travel to winter park

Your browser is not supported for this experience. We recommend using Chrome, Firefox, Edge, or Safari.

Find Your Favorite Beach

Atlantic Coast

Beach Camping

Family-Friendly

Places to stay.

Campgrounds

Travel Ideas

Accessible Travel

Eco-Friendly Travel

African American Heritage Travel

More Travel Ideas

Popular links.

Florida Webcams

Toll Roads Info

Travel Guides

What to do in winter park, florida: the perfect weekend itinerary.

By Ana Connery

Winter Park , a city of 25,000 just five miles north of downtown Orlando, has been a tony retreat pretty much since it was first developed in the late 1800s by wealthy northerners who wanted to take advantage of the lakeside setting.

The entrepreneurs drew plans for a city that would embrace the park-like setting and provide opportunities for local businesses to thrive.

Today, Winter Park still feels more town than city , with its walkable grid of brick-paved streets flanked by a European style of architecture that celebrates Gothic arches, clay-barrel roofs and intricate ironwork. Wandering around is a must.

Park Avenue is Winter Park’s main artery, running for eight blocks from Rollins College to the Charles Hosmer Morse Museum of American Art before fading into a residential neighborhood shaded by moss-draped oaks.  

Winter Park feels more town than city, with its walkable grid of brick-paved streets flanked by a European style of architecture that celebrates Gothic arches, clay-barrel roofs and intricate ironwork.

- Julie Fletcher for VISIT FLORIDA

Park Avenue is Winter Park’s main artery, running for eight blocks from Rollins College to the Charles Hosmer Morse Museum of American Art before fading into a neighborhood shaded by moss-draped oaks.

Art and Academia

As you stroll the garden paths and side streets, a sense of collegiate history echoes, but perhaps no more so than at the new Alfond Inn . Long a popular getaway for the nation’s elite, including President and Mrs. Reagan, who celebrated their 25th wedding anniversary here, what was then the legendary Langford Inn sat empty for years.

Eventually a pair of Rollins alumni, Ted and Barbara Alfond, invested millions to rebuild it in part to showcase their extraordinary art collection, the centerpiece of the Cornell Fine Arts Museum on the nearby campus. The renowned art lovers wanted the 112-room hotel to serve as much as a “visual syllabus” as a place for students’ parents and visitors to lay their head.

Check in on a Friday afternoon and the myriad courtyards and conservatory will likely be abuzz with well-heeled locals kicking off the weekend with one of the bar’s happy hour specials. Having a drink in hand is not a bad way to embark on a self-guided tour of the contemporary art collection found primarily on the first and second floors. It's a must-see for an art lovers.

From high-energy video to neon signs that promote the Alfond’s mission with words like, “Language must speak for itself,” the collection’s highlights include “Afghan Girl,” the famous photo by Steve McCurry that graced the cover of National Geographic and is commonly referred to as the Afghan Mona Lisa.

A group of 19 paintings of the covers of famous books comprises a collection that connotes the intellectual curiosity of the Rollins faculty members who chose the works as their fave pieces of literature.

To experience activities rich in culture, walk north on Park Avenue past the many family-owned jewelry shops, cafes and boutiques tucked in between preppy chain stores to the Morse Museum , where admission is free every Friday between 4 and 8 p.m. except during summer.

If you get tired of walking, take a two-wheeled adventure down the city streets.

Winter Park's wide variety of restaurants means there is something for everyone.

The draw here is the exquisite glass art of Louis Comfort Tiffany, the most comprehensive collection of his work in the world. His chapel interior, the original from the 1893 World’s Columbian Exposition in Chicago, is as full of detail and spiritual prowess as any you’d find in Europe.

The galleries featuring the ornate art and furnishings from his famed Laurelton Hall residence on Long Island provides a peek at what an artist can do with enormous wealth (Tiffany’s father was the founder of the famed Fifth Avenue jewelry store in New York).

Stop for dinner at Prato on Park Avenue, where a floor-to-ceiling glass storefront opens to reveal a seamless transition from the inside out.

Ask for a table near the sidewalk so you catch the scent of the Central Park rose garden across the street and watch Amtrak trains shuffle passengers in and out of the town depot. With a setting like this, you’ll be tricked into thinking you’ve gone back in time—with more appropriate clothes.

There are few light dishes at Prato, but the modern Italian cuisine does subscribe to the trendy farm-to-table approach to food with many local farmers highlighted on the menu. Start with the savory meatballs in a roasted tomato pulp before indulging in the Widow Maker pizza from the wood-burning oven in the open kitchen. Topped with fennel, sausage, prosciutto and a sunny-side up egg, it’s a hearty take on a popular dish. You’ll be glad for the walk back to the Alfond Inn.

Natural Wonders

Wake up early to beat the crowds at the Winter Park Farmer’s Market just two blocks west of Park Avenue. Next to produce and plant stands from nearby farms, a lineup of food stalls and trucks serve everything from French croissants to fresh smoothies.

Inside the adjacent brick building that once housed the original Winter Park train depot, you’ll find fresh bagel sandwiches as well as homemade pastas and cheeses. Sit on the breezy patio to enjoy your breakfast before peeking into the Winter Park History Museum at the northern end of the building. Run by volunteers, it features rotating exhibits that showcase the history of the city, including a recent retrospective of the local high school.

Spend the afternoon partaking in activities at the Alfond Inn’s rooftop pool with its tree-line view of the apartment building across the street. Sir Paul McCartney reportedly bought the top floors for his stepson, who attends Rollins College.

Catch the sunset during the last Winter Park Scenic Boat Tour of the day. From the dock on the east end of Morse Street, this family-owned business has been taking passengers across three of the seven lakes on the tranquil Winter Park chain since 1938. Besides great views of the sprawling backyards of the city’s wealthiest residents, you’ll sneak a peek at the beautiful Rollins campus and might even catch a gator or crane sunbathing along the mangroves as you slide across two narrow canals.

Sunday stroll

Come Sunday, if it hasn’t already, Winter Park makes it clear this is a playground for the upper crust. Stroll west past the cardigans and linen pants toward Hannibal Square , a section of the city originally designed as a separate community for African Americans.

The two blocks here are like a mini Park Avenue of fine restaurants and specialty shops.

On the rare weekend that a festival of some sort is not in full swing, wrap the weekend with a little window shopping at Tuni , a trendy boutique owned by a local mother and daughter. Linger over the baubles at another family-owned biz, Simmons Jewelry , and the handcrafted home accents at Ten Thousand Villages before sliding into a sidewalk cafe for one last taste of the Florida good life.

For more about Winter Park, visit www.cityofwinterpark.org .

Places to Remember

Winter Park

Related content.

The Alfond Inn

• 300 E. New England Avenue
• (407) 998-8090

Winter Park Chamber of Commerce

• 151 W Lyman Avenue
• (407) 644-8281

City of Winter Garden

• 300 W Plant Street
• (407) 656-4111

STRATEGIC ALLIANCE PARTNERS

• Winter Park Resort
• Winter Park Ski In Ski Out Lodging
• Town Of Winter Park
• Fraser & Surrounding Area
• Pole Creek Golf Club
• Ski In Ski Out
• Luxury Collection
• Private Homes
• Pet Friendly
• New Properties
• Long Term Rentals
• All Winter Park Lodging
• Properties A-Z
• Ski Rental Deals
• Lodging Deals
• Activity Deals
• Lift Tickets & Passes
• Winter Park Tips
• Winter Park Guide
• Transportation Options
• Getting Around
• Live Cameras
• Prospective Homeowners
• Contact Owner Team
• Owner Login
• Guest Reviews
• Our Policies
• Steamboat Springs

Three Easy Ways To Get To Winter Park

So you made it to Denver… now how do you get to Winter Park? Located just 90 miles from the Denver International Airport, Winter Park is an easy drive, short shuttle ride or a quick train ride away. With all the available transportation options, we promise you can get to the mountains quickly to start your unforgettable vacation

1. RENT A CAR NEAR THE DENVER INTERNATIONAL AIRPORT

The most popular (and convenient) way to get to Winter Park is to rent a vehicle and, luckily for you, we’ve got deals with Alamo , so don’t forget to request a quote when confirming your vacation with us. We always recommend getting a rental with AWD or 4WD, especially in the winter season. Because when the mountains are calling, it’s necessary to have the correct vehicle to conquer them.

Winter Park is situated about 90 miles from Denver International Airport, and the drive can take up to two hours depending on weather and road conditions. We highly recommend checking CDOT’s website before making the trip to Winter Park to get a heads up on any delays or closures to expect. The most direct route is to hop on I-70 and take the exit for CO-40 right after Idaho Springs. If your stomach’s grumbling, pull off here and check out Beau Jo’s for your first taste of “Colorado Style” pizza. What’s the secret? Not only is honey mixed into the fresh dough, but it’s on the table to drizzle onto your crust as well! After your pizza fix in Idaho Springs, hit the road again but be sure to slow down and check your speed through the town of Empire It’s easy to miss that the speed limit has lowered, and we don’t want you getting a ticket before you arrive. Even though you’re only about 20 miles away at this point, Berthoud Pass can take a bit of time. Steep grades and several switchbacks make this short stretch time consuming but worth it with amazing views of the Continental Divide.

LOCAL’S TIP: Pull off at the summit of Berthoud Pass to grab a shot of the road winding up & down the mountainside and marvel at the journey you’ve just made. Take a selfie here, you won’t regret it!

In the summer, you can also meander over Trail Ridge Road (the highest paved road in Colorado), through Rocky Mountain National Park . While the full route will take you about four hours, it will not disappoint! Trail Ridge Road can be assessed from Estes Park or Grand Lake; it covers almost 50 miles through the park and reaches elevations of over 12,000 feet. Make time for a pit stop at the Alpine Visitors Center for breathtaking views. If you start in Estes Park and finish in Grand Lake, take a minute to enjoy the largest natural body of water in Colorado (another great photo op). Stop for a bite to eat at the Sagebrush BBQ & Grill , where you’ll find something for everyone on the menu. Kids and adults alike will delight at the buckets of peanuts on the tables, and you’re even encouraged to throw the shells on the floor! Hop on CO-40 from here, and you’re only about 45 minutes away from your mountain getaway in Winter Park!

2. AIRPORT SHUTTLE TO WINTER PARK

If driving yourself seems exhausting, another popular option is booking a shuttle. Home James Transportation Service is everyone’s top choice, with airport pickup and front door drop off! With regularly scheduled shuttles and private charters, Home James is convenient and stress free. Be sure to get your tickets in advance, though, because it’s no secret that Home James is the preferred service in the area. 

LOCAL’S TIP: Keep in mind there are no car rental companies in Winter Park, so if you take a shuttle to town from the airport, you’ll have to rely upon public transportation or ride sharing (when available) while you’re here.

3. SCENIC TRAIN RIDE TO WINTER PARK FROM DOWNTOWN DENVER

If you prefer to travel at a slower pace, you could take the old-fashioned way and hop on a train! The legendary California Zephyr departs from Denver’s Union Station daily at 8AM. The unforgettable ride is just over two hours, and gives you a great opportunity to relax and check out the mountain vistas. The Zephyr drops you off in Fraser, with a free Lift bus stop just steps from the platform. Busses run every 30 minutes during peak season, and every hour in the off season.

LOCAL’S TIP: Don’t forget to make your way to the scenic viewing car, where the windows stretch up into the ceiling to afford unforgettable memories. 

During the ski season, Amtrak runs a special ski train, The Winter Park Express , running between Denver and the resort on the weekends.  This limited run will drop you off at the base of the ski area, just 100 feet from the lifts.  Advance booking is highly encouraged, as this popular train tends to sell out.

Now matter how you get to Colorado’s Playground, we promise you won’t forget your incredible vacation in Winter Park.

Quick Links

• Vacation Rentals

Find A Property

Copyright © 2024 Winter Park Lodging Company. All Rights Reserved. Web Design by InterCoastal Net Designs

ONE CHEL OF AN ADVENTURE

Everything you need to know about visiting winter park resort.

Looking for a great place to take a ski trip? Winter Park Resort was named the #1 Ski Resort in North America by USA Today ! 

With over 3,000 skiable acres, 7 distinct areas for every skill level, and more than 315 inches of annual snowfall, Winter Park Resort is sure to impress on your next ski trip! Here’s the rundown on everything you need to know about visiting Winter Park Resort :

I was invited by Winter Park Resort to visit their property in exchange for coverage on social media and my blog, however, all opinions and statements are my own!

Visitor's Guide: Winter Park Resort, Colorado

How to get to winter park resort.

The best way to get to Winter Park, CO is by flying into the Denver Airport. From there, you have several options on how to get out to Winter Park Resort (about a 2 hour drive). 

Rent a Car in Denver

You can rent a car right at the airport, however, take into consideration that you will be driving on snowy, icy roads. If you’re someone like me, who’s from Texas and have never driven in snowy conditions, this might not be your best move.

Also, at first glance, it may look like it’s cheaper than some shuttle options, but you’d probably need to get an SUV with 4-wheel drive, and that is considerably more expensive than the budget vehicle!

Take a Home James Shuttle

This is the option we chose. We booked with Home James Transportation and were pleased with the experienced! It was a little tight inside, but not too uncomfortable. Both drivers we had were incredibly kind and very knowledgeable about the area. Plus, Home James drops off right to your hotel!

Though you have less control over when you leave and arrive ( see schedule here ),  it’s so worth it to take a shuttle and not have to worry about driving in snowy conditions. 

If you have a group of 6 or more, it works out that renting a private shuttle is cheaper, which would be even better! Above photo from the Home James Facebook.

Take the Winter Park Express Train

During the peak winter months, you can take the Winter Park Express Train from downtown Denver’s Union Station. While it’s less expensive than the other two options ($29 one way when I checked), it only runs on Saturday and Sunday and the first two Fridays of every month. 

You would have to take the A-Line train from the Denver Airport to get to Union Station downtown, then switch over to the Winter Park Express train . If you have a lot of luggage, this would definitely be a hassle. Plus the train only drops off at the station, meaning you’d then need to carry your luggage from there to wherever you’re staying.

I think this is really only a good option if you already live in Denver, but wanted to lay out all the options!

Where to Stay in Winter Park Resort

We stayed in a Zephyr Mountain Lodge condo , and would definitely recommend it! We had a nice two-bedroom condo, that overlooked the mountain. It had TV and Wifi, and was just steps from the base of the mountain and gondola.

It also had a nice hot tub overlooking the slopes too — perfect for after skiing!

They have many other lodging options, browse them here .  I would definitely recommend staying in or near “the village.” It’s close to everything and super convenient! PS: my cute pom pom hat is crazy warm and under $15  on Amazon !

Related Post:  How to Prevent Altitude Sickness in Colorado

Skiing in Winter Park Resort

As Winter Park Resort was named the #1 Ski Resort in North America by USA Today , of course, you MUST ski when visiting! 

We rented our ski gear from Mountain Adventure Center , right at the foot of the mountain. They even held on to it there for us until the next day so we didn’t have to lug it all up to our hotel room and back!

We rented our ski pants and jackets from Kit Lender, read more about it here .

We did a 2-hour guided mountain tour . This was a great option, but, if you haven’t skied in awhile, I would highly recommend doing  a lesson first .

If you are pretty comfortable on skis, then I would say definitely go for a guided tour ! They take you all around the mountain showing you the best runs for your comfort level. Plus, you get to skip all the lines when you’re with a guide!

It is so beautiful up on the mountain, I can totally see why it was voted the #1 Ski Resort!

After you finish skiing, you MUST head to Sunspot Lodge ! located on top of the mountain, Sunspot offers amazing views of the continental divide and all of Winter Park at 10,700 ft!

Related Post:  Everything You Need to Pack for a Winter Ski Trip

More Activities To Do

Of course skiing is the main attraction at Winter Park Resort — they weren’t ranked #1 for nothing 😉 — but there are  so many other fun things to do while visiting Winter Park Resort !

SnowCat Tour

The SnowCat Tour is an awesome way to see the mountain from the comfort and warmth of being inside a vehicle (I think that’s what it technically is? haha). 

However, I do not recommend booking a tour for the evening. It gets dark around 5:30, so 75% of our tour was dark and we couldn’t see anything. Had we gone during the day though, it would have been amazing! So book either the 10 AM, 12 PM, or 2 PM tour!

Tubing at Coca-Cola Tube Park  is a fun activity that everyone will enjoy! There are 4 different lanes with banked curves and varying speed, so it’s even great for younger kids.

Snowmobile Tour

Snowmobiling was hands down one of my favorite parts of this trip! I had never done it before, and now I am hooked! I would say this is one NOT TO MISS!

Other Activities

As much as we would’ve loved to have done every activity in Winter Park Resort, time didn’t allow. These are some other activities that are worth checking out (I just can’t speak on them personally):

• Snowshoe Tours
• Ice Skating
• Sleigh Rides
• Dog Sled Rides
• Ski Bike Tour

Winter Park Resort truly is a great place to take a ski trip, you will not be disappointed! Have any questions? Feel free to comment or send me an email and I’d be happy to answer them!

You Might Also Like:

• Ultimate Winter Ski Trip Pack List
• Review: Staying Devil’s Thumb Ranch in Tabernash, CO
• Snowmobiling Tour at Winter Park Resort, Colorado – A MUST DO!

Vail, Colorado in Summer: Best Things to Do, See, and Eat

Estes Park, CO: Best Things To Do, See, and Eat

Grand Lake Lodge – Best Hotel in Grand Lake, CO

Snowmobiling Tour at Winter Park Resort

Colorado Packing List for Summer – What to Pack for Summer Hiking in CO

Four Seasons Resort Vail – REVIEW

Liked this post? Pin to Pinterest!

Share this:

8 thoughts on “ everything you need to know about visiting winter park resort ”.

• Pingback: Staying at Devil's Thumb Ranch
• Pingback: Snowmobiling Tour at Winter Park Resort
• Pingback: Everything You Need to Pack for a Winter Ski Trip - Snow Packing List
• Pingback: Altitude Sickness in Colorado: How to Treat + Prevent It
• Pingback: One Chel of an Adventure: 2019 My Year in Review
• Pingback: Best USA Honeymoon Destinations by Season - USA Honeymoon Ideas

Hey, I read a lot of your articles and all the articles are very informative. I’ve got a great idea for a post that I believe would do well. I’d love to send some original content your way. I’m already writing regularly. Let me know if you are interested. Hope to get a positive response from you. Thanks

• Pingback: Ski Trip Destinations for Spring Break - Where to go for a Ski Spring Break

Leave a Reply Cancel reply

This site uses Akismet to reduce spam. Learn how your comment data is processed .

Discover more from ONE CHEL OF AN ADVENTURE

Subscribe now to keep reading and get access to the full archive.

Type your email…

Continue reading

Travel Resources

Getting here.

Enjoy your trip to Winter Park completely car-free by using transit options such as the Outrider bus service which can take you from Denver Union Station or the Federal Center-Lakewood directly to Winter Park. The Winter Park Express is a seasonal train between Denver Union Station and the doorstep of the ski resort. Once you arrive, use the free Lift bus service to get around Winter Park and neighboring towns. There are multiple airport shuttle services to transport you from DIA. Learn more about the many options available to get from the Denver metro area to Winter Park at www.GoI70.com/transit .

Want to try carpooling? Use TreadShare , a carpool app that connects drivers and passengers heading in the same direction in Colorado so they can share a route and split the associated costs.

Pro tip: Use GoI70’s travel forecast to help plan the best time to travel to avoid traffic!

In Winter Park, we aim to be good neighbors to each other. Whether a permanent resident or visiting for a long weekend, we’re respectful of our town, our homes, our environment, and each other. We work together to solve problems and make it a place everyone can live!

As our town evolves, we need to make sure that driving isn’t the only option for getting to work, school, or your favorite trail. Travel by bus, bike, foot, or skis are all viable - and fun - options for our community. It’s easy to navigate Winter Park within Town limits, but it’s also easy to get to Denver or the Front Range.

It’s no secret that many of us live here for the boundless outdoors - we have gorgeous mountains, rivers, and forests that bring in people from all over the world. Let’s celebrate it and embrace this part of our culture!

Our pristine natural environment is what sets our community apart. Protecting our forests, rivers, mountains, and fresh air is critical. Visitors and locals rely on the natural environment for recreation, jobs, and inspiration.

 Welcome to Winter Park Travel

Established in 1982, Winter Park Travel  provides complete travel services for Fraser Valley and our clients all over the world. Contact Winter Park Travel today to get your trip started on the right foot.

At Winter Park Travel, Inc., we take pride in offering the best customer service in the industry, including 24/7 access in case of emergencies!  We know that you have many choices when booking travel, and our goal is to ensure that you’ll always want to choose us!

Colorado offers many wonderful ski resort options. Here is a sneak peak of the offering that Winter Park ski resort offers. Let us take care of all of your arrangements while you enjoy the beauty of colorful Colorado and the world renowned Rocky Mountain powder.  Rockies and the freshly fallen snow.

Living in Winter Park our entire lives we know our Colorado ski resorts inside and out so we can provide you with the perfect travel package and ski accommodation to fit your needs.

Winter Park Travel has a lot to offer:

Choose from any of the below activities and packages

Ski Packages

Summer vacations, a few words from one of our happy customers.

He has a really special ability to understand the needs—the sometimes contradictory needs—of alpine ski racing. Like you want to know with great certainty everything, but you have no idea when you want to go because there isn’t snow there yet or you don’t know how big your group is.

Green Mountain Valley School

Years in Business

Satisfied clients.

• Search Please fill out this field.
• Manage Your Subscription
• Give a Gift Subscription
• Newsletters
• Sweepstakes
• Destinations

This Charming Florida City Near Orlando Is the Perfect Break From the Theme Park Crowds

Even though Winter Park is near Orlando's theme parks, it feels leaps and bounds away.

Wirestock/Getty Images

Cobblestone streets dotted with Michelin-recognized restaurants and locally owned shops, lakes with boat tours, and grassy areas for kids to play tag and fly kites: This is Winter Park, Florida. A hop, skip, and a jump from Orlando’s theme park scene, this town chartered in 1887 thrills in other ways. Its original purpose still holds true: New Englanders founded it as an escape from cold weather. But since that time, the 10-square-mile city has become a year-round destination. Orlando residents love the place, but they can’t keep it a secret anymore. No matter why you’re in the Orlando area, a few days in Winter Park would provide a welcome respite before heading home. In fact, the town has so much going for it, we’d argue that it merits a trip on its own.

Downtown, Park Avenue — where stand-out restaurants and local boutiques dot the brick streets — is the place to be. Just off Park Avenue, Rollins, a small liberal arts college founded 135 years ago, contributes to the town’s robust array of cultural activities. A short walk from downtown lies the waterfront, where six lakes are connected by navigable canals. Ready to plan a trip to this charming city? Here's what you need to know.

Education Images/Getty Images

Best Things to Do in Winter Park

If you like culture, nature, and shopping, Winter Park will be a new favorite. With a rose garden and beautiful fountains, 11-acre Central Park on Park Avenue hosts many of the city’s festivals and events, including holiday festivities and the Olde Fashioned Fourth of July Celebration. It’s also the perfect place to take the kids to burn off steam in between visiting stores or before going back to the hotel.

More spectacular than you’d imagine, the Morse Museum , located on Park Avenue, features a large collection of Tiffany works as well as other American art. The stunning chapel, which was crafted for the Chicago World’s Fair, is a must-see.

When you’re ready for a break from walking, take the hour-long Scenic Boat Tour around Winter Park’s many lakes, where you'll spot beautiful homes while you learn more about the city's history. Kids of all ages are welcome (even encouraged) to join the fun on the 18-passenger pontoon boats. Water sports, like paddleboarding and kayaking, are also popular around the lakes.

On Saturday mornings, dozens of vendors sell their produce, bread, sweets, and more at the Saturday Farmers’ Market . It's the perfect place to grab ingredients before heading to a park for a picnic lunch.

Save room in your suitcase to treat yourself to an item from one of the many one-of-a-kind shops in Winter Park. You’ll swoon over the stationary and artsy decorative items at Rifle Paper Co. ’s own store (the brand is based in Winter Park).

Local teens and college students shop at Avalon Exchange , a thrift shop that’s clean, organized, and budget friendly with a mix of retro and popular brands. Stop by Loving Thyself Rocks if for nothing else than to get a selfie sitting on the winged crystal chair at the entrance. Writer’s Block bookstore offers a well-curated selection for kids and adults (plus a fantastic name).

Winter Park Hotels

While visitors only have a handful of lodging options in Winter Park, the surrounding area opens up a multitude of possibilities.

Established more than 130 years ago, The Alfond Inn at Rollins is getting better with age. Sprinkled with incredible paintings from the Rollins Art Museum, the recently renovated lobby is a design masterpiece and fosters family togetherness thanks to a variety of seating arrangements and a corner chess set. An expansion, which will add a new spa and a wing to the inn’s current 112 guest rooms, is expected to wrap up by the end of the year. The location, just a few blocks from Park Avenue, is stellar.

With 28 guest rooms — some with original brick walls — the Park Plaza Hotel is the only place to stay on the city’s famed Park Avenue. There are balcony rooms and suites for people-watching.

About eight miles from Winter Park, Sonder Wellborn is located in the oldest house in the Orlando area. Suites are well priced and spacious, plus the property includes a Victorian garden.

If you’re combining a business trip to the Orlando Convention Center with a visit to Winter Park, the AC Hotel Marriott Downtown Orlando is a great choice. The eight-floor, 180-room property boasts a SkyBar Rooftop Terrace with incredible city views. It’s just eight miles from Winter Park.

Visit Florida

Best Time to Visit Winter Park

While you’ll have fun no matter when you go to Winter Park, shifts in weather and special programming favor certain months.

Despite its name, the most comfortable season to visit Winter Park is spring — and the earlier, the better. March feels glorious with average high temperatures reaching about 76 degrees Fahrenheit and the lowest humidity of the year. It’s no coincidence that the organizers of the city’s annual Sidewalk Art Festival, which attracts 350,000 visitors, schedule it for March. It’s a little cooler in February and warmer in April, but still pleasant. You won’t find many April showers in Winter Park — April is the second-least rainy month.

The holidays usher in another magical time to explore Winter Park, especially if you’re bringing children. Two big events take place during the first weekend of December. On Friday, “Winter on the Avenue” transforms Central Park into a holiday wonderland, complete with snow slides, s’mores, and strolling carolers. Everyone gathers around for the lighting of the Christmas tree and menorah. The next day, music fills the streets for the Ye Olde Hometown Christmas Parade. A tradition for more than 70 years, the parade’s headliners include marching bands, fire trucks, and Santa Claus. Winter Park’s weather by far outshines the North Pole, with average December highs in the mid-70s.

Families who have to plan their vacations around school calendars and practice schedules may not be able to avoid a summertime visit. Although it’s typically hot, humid, and rainy, scheduling outdoor activities for the morning or evening will make it less likely that Florida’s temperamental summer weather will interfere with your fun.

Where to Eat and Drink

Orlando locals flock to Winter Park for memorable meals — whether they’re bringing the entire family or looking for a romantic table for two. Winter Park serves up a variety of cuisines and vibes at its top food establishments.

At Briarpatch , the most iconic eatery on Park Avenue, locals line up for mimosas and delicious brunch offerings (think: brown butter Belgian waffles and raspberry lemon cream pancakes.) The housemade cakes — carrot, chocolate layer, and red velvet — are as Instagrammable as they are tasty. You can dine al fresco on the outdoor tables overlooking Central Park or opt for the indoor seating; the dining room oozes Southern charm.

Fresh from earning a Michelin star, Soseki , a 10-seat Japanese restaurant, specializes in a divine multi-course dining experience based on the best ingredients that its farmers, fishermen, and cheese purveyors offer.

With husband-and-wife, James Beard-nominated chefs in the kitchen, The Ravenous Pig hits the spot with a variety of apps, hand-helds, innovative cocktails, and other gastropub fare.

If the kids want pizza, Prato is the place for your family. Request a table on the patio (isn’t there something about eating outside that makes kids less wiggly?) and order them a margarita pie to share while you pick one of the other modern Italian dishes made with locally sourced ingredients.

Getting There

Winter Park is easily accessible by car and airplane. You probably won’t use your car much once you’re in town.

If you’re coming from one of Orlando’s theme parks, the ride will be relatively short. Winter Park is about 30 miles north of Disney’s Magic Kingdom and 15 miles north of Universal Florida on I-4. Tampa, Jacksonville, and Melbourne, Florida are all within two hours or so.

The closest airport is Orlando International Airport, which is about a 30-minute drive to Winter Park. Later in 2023, the Brightline Train’ s airport station will connect the city with Miami, Boca Raton, West Palm Beach, and Fort Lauderdale. If you can fly into the smaller (and far less crowded) Orlando Sanford International Airport, you’d still only have about a half-hour drive.

Related Articles

We Are Travel Girls

A Community Created To Inspire, Connect, Educate & Empower Female Travelers

FLORIDA , NORTH AMERICA , UNITED STATES · February 17, 2024 Last Updated on March 10, 2024

A QUICK GUIDE TO WINTER PARK, FLORIDA

This post may contain affiliate links. As an Amazon Associate I earn from qualifying purchases. We may receive a small commission when you make a purchase using our link.

The quaint town of Winter Park is straight out of a fairytale. Winter Park is located just north of Orlando and is a lovely place for a winter escape. Some of the most notable things in Winter Park are the amazing restaurants, charming brick streets, and year-round sunshine.

Orlando is a highly sought-after destination because it is home to the famous Disney World. So Winter Park is a great place to visit if you have an extra day on your Disney trip. This ultimate guide to Winter Park, Florida will go over where to stay, what to do, where to eat, when to visit, and more.

Where To Stay In Winter Park, Florida

Since Winter Park is a tiny town, there are not a ton of hotel options, but these are my favorite Winter Park Hotels.

• Park Plaza Hotel – The Park Plaza Hotel is located right on Park Avenue and truly captures Winter Park’s charm. Winter Park has an old-fashioned feel to it, and so does the Park Plaza Hotel. Admire the antique decor and the southern hospitality the staff provides at the Park Plaza. Each morning, you will be greeted in your room with warm croissants and freshly squeezed orange juice. The Park Plaza is a lovely, budget-friendly hotel in Winter Park.
• The Alfond Inn – Located just across from the gorgeous Rollins College is The Alfond Inn. The Alfond Inn provides comfortable, clean rooms with a modern feel. Enjoy the outdoor swimming pool, fitness center, spa, bar, and more at The Alfond Inn. The Alfond Inn is a great option if you are looking for a luxury option in Winter Park.
• The Delaney Hotel – While not technically in Winter Park, The Delaney Hotel is a great place to stay while in the Orlando area, and is a short 15 minutes away from Winter Park. The boutique hotel offers cozy, modern rooms, a delicious in-house restaurant and bar, a fitness center, and more.
• The EO Inn – Tucked away in downtown Orlando is the reasonably priced EO Inn. The EO Inn has everything you need for a relaxing getaway in the sun – a rooftop patio, a restaurant, comfortable rooms, a great location, and more. The EO Inn is around ten minutes from Winter Park.
• Hilton Garden Inn Winter Park – Located on Lee Road, this hotel offers guests free self-parking and a bar. The hotel has rooms which can sleep up to five people comfortably.
• SpringHill Suites by Marriott – Just a short drive from Rollins College and the Orlando Science Center. The hotel has 126 rooms with a mix of a family room, king suite, and executive suite.

Best Things To Do In Winter Park, Florida

1) take a stroll down park avenue.

The charming Park Avenue is home to insanely good restaurants, unique shops, and adorable boutiques. Park Avenue has everything you need for the perfect shopping extravaganza. Some of my favorite shops on Park Ave are  Adjectives Home Decor ,  Writer’s Block Bookstore , and  EVEREVE women’s clothing.

Not only is Park Ave home to amazing restaurants and boutiques, but it is also pulchritudinous. The brick road and perfectly manicured park in the middle of Park Ave make for a relaxing day.

While on Park Ave, stop at the Central Park Fountain and the Peacock Fountain.

2) Winter Park Scenic Boat Tour

Winter Park is home to stunning lakes (Lake Virginia, Lake Mizell, Lake Berry, and Lake Osceola) all of which are connected. The Scenic Boat tour brings you through all of these lakes. If you want to enjoy nature and learn more about the history of Winter Park through a scenic boat tour, this is for you!

You can book your spot on the boat tour here or you can buy your tickets at the docks. The docks are an easy walk from Park Ave. For an adult, you will pay $20.00; for a child, you will pay $10.00.

3) Play A Round Of Golf

Winter Park, and Orlando in general, is home to some amazing golfing. Located just off of Park Ave, the Winter Park Golf Course provides golfing for all ages and levels. Whether you are a veteran or a beginner, golfing is a great activity to try in Winter Park!

4) Explore Hannibal Square

Hannibal Square is a great place to grab some food, shop, or admire the beautiful buildings and flowers. While Hannibal Square is much smaller than the nearby Park Avenue, it is quieter and more of a local spot. My favorite restaurants in Hannibal Square are  Pepe’s Cantina Mexican Grille  and  Armando’s .

Make sure you pop into a few boutiques – I love  Rifle Paper Company .

5) Take a Tour Of Rollins College

Even if you are not a prospective student, Rollins is totally worth a visit. The campus is beautiful! Located on the stunning Lake Virginia, Rollins is home to beautiful Spanish architecture and fabulous green spaces and makes for the perfect place for a leisurely walk.

There is a short path by Lake Virginia that offers great views.

6) Have a Picnic In Mead Botanical Garden

Mead Botanical Garden is quite the hidden gem. The easy-to-navigate botanical garden is located just south of Park Ave. At Mead Botanical Garden, you will find trails, boardwalks, gardens with unique plants, outdoor theaters, and more.

If you are traveling with a dog, Mead is a great place to walk your pup or go on a jog. You can also find more activities in Mead, such as yoga and guided hikes.

Best Tours To Take From Winter Park, Florida

Winter Park is a great place to visit and explore around Orlando, but it’s also a great place to stay for a trip to the wider city. Here are some of the best tours to take in or from Winter Park, Florida.

• Get access to over 25 popular Orlando attractions, tours, and more with Go City’s All-Inclusive Pass and save up to 50%. Enjoy top destinations such as Kennedy Space Center, Legoland, The Wheel at Icon Park and others.
• Explore the entire 4,200 acres of protected swamps, marshes, and rivers that form the Central Florida Everglades; you can explore the Everglades on an airboat tour .

What To Eat In Winter Park, Florida

Coffee and breakfast in winter park.

• Foxtail Coffee Company – Foxtail Coffee Company is a lovely place to grab quality coffee while in Winter Park. Working with farms from all over the globe, Foxtail has the perfect space for working, chatting, and relaxing. Not only does Foxtail serve some seriously good java – but they also serve breakfast, lunch, and dinner in their casual environment.
• Framework Coffee Bar – Hidden off the beaten path is Framework Coffee. Framework prides itself on being locally sourced and sustainable. The aesthetically pleasing coffee shop is perfect for grabbing a fancy latte or a quick cup of coffee.
• Briarpatch – Briarpatch is Winter Park’s best breakfast and brunch spot. At Briarpatch, you will find everything from breakfast to brunch. The pancakes are my favorite, but you really can’t go wrong. Saturdays and Sundays fill up very fast, so be sure to plan ahead.

Lunch and Dinner In Winter Park

• Prato – Prato is a lovely Italian joint on Park Ave. Prato is a fan favorite in Winter Park, serving up affordable yet quality pasta, pizza, salads, and more. If you are planning on eating at Prato over the weekend then be sure to make a reservation.
• Orchid Thai Cuisine – Orchid is my favorite Thai place in Winter Park. Located on Park Ave, Orchid serves up some amazing curries, stir fry, spring rolls, dumplings, and more. Orchid never gets too busy, so there is no need to make a reservation.
• Black Bean Deli – Black Bean Deli is my go-to takeout place in Winter Park. The Cuban restaurant is a casual, grab-and-go type place but also offers seating. Open since 1835, not only does Black Bean Deli make delicious food, but it also has a fascinating story. Read about Black Bean Deli .
• SoDough Pizza – You cannot go to Winter Park without trying the mouth-watering SoDough Pizza. SoDough provides Detroit-style pizza that will blow your socks off. You can find classics such as regular cheese and unique pies like the Big Mac Attack modeled after Mcdonald’s Big Mac.

Dessert In Winter Park

• Croissant Gourmet – Located on Park Ave is Croissant Gourmet, an adorable little French Bakery. Croissant Gourmet is the perfect place to go if you are craving something sweet. Croissant Gourmet has amazing crepes, french desserts, coffee, and croissants.
• AJ Chocolate House – This European chocolate house is the perfect place to go for an after-dinner treat. AJ Chocolate House on Park Ave offers sweet luxury and comfortable seating.

When To Visit Winter Park, Florida

My favorite month in Florida is March – the weather is perfect! Fall and summer can be tricky because they are hurricane seasons, and they are usually extremely hot.

The winter and spring are lovely times to be in central Florida because you will be able to enjoy sunny, mild days and avoid winter if you are coming from the north.

Getting Around Winter Park, Florida

Winter Park is quite walkable. If you are staying on Park Ave you can walk to Hannibal Square, Rollins College, The Winter Park Golf Course, and the Scenic Boat Tour. Mead Garden is a mile walk from Park Ave so it is also doable.

If you are staying in Winter Park for your whole trip, renting a car is unnecessary. Just Uber to Winter Park from Orlando International Airport.

If you are just taking a day trip to Winter Park from Orlando, you can take the train from the center of Orlando to Winter Park (the train station is on Park Ave). Trains run every 30 minutes and will only set you back $2. Purchases train tickets here .

Winter Park, Florida Wrap Up

Winter Park is an adorable fairytale town that is a must-visit in Orlando, whether on a day trip or a week-long vacation. I hope that this quick guide to Winter Park, Florida helps you plan the best trip ever. If you think that I missed anything or have anything to add please leave us a comment below!

We hope that this article has inspired you to visit Winter Park, Florida. If you have any questions or advice to share with our readers, please leave these in the comments below.

Want to share your travel tips by guest writing for We Are Travel Girls? Please visit our Contribute Page for guidelines and to submit your article.

Join 8 million+ readers, get travel tips, event invites, trip discounts and more!

Read More About Florida

• 5 Fantastic Florida Kayak Escapes
• The Best Of Key West – Beyond Duval Street
• Dry Tortugas National Park: A Fortress In The Sea
• How To Have The Perfect Florida Keys Roadtrip
• The Best Things Central Florida Has To Offer

We Are Travel Girls Ambassador Daisy MacLellan Connect with Daisy Website | Instagram | Pinterest

Pin For Later

This article may contain affiliate links, if you purchase something using one of our links we may receive a commission. Please see our Disclosures f or more information.

You’ll Also Love

Leave a reply cancel reply.

Your email address will not be published. Required fields are marked *

Notify me of follow-up comments by email.

Notify me of new posts by email.

• Travel Girls Getaways
• DESTINATIONS
• TYPE OF TRAVEL
• TRAVEL RESOURCES
• AMBASSADOR PROGRAM
• TRAVEL GIRLS GIVING

Get Access To The Travel Resources Library

Subscribe to receive free access!

• Work With Us
• TESTIMONIALS
• DISCLOSURES
• TERMS OF SERVICE
• PRIVACY POLICY
• ACCESSIBILITY

COPYRIGHT © 2023 WE ARE TRAVEL GIRLS

Exclusive Member of Mediavine Travel

• Winter Park FL, 32789
• [email protected]

Your Guide to Winter Park

• January 21, 2017

Since When you travel to Winter Park, it feels like a “world” away from the tourist spin cycle that is international drive and the theme parks, it always surprises visitors that it’s just = minutes away drive from the world’s most popular theme parks.

Winter Park was originally developed for wealthy “snow birds”. They were seeking a quiet and comfortable place to live. These ‘snowbirds’ wanted to and escape the harsh winters. The city was originally named Lakeview. In 1881, two businessmen, Loring Chase and Oliver Chapman, decided they wanted a name to be more reflective of winter in a park. They renamed the city to Winter Park. To this day, the city still attracts a lot of winter visitors because of its comfortable weather, laid back lifestyle and countless unique places to visit.

There are so many reasons to fall in love with Winter Park. The town of Winter Park has been featured in a number of articles, movies, and TV shows.  National Geographic Traveler  magazine has named Winter Park one of the world’s top historic destinations. The nave noted “this gracious town manages to retain its reputation as an oasis within the rapid growth of Central Florida.” Winter Park’s small downtown has a commercial district with some interesting buildings filled with history and privately owned businesses. It also has a nice historic residential area. There is a clear sense that this is very much a place where everyday life occurs. Winter Park is not just a showpiece for tourists.

Winter Park’s vision statement really puts into perspective what the city is all about: Winter Park is the city of arts and culture, cherishing its traditional scale and charm while building a healthy and sustainable future for all generations. The town of Winter Park has done an amazing job at being able to provide activities for all to enjoy. When are you going to travel to Winter Park?

Winter Park Farmers’ Market

The Winter Park Farmers’ Market is a great way to start your weekend. It is held from 7am to 1pm every Saturday morning. The WP Farmer’s Market is held at the old train depot. It has been restored into a historical landmark. The train depot is located on the corner of W. New England Avenue and S. New York Avenue.

Since it’s in Winter Park, you can expect to find a few upscale choices that you would normally not find at more typical farmers’ markets, yet there is plenty that is affordable. The breakfast and lunch choices are something to definitely consider. Look for fresh crepes, pastries, and quiche. The local honey is a must. There is always a great garden selection. If you hang out until the early afternoon, you’ll find that a lot of the prices tend to go down.

There’s also an indoor space for vendors, which is great when it’s raining or if you want to cool down a bit. While you’re inside, the Winter Park Historical Museum which is open on Saturday from 9am until 1pm is located in the same building. Admission is free and exhibits give you a glimpse into the history of Winter Park.

Winter Park Boat Tour

Established in 1938, the fleet of six 18-passenger pontoons give you a tour through Winter Park’s chain of Lakes. It is a MUST SEE for all. Every tour is sure to impress with amazing views of nature. It also reveals the history of the luxurious private homes and estates along the tour. Keep an eye out for an occasional sunbathing alligator.

The dock is less than 5 minutes from Park Avenue and is located on the East end of Morse Boulevard on Lake Osceola.

Rollins College

The Rollins College 70-acre campus contains a range of amenities, including a theater for performing arts; the Cornell Campus Center; and the Alfond Sports Center.  Rollins College was founded in 1885. It is Florida’s oldest recognized college. Located on the banks of gorgeous Lake Virginia, it’s a great campus to take a stroll around. If you’d like a more intimate and detailed tour, contact the Office of Admission or visit this  link .

Charles Hosmer Morse Museum of American Art

The Charles Hosmer Morse Museum of American Art, opened in 1995. It houses the most extensive collection of works by American designer Louis Comfort Tiffany (1848–1933). The chapel interior was designed for the 1893 World’s Columbian Exposition in Chicago. See it at the Charles Hosmer Morse Museum of American Art. The museum showcases art and architectural elements from Tiffany’s Laurelton Hall. This was his Long Island Estate.

Highlights also include the recently restored Daffodil Terrace prize-winning leaded-glass windows, Tiffany lamps, and custom furnishings just to name a few. Visitors can also enjoy the exhibits of American art pottery, Arts and Crafts furnishings, and late 19th- and early 20th-century American graphics and paintings.

• Art and Culture , Museums , Travel

Share this post:

The Imperial Announces New Home On Park Avenue

Bazaar Botanica – Weird Artisan Market

Orlando To Install Speed Cameras In School Zones To Fight Speeding

Coro: A Culinary Symphony In Winter Park, Florida

Everything you need to know about disney world’s new lightning lane line-skipping pass, m’ama napoli: authentic italian bakery and deli now open in winter park.

Find the updates on everything in Winter Park and the Orlando area, right here. With constant updates from us; you, family, and friends can truly live the life that the wonderful city of Winter Park has to offer.

Park Ave Magazine is proud to be your local guide for the Winter Park and Central Florida areas.

Latest Posts

Submissions.

• Submit Writing
• Submit An Article
• Submit An Event
• Advertising

Copyright © 2024 Park Ave Magazine. All Rights Reserved. | Privacy Policy

• Skip to primary navigation
• Skip to main content
• Skip to primary sidebar
• Skip to footer

TravelAwaits

Our mission is to serve the 50+ traveler who's ready to cross a few items off their bucket list.

6 Amazing Things To Do In Beautiful Winter Park, Florida

• Destinations
• United States

Located just seven miles north of the City of Orlando in Orange County, Winter Park’s 30,000 residents enjoy abundant outdoor spaces, a decadent Saturday morning farmer’s market, golf courses, and more museums than you would ever expect to see in such a small area. Created by several wealthy industrialists as their winter haven in the late 19th and 20th centuries, boating, museums, shopping on Park Avenue, and great food make it as delightful today as it was then.

I attended a press trip that included Winter Park. All the opinions herein are my own.

1. Scenic Boat Tour

The Scenic Boat Tour is a must-do and the perfect introduction to Winter Park. It is the oldest, continuously running attraction in the state of Florida since 1938! They operate seven days a week, 364 days a year (not Christmas). Peppered with jokes, facts, and wry asides, Skipper Don Brown’s a treasure trove of information along this gorgeous tour.

The Winter Park chain of lakes is connected by navigable canals created by Charles Mizell of timber fame to ship his product between six lakes (Maitland, Minnehaha, Mizell, Nina, Osceola, Virginia) in the mid-1800s.

The pontoon boats can’t have a roof or cover because the water levels on the lakes can be quite high during the wet season and there isn’t enough clearance for the boats to pass under bridges that dot the canals. Don’t worry, the lake view of all the historic homes make it well worth the trip with people kayaking around the pontoons.

Before you move too far along in our journey, though, it’s time for the first section of the historic shoreline to receive a shout-out. On the right side of the lake once stood the Old Seminole Hotel, the grandest hotel in the state of Florida. In 1886, maybe even the United States. It had 250 hotel rooms and a four-story tall observation tower from which you could see both Lake Osceola and Lake Virginia. Most impressive was its front porch, stretching 600 feet (that’s two football fields). Host to Presidents Grover Cleveland and Benjamin Harrison, many said that Rollins College and the Old Seminole Hotel brought “luxury to the edge of the Florida frontier.”

Sadly, the hotel caught fire in 1902 and burned to the ground.

Along the Scenic Boat Tour route, identify the “Resurrection Fern” and the “Dinky Dock,” an ecologically protected cypress with several homes designed and built by the famous architect, James Gamble Rogers.

2. The Charles Hosmer Morse Museum Of American Art

The Charles Hosmer Morse Museum was created by his granddaughter Jeannette Genius McKean and her husband Hugh McKean who had completed an internship with Louis Comfort Tiffany glass earlier in his life. First housed on the Rollins College campus, the collection outgrew that space, especially after the couple rescued as much as possible from Tiffany’s Laurelton Hall, Long Island, New York home that collapsed during a fire. It was the quick work of Jeannette and Hugh that saved so many panels of this precious work .

Along the tour, you’ll learn how many different mediums Tiffany found to work with. There are his lamps, of course, but also jewelry and furniture, the most astounding windows… explore how the light changes based on your position.

3. Albin Polasek Museum And Sculpture Gardens

Albin Polasek Museum and Sculpture Gardens , with over 400 bronze pieces, visible from the Scenic Boat Tour, remains a popular wedding venue and was donated by the artist’s wife following the death of this incredible Czech American talent in 1962.

However, the story of this museum and its foundation goes further still. When the Capen House was sold, the Polasek offered a safe haven for the original home. The new owners of the land the Capen House stood upon paid for the house to be split in two (called Fred and Ginger after the famous American dance team, Fred Astaire and Ginger Rogers), rolled down the hill, and floated across Lake Osceola to its current location. It took 45 minutes for the first half, according to our skipper, and 15 minutes for the second. Check out the YouTube video from 2010 where a drone covered the event. Movement across the lake starts at 1 minute and 42 seconds. 

Also found in Winter Park is the Rollins Museum of Art, the Winter Park History Museum, Casa Feliz Historic Home Museum, and Hannibal Square Heritage Center, with art galleries regularly hosting berry special events. If you’re interested in classes or summer art camp, check out the Crealde School of Art.

4. Kraft Azalea Gardens

While many visitors know to go to Mead Botanical Gardens, one of Winter Park’s best but little-known attractions remains Kraft Azalea Gardens . Popular for weddings, marriage proposals, and birthdays, it’s a magical place.

Located on Lake Maitland’s shores, this 5-acre public garden is free to enter and open year-round from 8 a.m. to sunset, with a boat dock, benches, and eight more acres of park to explore outside the garden. Relax at The Exedra, reminiscent of Golden Gate Park ’s Spreckels Temple of Music, wander the great egret rookery, or visit the northernmost Banyan Tree in the state of Florida.

5. Saturday Morning Farmers Market

Advertised as the “Number one produce and plant market in Central Florida,” Winter Park’s Farmers Market contains the city’s central park and lives up to the hype with a lovely, festive gathering place with vendors and shoppers reveling in the fresh, colorful produce, assortment of plants, baked goods, artisanal crafts, and other offerings. The City of Winter Park Sidewalk Art Festival is held in this same location each year. Details can be found here .

The train station stops nearby. They are still serviced by Amtrak.

6. Winter Park Shopping

Rifle paper company.

Winter Park’s Park Avenue provides ten tree-canopied blocks where you can wander around the 140 specialty shops, cafés, boutiques, and coffee shops. If you love stationery, you’ll want to stop at  Rifle Paper Company .

Peterbrooke Chocolatier

Interested in gourmet chocolate? Peterbrooke Chocolatier’s assortment of chocolate delicacies will tantalize your taste buds.   

The Impeccable Pig  

Need to find a chic outfit or trendy accessories? Check out The Impeccable Pig .

The Wine Room On Park Avenue

If you’re looking for a decadent restaurant experience with a special wine, cheese, and charcuterie (or to take as a gift to those at home), you’ll want to check out The Wine Room .

Winter Park Restaurants

As with most wealthy towns, Winter Park’s restaurants provide an embarrassment of riches. The sheer abundance of food found from The Glass Knife to the surprisingly good “college food” at Rollins College to the James Beard nominated chefs James and Julie Petrakis of The Ravenous Pig with special attention to great locations for vegans and husbands in need of “daycare,” there’s something for everyone in Winter Park.

The Glass Knife Cakes And Café

Executive Chef Kristy Carlucci and General Manager Bianca Hinksman recommend reservations at The Glass Knife if you’d like to eat on the porch on a typically busy day.  

Displays of season-specific items atop the glass display cases filled with decadent croissants, pastries, and cakes. Menus for brunch and beverages hang above rows of freshly made doughnuts.

Look closely at the long, butcher block table beneath the rectangular chandelier base and dropped pendant lights that line the entire 12-seat table. Therein lie several eponymous glass knives in multiple colors. The imperfections make them stunning.

Rollins College

Two places to eat on Rollins College’s Campus , the Boat House and the Student Cafeteria, Skillman Dining Hall, bring you to campus but you’ll stay to walk around and see why it highly ranks each year on the “ Most Beautiful College Campus ” list.

The college’s cafeteria is spacious, light, and inviting with some of the best views on campus across an Olympic size pool over Lake Virginia.

Dave’s Boathouse, a Star-K Kosher certified facility offers a dark wood finish large bar area as you enter from the lakeside with cozy dining and large tables to fit your party size.

If you’d like to stay on campus, check out The Alfond Inn . 

Ethos Vegan Kitchen

Enter Ethos ’ fun, festive atmosphere to a wide display of artwork, from the playful to the profound, you can choose to be seated or place a takeaway order behind the hostess station. You’ll be impressed with the “common” names in this vegan restaurant from sausage rolls and “chickun” or pork. Even bay cakes, their rendition of crab cakes, move quickly across the restaurant as happy plant-based diners eat their fill.

Fiddler’s Green Irish Pub And Eatery

Wives, take notice. Fiddler’s Green Irish Pub on Fairbanks Avenue declares itself:

“Winter Park’s oldest husband daycare center. If you need time for yourself, leave your husband with us. Packages, 1, 2, 3 pints available.”

It’s listed right under the Jameson sign, so it must be true.

Their bill of fare contains only two pages but is jam-packed with flavor and fun with plenty of Irish dishes and American favorites. Try the Irish egg rolls, boxty potato pancakes, shepherd’s pie, Irish stew, or the favored corned beef and cabbage.

The Ravenous Pig

James Beard nominated chefs James and Julie Petrakis have spent 16 years refining the customer experience at The Ravenous Pig . If you’re ready for a Florida twist, try the s’mores French toast (a thick, dark, brioche served with maple syrup, burnished marshmallow, and a dark chocolate mousse), pimento cheese fries, or fried chicken cordon bleu.

For a real treat, order the longboard of charcuterie that crosses the entire five-seat round-top table. Our server introduced us:

“Here we have soppressata, Saville Road cheddar, tête de cochon, and the lomo, the Toscano, and the camembert accompanied by a spicy IPA mustard as well as date jam, lamash, and salted walnuts.”

It’s impressive — a wine and cheese connoisseur’s dream.

Downtown Winter Park is close enough to downtown Orlando to make it an excellent day trip.

For more information on traveling to Florida , check out these articles:

• 17 Most Popular Florida Vacation Rentals (2022)
• 16 Florida Beach Towns Our Readers Love (2022)
• 8 Amazing Things To Do In Beautiful Tallahassee, Florida

Gail Clifford, MD, a physician for 30 years, has traveled to five continents and has visited all 50 United States. An avid traveler, she happily goes on new adventures, especially for birthdays. Multi-generational travel remains a treasured pastime. She currently divides her time between Ireland and the U.S. You can experience more from Gail on her site ABLE Travel & Photo .

Things To Do

• Outdoor Activities
• Route 66 in Illinois
• Arts & Culture
• Attractions
• Food & Drink
• Lincoln Historic Sites
• Illinois Scenic Byways
• Festivals & Events

Places To Go in Illinois

• Chicago & Beyond
• Great Rivers Country
• Land of Lincoln
• Trails to Adventure

Plan Your Trip

• Travel Inspiration
• Road Trip Itineraries
• Illinois Made
• Places to Stay
• Seasonal Adventures
• Exploring Illinois with Electric Vehicles
• Getting Here & Getting Around
• Maps & Visitor Guides

Accessibility in Illinois

• Tourism Industry
• Like us on Facebook
• Follow us on Instagram
• Check our Pinterest
• Follow us on TikTok
• Follow us on LinkedIn
• Subscribe to our channel on YouTube

Sep 01, 2016 • Regional Getaways

Ice, snow; wrap up and glide into the holiday season with open air ice skating rinks, lights festivals, skiing and snow sculpting.

Maggie daley park skating ribbon.

Forego the typical rink roundabout for  Maggie Daley Park’s Skating Ribbon, overlooking Lake Shore Drive in downtown Chicago. With the city skyline as its backdrop, this stretch of ice weaves its way through a beautifully manicured landscape. Stop to take in the scenery (as well as a piping cup of hot chocolate) and revel in this unique urban skating adventure. 

Chicago Wolves Skating Rink at Brookfield Zoo

Glide through the holidays at   Brookfield Zoo's   Skating Rink! Admission is $7 for all skaters and  a limited number of skates are available for a $5 rental fee. The rink is not made of ice, but of a synthetic material known as Glice® – so no water or electricity is required for operation. Brookfield Zoo is one of only three zoos in the country to install a Glice® rink!

Illinois Snow Sculpting Competition

Rockford’s  Sinnissippi Park  is home to Illinois’ premier snow sculpting competition, which began as a passion project for a local businessman in 1987. Today, the  Illinois Snow Sculpting Competition  hosts state and high school teams from across Illinois that face off for the chance to represent their crews in the national finals. More than 30,000 fans show up to cheer on their favorites every January.

Starved Rock State Park Winter Sports

For winter hiking  Starved Rock State Park in Utica is a popular destination for the cold-weather outdoor enthusiast. Imagine the crunch of newly fallen snow as you trek your way through the pristine woods and the majesty of the frozen waterfalls that mark this stunning terrain, which was formed by glacial meltwater eons ago.

Chestnut Mountain Resort Nighttime Skiing

Historic Galena is home to  Chestnut Mountain Resort , where 3,500 feet of fresh powder awaits all levels of skiers and snowboarders. The real magic begins once the sun goes down and the snow literally glows during the weekly  Fantastic Friday, when the slopes stay open until midnight. Illuminated ski runs light up the night during the months of January and February.

You might also like...

Winter activities in illinois, winter adventures in illinois, winter in illinois.

Save for later

Share this story

Share your Moments

#enjoyillinois, subscribe to our newsletter.

Get inspired by top travel stories, gain access to exclusive promotions and contests, and discover even more reasons to #EnjoyIllinois.