton, MA 01060-3598
  • Hours : Mon to Sat, 12 – 7 pm

Ginger Garden

  • Address : 351 Northampton Rd, Amherst, MA 01002-2547
  • Hours : Sun to Thur (11 am – 10 pm), Fri & Sat (11 am – 11 pm)

The Dirty Truth

  • Address : 29 Main St, Northampton, MA 01060-3182
  • Hours : Tue (4 pm – 9 pm), Wed to Sat (12 pm – 9 pm)

Related: Boston, Massachusetts: Planning The Perfect Weekend

How To Spend The Perfect Day in Pioneer Valley

Start the day by exploring the Springfield Museums downtown for an immersive historical tour. Head to the Amazing World of Dr. Seuss Museum to learn about the iconic children’s book writer, then the Dr. Seuss Memorial Sculpture Garden to examine iconic life-sized characters from his various books.

Later, stop by the George Walter Vincent Smith Art Museum and admire the gorgeous artwork before exploring the region’s entrepreneurial spirit at the Lyman and Merrie Wood Museum of Springfield History. Finally, wrap up the Springfield Museum tour at the Springfield Science Museum.

Grab a quick lunch in one of the cafes in the area and proceed to the Naismith Memorial Basketball Hall of Fame to find out the modest beginnings of the beautiful game or honor its legends.

Take a trip to Northampton to check out the historic downtown of one of the oldest towns in New England. Afterward, hit the hiking trails at Skinner State Park and soak in the scenes atop Mt. Holyoke, then follow this up with a trip to Dinosaur Footprints to hunt for prehistoric fossils.

After the strenuous expedition, relax by watching a delightful live performance at the Academy of Music Theater until darkness sets in, and it’s time for a wholesome dinner at Paul & Elizabeth’s Diner. Lastly, cap off the day with cocktails at The Dirty Truth.

10 Things To Do In Pioneer Valley: Complete Guide To This Scenic, Small Massachusetts Town

10 Places To Visit In Massachusetts This Fall (That Do Not Include Salem)

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10 State Parks In Washington With Scenic Hikes

10 additional scenic stops to make if you're visiting the grand canyon, this city in new york was named the number one city in america, here's why.

Although Salem is often thought to be the quintessential Massachusetts destination for fall, the state has so much more to offer. From scenic mountain drives to historical sites to outdoor sporting events, the Bay State offers something for every traveler this autumn. Get lost in nature on hikes for every skill level, or go for an early morning sail to watch the sunrise set fire to the ruby and auburn hues of the trees along the shoreline. Massachusetts is an iconic fall destination not only because of its natural beauty but also because of the endless list of things to do and see all over the state this autumn. Check out these local finds and hidden gems in every corner of Massachusetts.

10 Explore American Literary History In Amherst

Amherst, a quaint town of about 40,000 people, is home to the birthplace and residence of 19th-century poet Emily Dickinson. The Emily Dickinson Museum is composed of two buildings, including Dickinson’s home and that of her brother. The author’s reclusive and secretive nature has left many questions about her life, but what answers remain can be found in her modest yellow home. Dickinson’s poetry reflects a rich and expansive inner world, but in reality, her grave is located less than half a mile from her childhood home. Literary travelers will enjoy an intimate glimpse into the life of a great American poet.

9 Visit An American Castle In Haverhill

Winnekenni Castle in Haverhill was erected in the 1870s by American agriculturalist and chemist James R. Nichols. Perched on a hill overlooking serene Lake Kenoza, Scottish and English stone architecture directly influenced the massive structure influenced by Scottish and English stone architecture . The park in which the castle is set offers activities year-round for the community and visitors. However, in autumn, the lush woods around the castle and the lake present truly majestic views from nearly every angle.

Related: For Charm And Architecture, Try Touring These Historic Neighborhoods

8 Discover Quabbin Reservoir In Central Massachusetts

The largest inland reservoir in Massachusetts , Quabbin Reservoir, offers outdoor activities, including fishing, boating, and walking. Located in Belchertown, the reservoir features 180 miles of lake coastline and sprawls over 39 square miles. Visiting at the height of the fall foliage season, travelers are engulfed in the dazzling hues of the trees and the cerulean blue of the reservoir. Travelers are welcome to bring a picnic to enjoy a meal in nature. Boat rentals are also available for those interested in exploring the lake and its islands.

7 Find Whales (Not Just Rocks) In Plymouth

While Plymouth is often associated with colonial history, the town has much more to offer the curious traveler . A little-known fact: Plymouth is a good location for whale watching from spring into fall. Visitors seeking adventurous nature experiences and historical tours can find the best of both here. Whale-watching tours can be taken all day, but sunset tours add special magic to the moment. The sunset on Plymouth harbor illuminates the coastal treeline. Ocean conditions change quickly, and whale pods can move great distances in a short time, so visitors hoping to spot whales should confirm with the boat operator close to the sailing date.

6 Learn About Historical Seaside Marblehead

Marblehead is a charming seaside town with a long history . The town was originally occupied by a community of Native Americans who were members of the Algonquin Nation. In 1684, the area became a British settlement. Centuries-old architecture still stands here, tucked among small-town mom-and-pop shops and romantic winding lanes. For a taste of historical Massachusetts, with a sprinkling of bright autumn leaves and a generous dash of charm, travelers should add Marblehead to their Massachusetts itinerary this fall.

Related: These Massachusetts Locations Inspired The Novels By Horror Legend H.P. Lovecraft

5 Sleep Aboard A Battleship In Fall River

Fall River holds a special place in the hearts of maritime and military enthusiasts. The city is home to Battleship Cove, a massive collection of World War II-era battleships. Visiting families can also enjoy an overnight camping experience aboard the USS Massachusetts . Visitors learn about the decommissioned battleship, once active in WWII battles in North African and South Pacific waters. Battleship Cove is an especially memorable experience for young travelers and a little-known highlight of any autumn visit to Massachusetts.

4 Take The Mohawk Trail Scenic Drive

A fall foliage drive is a simple, fuss-free way to enjoy the beauty of the Bay State in the fall. The Mohawk Trail offers a picturesque scenic drive roughly parallel to the Deerfield River. This long-established trail once served as a trading route dating back thousands of years. Today, great finds along this route include charming small towns, local eateries, and spellbinding overlooks.

3 Enjoy Rally And Regatta In Cambridge

There are few quintessentially Massachusetts moments as memorable as picnicking on the banks of the Charles River in Cambridge, Massachusetts. The Head of the Charles Regatta is a half-century-old rowing race that includes thousands of athletes in the annual competition. The race happens in the autumn, so it is the perfect time to enjoy beautiful fall foliage against the sparkling backdrop of the Charles. Visitors can access parts of the Harvard University and Massachusetts Institute of Technology (MIT) campuses from the river bank for an added attraction.

2 Relish Nantucket’s Other Peak Season

While most travelers tend to associate Nantucket with summer travels, there are plenty of reasons to visit in the fall . The summer crowds give way to an unhurried pace in the autumn. Visitors can enjoy delectable dining, sunsets over the Atlantic Ocean, and boutique shopping without feeling crowded or rushed. Travelers can arrange an early fall sail to see for themselves why Massachusetts is known as the Bay State. Bed and breakfast accommodations tend to have fewer bookings after the summer, so visitors have better odds of snagging a cozy room in one of the many Instagram-worthy B&Bs.

Related: Why Nantucket Is Often Called 'The Grey Lady,' And More Maritime History To Know Before Visiting

1 Take The High Road In Mount Greylock

The highest point in Massachusetts , Mount Greylock, offers mountain biking, hiking, camping, and a host of other outdoor activities. With an elevation of nearly 3,500 feet, Mount Greylock features hikes of many difficulty levels . Travelers should carefully choose their routes. The auto roads are open through the fall to allow visitors to drive through the area by car. What’s more, the area is pet friendly, so visitors can bring their four-legged friends (on a leash) to enjoy the fall splendor too.

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COMMENTS

  1. Fall In Massachusetts Ultimate Guide: 35 Things To Do & Places To Visit

    One of my favorite small towns in Massachusetts to visit in the fall season is Sturbridge. Honestly, Sturbridge is charming year-round, but winter, and especially fall, are simply magical here.. The biggest attraction in Sturbridge is Old Sturbridge Village, which is a recreation of a New England town in the 1830s, and spans over 200 acres.

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    Look at these gorgeous MA fall views! Located in Great Barrington, a town in the Berkshires that Vogue once described as "quietly cool," Monument Mountain offers scenic views from its 1,624-foot summit that allow you to look out across the Housatonic River Valley, with the Catskills of New York in the distance.. Monument Mountain has a storied place in literary history as well, as it is ...

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    To see the fall foliage in all its splendor on the south shore of The Bay State, head to Plymouth. Famous for being a landing site of the Mayflower Pilgrims in 1620, Plymouth is a historic town home to iconic places like Plymouth Rock. Visiting these towns painted in autumn colors makes the experience even more special.

  5. Prettiest Fall Foliage Villages in Massachusetts

    Mount Greylock | Prettiest Fall Foliage Villages in Massachusetts. Photo Credit : Photo by Doug Kerr / CC BY. Mount Greylock State Reservation. At 3,491 feet, the summit is the highest point in Massachusetts and a must-see foliage destination with eye-popping views of the Berkshires and beyond. The reservation offers 70 miles of designated ...

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    Newburyport, MA is a fun town for dining, shopping, browsing art galleries, and strolling. A brick plaza - in contrast to the traditional New England green - is the heart of the town, and lots of public events happen here. If you visit in the fall, you might easily stumble upon an Oktoberfest or a family fall festival.

  7. 10 Top Places To Visit In Massachusetts In The Fall

    Bash Bish Falls in Berkshires, Massachusetts, surrounded by fall foliage. There are many waterfalls in Massachusetts with breathtaking views of the changing leaves. However, Race Brook Falls in Sheffield, Campbell Falls in New Marlborough, and Bash Bish Falls in Mount Washington are the most gorgeous worth visiting in the fall.

  8. Massachusetts Fall Foliage Guide

    Best Massachusetts Fall Foliage Towns. 1. Williamstown. Located in the shadow of Massachusetts's highest mountain — Mount Greylock, in nearby Adams — Williamstown may be the ultimate college town: Its mix of eclectic architecture and inviting green spaces can't help but inspire lofty thoughts. While the drive up Mount Greylock affords ...

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    Plus, taking some of these haunted tours will definitely let you make the most of your time in one of the best towns to visit in the fall in Massachusetts. Salem Witch House and Museum If you'd rather strike out on your own, the two best places to start are at the Salem Witch House (310 1/2 Essex St) and the Salem Witch Museum (19 1/2 ...

  10. Massachusetts In The Fall: Most Beautiful Fall Day Trips To Take

    Here are some of the most beautiful places to visit in MA in the fall. 1. Old Sturbridge Village. Old Sturbridge Village, 1 Old Sturbridge Village Rd, Sturbridge, MA 01566, USA. Old Sturbridge Village/Facebook. Fall in Massachusetts may be the best time to visit Old Sturbridge Village, an open-air museum depicting 18th and 19th-century rural ...

  11. Mass. has one of the 15 best fall foliage trips, Fodor's Travel says

    A 90-mile drive rich with scenic views and historic sites along the Massachusetts coast is one of the best places in America to view fall foliage, according to Fodor's Travel. The publication ...

  12. 10 Best Places To Visit In Massachusetts In The Fall

    3. Forest Hills Cemetery, Boston. Cemetery Road, Cemetery Rd, Boston, MA 02130, USA. Flickr/Bill Ilott. You might not think a cemetery would be one of the best places to see fall foliage in Massachusetts, but Forest Hills Cemetery is one of a kind. This historic cemetery comes to life (though thankfully not literally) with a rainbow of colorful ...

  13. 12 Best Things to Do in Massachusetts in the Fall

    Celebrate all things marshmallow at What the Fluff. 2. Go back in time at King Richard's Faire. 3. Have fun at Massachusetts largest fair. 4. Experience thrills and chills at Six Flags New England's Fright Fest. 5. Celebrate Halloween in Salem, Massachusetts.

  14. Leaf Peeping: 10 Least-Crowded State Parks In Massachusetts To See Fall

    Here are some of the least-crowded towns in Massachusetts in the fall with peaceful state parks nearby that promise a haven for breathtaking fall foliage in this New England state. Related: 10 Things To Do In Boston: Complete Guide To The Capital Of Massachusetts. 10 Fort Phoenix State Reservation, Fairhaven

  15. 31 Fun Things To Do In Boston In The Fall (2024)

    One of my personal favorite fall places to visit that's close to Boston is Newburyport. This little city feels more like a quaint, small town, and has amazing shopping and dining, waterfront scenery, boat tours, and of course … fall foliage. ... MA; Fall Festivals & Events In Boston 27. Titanic Masquerade Halloween Yacht Party.

  16. The Best Fall Foliage Road Trip In Massachusetts

    Boston Public Garden is one of the best places for leaf peeping in Boston. Each and every September, Massachusetts proudly shows her colors. Burnt sienna, crimson red, and tawny yellow dance around swaths of evergreen, creating a palette that draws you in. The annual passing of summer and onset of autumn shine brightly in New England's foliage.

  17. 15 Best Places to Visit in Massachusetts

    Lowell. 15. Newburyport and Plum Island. Map of Places to Visit in Massachusetts. 1. Boston. Boston. From the Brahmin bastion of Beacon Hill and the historic sights of the famed Freedom Trail, to the world-class art museums, "The Hub" has something for everyone.

  18. Visiting in the Fall

    Or choose Route 183 between Lenox and Stockbridge, meandering between stately trees shading the road, and then coming around a bend to a spectacular view of the Stockbridge Bowl, also called Lake Mahkeenac. September 65°F. October 54°F. November 44°F. Visiting the Berkshires in the Fall offers fiery foliage, pumpkin patches, crisp air at the ...

  19. Best Places In Massachusetts To Visit In The Fall

    Cape Ann. Once one of the best places to visit during summer, Cape Ann becomes even better during Fall. You'll find many things to do and see on the water, as well as some fantastic views of the fall foliage. Also, make sure you visit Gloucester and Rockport during your trip, both of which are highly recommended by previous visitors.

  20. 10 Best Small Towns in Massachusetts

    Located just 20 miles outside of Boston, Concord is one of the state's most accessible small towns. The community is best known for its divine outdoor spaces like Walden Pond, which inspired ...

  21. 10 Of The Least-Crowded Towns To Visit In Massachusetts To See Fall Foliage

    Massachusetts is home to charming small towns with stunning fall foliage displays, offering a peaceful alternative to popular tourist destinations. Lenox, Stockbridge, and Northampton are among the least-crowded towns in Massachusetts during fall, featuring vibrant autumn scenery and attractions. Visitors can enjoy activities such as hiking ...

  22. 8 Best Places To Visit In Massachusetts In The Fall Season 2023

    Mount Greylock Summit. The Mount Greylock Summit in the Berkshires is the highest point of elevation in Massachusetts. Visitors can either hike or drive to the top. On a clear day, you can see up to 90 miles in the distance. The town of Adams is at the base of the mountain, and there are various inns and campgrounds to stay in nearby.

  23. 10 Things To Do In Pioneer Valley: Complete Guide To This Scenic ...

    Here are the top things to do in these must-visit small Massachusetts towns. Visit The Naismith Memorial Basketball Hall Of Fame The popular game of basketball was invented in 1891 by James ...

  24. 10 Places To Visit In Massachusetts This Fall (That Do Not ...

    8 Discover Quabbin Reservoir In Central Massachusetts. The largest inland reservoir in Massachusetts, Quabbin Reservoir, offers outdoor activities, including fishing, boating, and walking. Located in Belchertown, the reservoir features 180 miles of lake coastline and sprawls over 39 square miles. Visiting at the height of the fall foliage ...

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