20 Best Things to Do in Winter Park, FL

Winter Park, FL
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Located just north of bustling Orlando, Winter Park takes importance in its culture and heritage.

With its wide array of museums and historic destinations, tourists flock here to learn more about the city and experience its culture firsthand.

While small, Winter Park boasts many interesting places that can make your trip here both fun and enjoyable.

Building your itinerary for a visit?

Here are some of the best things to do in Winter Park, Florida:

Explore Downtown Winter Park

Downtown in Winter Park
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Visiting a city’s downtown district has always been a good way to know more about the place you are visiting.

The same goes for Winter Park.

At the city's heart, you can find Park Avenue, a fine place for shopping and dining.

Downtown in Winter Park
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Many charming cafes, amazing eateries, and boutiques offering interesting knickknacks line the sidewalk of this avenue.

Here you can find delicious food and interesting souvenirs that you can get to remember your trip here.

Spend a Date Night at Hannibal’s Lounge

Traveling through Winter Park with your significant other?

Well, you may discover that this city can also be a romantic one.

Many consider Hannibal’s Lounge as one of the best spots for a date night in the city.

Located at the city’s West New England Avenue, many locals know this restaurant for its scrumptious French dishes.

However, this restaurant remains versatile as it also offers a myriad of other food options, such as delicious steaks, refreshing cocktails, and rustic desserts.

Hannibal’s Lounge continues to provide good service and great food to those who visit it.

Catch a Film Screening at Central Park

Fountain at Central Park in Winter Park, FL
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Have you ever watched a movie while feeling a cool breeze outdoors?

Enzian, in collaboration with the city of Winter Park, offers this experience to locals and tourists alike.

Every second Thursday night of a month, they offer screenings of interesting films at Central Park.

After the sun sets and when it gets dark, people settle on picnic blankets on the park's grounds to watch a movie.

While waiting for the screening, why not take a stroll through this beautiful park, too?

This 11-acre part continues to be a great place for people to hang out and relax.

Find Vintage Comics at a Comic Shop

For lovers of comic books, here’s an interesting destination.

While it may seem like an unusual addition to your Winter Park itinerary, do consider checking out A Comic Shop.

Here, you can shop for hard-to-find, obscure comic book titles, and issues.

If you’re on the lookout for that one rare title or issue, consider stopping by at this shop, as you may finally find it here.

The shop also hosts events that you can check out if you’re around.

Take a Nice Walk Through Kraft Azalea Gardens

Great Egret at Kraft Azalea Gardens
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You can find a lot of amazing parks and gardens around Winter Park.

Just a few minutes' drive from Park Avenue, the 11-acre Kraft Azalea Gardens offers another respite for locals and tourists wandering across the city every day.

Lake on Kraft Azalea Gardens
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Here, you can witness amazing lake views as it borders the charming Lake Maitland.

If you need a breather, or if you and your travel companions want to go on a picnic, consider Kraft Azalea Gardens as the place to visit.

Spend a Night at the Alfond Inn

Gorgeous boutique hotels enhance one’s stay at a destination, and in Winter Park, one such place is the Alfond Inn.

As an extension of the Cornell Museum of Fine Arts, this hotel's designer built it to feature many beautiful artworks featured all around the hotel.

Apart from gorgeous luxury rooms and awe-inspiring art, the inn also features the famous Hamilton’s Kitchen, where you can get sumptuous meals while staying here.

Elevate your visit to Winter Park by checking out this hotel.

Appreciate Nature at Mead Botanical Gardens

Stream in Mead Botanical Gardens
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If you want to discover flora and fauna and appreciate what nature can offer, then you should consider visiting Mead Botanical Gardens.

While strolling through its paths, you can find many plants from around the world - from exotic orchids and night-blooming cacti to local long-leaf pines.

Owl in Mead Botanical Gardens
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Animals such as raccoons, bats, and even alligators can also be found here.

You can also choose to relax under one of its pavilions under the shade of towering oak trees.

Hike or Bike Through the Cady Way Trail

If you like to stay active while appreciating the great outdoors, consider trekking through the Cady Way Trail.

Locals and tourists alike say they love moving through this 6.5-mile trail, as it offers historical scenes with great outdoor views.

This trail was formed along the East Florida & Atlantic Railroad’s abandoned roadbed, and it goes through Baldwin Park.

It also passes through some of the gorgeous homes you can find in Winter Park.

The Cady Way Trail forms a part of a network of other multi-use trails that you should also consider checking out.

It’s definitely worth checking out if you want to explore Winter Park and its neighboring areas.

Go Sailing Across Lake Virginia

Lake Virginia
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Lake Virginia remains one of the city’s most popular attractions, and for a good reason.

You can find a nice view of gorgeous mansions and Rollins College along its banks.

Scenic boat tours in Lake Virginia
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Consider experiencing this by going on a scenic boat tour across the lake.

Apart from boating, tourists can also take part in water sports in Lake Virginia.

When you come here, definitely try out stand-up paddleboarding, kayaking, and even water-skiing.

Try the Seafood at Mitchell’s Fish Market

Hungry for some great seafood?

Head on over to Mitchell’s fish market, where you can try out some of the best and freshest seafood around.

Here, you can try out some of the best seafood, not just locally but also from different parts of the world.

They offer anything from lobster tails and grilled shrimps to Atlantic cod and more.

While this place primarily features seafood, it also caters to those who fancy other protein as they have chicken and beef dishes available as well.

With a great deal for happy hour, delicious dishes, and great service, you should definitely consider checking this place out.

Go Shopping at the Farmer’s Market

Farmer’s market in Winter Park
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If you want to shop for local produce, check out the local farmer’s market.

Set up in an old, restored train station, you can shop here for local products that you may want to try out.

Occasional expos and events take place at this venue.

The market usually opens from 7 am to 1 pm, so consider waking up early if you want to get the freshest produce from the stalls here.

Play Golf at the Local Course

If you want to spend a relaxing day in Winter Park, consider playing golf at the local golf course.

Known as Central Florida’s second-oldest golf club, the Winter Park Country had first opened its doors in 1914.

It hosted many players who have wanted to enjoy the sport ever since then.

Going through the downtown district, this place provides a fun and great challenge to golfers of every proficiency.

Have fun playing this awesome recreational sport when you’re in the area by visiting the local Winter Park golf course.

Learn About the City’s History at Winter Park Museum

Winter Park history Museum
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Getting to know Winter Park goes beyond looking around.

With all the beautiful cultural venues and art parks, you may wonder how this city became a champion of the arts.

One way to find out is by learning about the city at the Winter Park Museum.

Situated on New England Avenue, this museum houses many interesting artifacts, partnered with many historical facts that you can learn about.

It also hosts many different exhibits where you can learn more about how the residents of Winter Park lived throughout history.

Appreciate Awe-inspiring Artworks at Albin Polasek Museum and Sculpture Gardens

Albin Polasek Museum and Sculpture Garden
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The city of Winter Park houses many interesting museums you can visit, and the Albin Polasek Museum and Sculpture Garden is a popular choice among tourists.

This museum houses sculptures made by the late Czech sculpture featured on the museum’s name - Albin Polasek.

A painter painting at Albin Polasek Museum and Sculpture Garden
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Looking to start a new art collection?

Exhibits here also feature art made by local and international artists, some of which you can purchase.

If you visit Winter Park, consider adding this museum to your itinerary.

Catch a Performance at the Winter Park Playhouse

Do you love watching musicals?

While visiting the city, don’t forget to check out performances at the Winter Park Playhouse.

Serving as Central Florida’s only professional musical theater, you can check this place out if you want to watch great musical comedies, cabarets, and revues.

The venue features shows all year round, so you would definitely catch one when you go here.

It’s a good place to find great entertainment while visiting Winter Park.

Be Amazed by the Exhibits at the Charles Hosmer Morse Museum of American Art

Charles Hosmer Morse Museum of American Art
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Many consider the Charles Hosmer Morse Museum of American Art as another popular and interesting destination to visit while in the city.

Similar to many other art museums in the area, this one features many amazing works from local artists.

Entry to Charles Hosmer Morse Museum of American Art
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However, its extensive collection of works by Louis Comfort Tiffany serves as its claim to fame.

Some of the Tiffany works here include items ranging from pottery, jewelry, and lamps, to the entire chapel interior that Tiffany made for the World’s Columbian Exposition held in Chicago back in 1893.

Tourists can visit the museum from Thursday to Sunday, so don’t miss out if you visit the area.

Discover Local African-American History at Hannibal Square Heritage Center

While small, Winter Park boasts a rich history that formed its identity as a city.

If you want to know more about it, do visit the Hannibal Square Heritage Center.

This place has photos and interesting information about West Winter Park.

It also houses information about the Hannibal Square timeline, educating its visitors about the events significant to the African-American community throughout history.

Hannibal Square served as one of the first places in the country where African-Americans could purchase their own property.

The city’s history has many significant events, and you can learn some of them by visiting this.

Visit the Cornell Fine Arts Museum

Cornel Fine Arts Museum
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Art thrives in Winter Park, and The Cornel Fine Arts Museum hosts a myriad of amazing art collections that amaze everyone.

Located within the campus of Rollins College, the museum boasts a gallery made up of over 5,000 collections.

It features items ranging from drawings and paintings to prints and photographs.

Here, you can choose to walk around and discover artworks on your own or avail of different guided tours if you want to know more about the museum’s collections.

Appreciate Classical Music With the Bach Festival Society

Many know German composer Johannes Sebastian Bach as one of the most prolific musicians in history.

Paying homage to his great works, the Bach Festival Society entertains both local and international audiences with impressive performances of this famous composer’s pieces.

The Bach Festival Society is known to be the United State’s third-oldest Back Festival.

It also serves as the oldest performing arts group in Central Florida.

Volunteers who have auditioned for the group form the core of this arts organization.

More than 160 singers coming from vastly different backgrounds make up the choir, all of them share a love for amazing musical pieces.

Explore Casa Feliz Historic Home Museum

Casa Feliz House museum
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Many people interested in local history almost missed out on this destination.

Prior to becoming a museum, Casa Feliz had almost been demolished.

This destination is a Spanish Farmhouse built according to the design of James Gamble Rogers II, a famous architect.

It features gorgeous furnishings, including Spanish roof tiles and bricks.

This unique piece of architecture also has a bell tower, a balcony and courtyard, and even a turret.

The house also has a museum, which showcases what everything looked like in a Spanish house back in the 1800s.

Final Thoughts

Winter Park values its history, culture, and heritage, as proven by the many museums it houses.

For lovers of history and art, visiting this place city should be a must.