14 Best Things to Do in Winter Park (FL)

Located in central Florida’s Orange County within the Orlando, Kissimmee, Sanford Metropolitan area, Winter Park is a city of just more than 27,000 residents. It’s known as a winter destination for Midwestern snowbirds, who prefer its abundant sun and mild climate to months of freezing temperatures and grey skies.

The land on which the city now resides was first settled in the early 1880s, and the town was officially incorporated shortly after that.

The area is a favorite for active and outdoorsy types, who appreciate the abundant parks, golf courses, and cobbled streets in the historic downtown.

Below are 14 things to do in Winter Park.

1. Charles Hosmer Morse Museum of American Art

Charles Hosmer Morse Museum Of American Art

Located on North Park Avenue in Winter Park, the Charles Hosmer Morse Museum of American Art is home to one of the world’s most complete collections of Louis Comfort Tiffany’s creations, including leaded glass windows, paintings, pottery, and the lampshades for which he is most well-known.

Many of the items on display were originally located at Tiffany’s Long Island home and studio, and the museum is a unique mix of art, culture, and history that make it well worth a visit.

The cost of admission is inexpensive, and it’s conveniently located close to other area attractions you’ll likely want to visit.

2. Central Park

Central Park, Winter Park

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Central Park, Winter Park

Winter Park’s Central Park is one of the city’s recreation jewels because it hosts a variety of events and performances throughout the year. At other times, it’s just a pleasant place for a stroll or to relax with a good book or a good friend.

The park offers guests a nice mix of natural areas and shops, and there’s a popular rose garden at the south end that’s particularly beautiful during the spring bloom.

Check their website to see what’s on the schedule for when you’ll be visiting, and remember that most events take place in the cooler months outside of summer.

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3. Lake Virginia

Lake Virginia, Winter Park

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Lake Virginia, Winter Park

Like much of central Florida, the land around Winter Park is dotted with lakes of varying shapes and sizes; they offer locals and visitors a variety of recreation options, including swimming, sunbathing, fishing, and boating.

Lake Virginia is one of the city’s most scenic attractions, and many visitors choose to explore it by kayak or pontoon boot, which can be rented inexpensively.

There’s also a full-service guided boat tour option that’s perfect for those who’d rather not expend energy or break a sweat. There are a number of dining options nearby that are perfect places to relax over a meal and a drink after a long day in the sun.

4. Albin Polasek Museum & Sculpture Gardens

Albin Polasek Museum & Sculpture Gardens

Located on Osceola Avenue in Winter Park, the Albin Polasek Museum and Sculpture Gardens predominately exhibit the works of a famous Czech sculptor, who spent much of his life in Florida.

Most guests find his works brilliant and thought-provoking, and though the artist has been dead for quite a while, what was once his home and studio has been open to the public for more than 50 years.

Admission is relatively inexpensive and includes a guided tour; you’ll want to take some time to explore the butterfly and water gardens on your own before heading off to new adventures.

5. Hannibals lounge & Chez Vincent

Hannibals Lounge & Chez Vincent

Located on West New England Avenue in downtown Winter Park, Hannibal’s on the Square and its next-door neighbor Chez Vincent share a wall, an owner, and a kitchen, and are two of the trendiest culinary destinations in the area.

Though it’s known for the French food, the restaurant features a variety of other options – from steaks and seafood to world-class cocktails and homemade desserts.

Hannibal’s probably isn’t the best bet for a family of six traveling on a budget, but for a unique and classy date night, anniversary, or other special occasion, you probably won’t find a more appealing or memorable venue.

6. Hannibal Square Heritage Center

Hannibal Square Heritage Center

Though Winter Park is on the small side, therein lies much of its charm; what it lacks in size it more than makes up for with its history and quaintness.

Hannibal Square Heritage Center is a community museum dedicated to preserving and promoting the area’s culture and history. It includes several exhibits containing photographs, first-hand accounts, and other memorabilia related to the city’s founding and development.

Many guests find the items related to African Americans to be among the most interesting and poignant, and there are many pieces of artwork created by black Americans as well.

7. A Comic Shop

A Comic Shop

For hardcore comic book aficionados visiting the Winter Park area, there’s really only one destination; it’s especially popular for truly offbeat and obscure comics that aren’t so easy to come by these days.

A Comic Shop is located on Semoran Boulevard in Winter Park. In addition to its eclectic inventory and attentive staff, it features a dedicated area that hosts all kinds of quirky events aimed at gamers, geeks, and artsy types.

The best way to get an idea of their products, services, and schedule of events is to connect with them on Facebook and check-in regularly.

8. Mead Botanical Garden

Mead Botanical Garden

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Mead Botanical Garden

No matter where your travels take you within the borders of the Sunshine State, chances are you won’t be far from a botanical garden or two. With such an abundance of sun, rain, and balmy weather, it’s no wonder.

Located on South Deming Drive in Winter Park, Mead Botanical Garden is known for its plethora of plants, trees, and flowers from all over the world. Though it’s beautiful no matter when you visit, most guests rave about the annual orchid bloom that takes place in the spring.

The gardens easily walkable trails lead through a variety of natural environments. In addition to their flora, the garden is home to lots of animals too.

9. Austin’s Coffee

Austin’s Coffee

For hopelessly addicted caffeine junkies, getting their morning or afternoon fix can be the highlight of their day – whether they’ve just visited the Eifel Tower with a supermodel or spent the afternoon shopping for garage paint in Cleveland.

Austin’s Coffee is located on West Fairbanks Avenue and is known for its professionally prepared drinks, including all the old standbys like cappuccinos and espressos. Unlike most of their competitors, they offer an extensive craft beer menu as well.

It’s a contemporary and laid-back environment that’s a favorite of those who work from their computers but are fed up with the office. They offer a full menu that runs from fresh baked goods and sandwiches to soups and vegan offerings.

10. Winter Park Farmers’ Market

Winter Park Farmers’ Market

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Winter Park Farmers’ Market

Held in the historic train depot on West New England Avenue, the Winter Park Farmers’ Market is said to be central Florida’s number one farmers’ market. Though that’s a claim that’s yet to be substantiated, most visitors agree that it offers an impressive selection of items – and that it’s just downright fun too.

The market happens on Saturdays from 7 AM until 1 PM. In addition to its large variety of fresh, seasonal, and organic produce, it offers guests lots more, like flowers and plants, health and body products, and prepared items like Florida honey, baked goods, and fresh juices.

Check out the recommended hotels in Winter Park, Florida (FL)

11. Scenic Boat Tours

Scenic Boat Tours, Winter Park

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Scenic Boat Tours, Winter Park

Central Florida is full of lakes, and many of them are surrounded by parks and access points, making them popular with energy-filled kayakers and paddle-boarders. But for those who’d rather relax in the shade, enjoy professional narration, and let a machine take care of propulsion, a few hours spent on a Scenic Boat Tours excursion is a great idea

The tours focus on the history, development, and natural attractions of the area, generally last about an hour and hit many lakes, canals, and neighborhoods.

Bring your camera, because gators, wading birds, and amazing views are common.

12. Winter Park Sidewalk Art Festival

Winter Park Sidewalk Art Festival

Drawing hundreds of thousands of artists and art lovers from all over the country every year, the Winter Park Sidewalk Art Festival is one of the most revered events of its kind and is held in Central Park.

The festival includes traditional works including paintings, sculpture, and a variety of contemporary mixed-media as well. It’s the perfect destination for those looking to pick up a one-of-a-kind piece, and for artists who struggle with inspiration.

The festival is held in March annually when the Winter Park weather is perfect. There are plenty of food, drink, and entertainment options as well.

13. Winter Park Golf Course

Winter Park Golf Course

With a history that dates back more than a century, the Winter Park Golf Course is one of the oldest in the area. Though much of it is original, it’s undergone a massive renovation recently that’s brought it up to modern specs.

Featuring new and improved greens, fairways, and sand and water hazards, it was recently voted one of the ten best short courses in the nation by a well-known golf magazine.

The course is only nine holes and plays about 2,500 yards, which makes it the perfect destination for those who’ve got busy schedules with only a few hours to spare.

14. Wekiwa Springs State Park

Wekiwa Springs State Park

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Wekiwa Springs State Park

Though it’s not the closest attraction to Winter Park, Wekiwa Springs State Park is still an easy drive, and is conveniently located just off Interstate 4.

The park contains the headwaters of the Wekiva River and is most well-known for the cool waters that continually bubble to the surface of its natural pools, making it an especially popular destination when the Florida heat is bordering on oppressive.

Inexpensive to visit, there are a variety of trails leading through varied natural environments. Its myriad of navigable waterways are popular with kayakers, bird watchers, and anglers.

Where to stay: Best Hotels in Winter Park, Florida (FL)
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14 Best Things to Do in Winter Park (FL):

Lake Virginia, Winter Park