13 Best Things To Do In Winter Park, FL - Updated 2021

1. Enjoy the beautiful Kraft Azalea Garden

This public park in Alabama Drive is quite dreamy! It sits beside the serenely beautiful Lake Maitland, filled with thick cypress trees that stand ever so stately and striking. Imagine landscaped gardens with wooded pathways - the summer sun beaming brightly and the sweet music of the flowing lake waters in the background. Without a doubt, Kraft Azalea Garden is one of the places to get married in Winter Park.

Kraft Azalea Garden

Address: 1365 Alabama Dr, Winter Park, FL 32789, United States

Opening hours: 8am - 7pm (daily)

2. Explore local history at Winter Park History Museum

Small but loaded with fun historical facts and artifacts - that’s how you sweetly describe the one-room Winter Park History Museum on New England Avenue. If you’re curious about how the hospitality industry looked like in Winter Park pre-millennium, check out its present exhibit (as of this writing) of old hotels and motels thoughtfully put together. In the past years, Winter Park History Museum has hosted a long list of eye-catching educational events and exhibits, including 2014’s “Whistle in the Distance: The Trains of Winter Park” and the pre-2010’s “Gardens of Winter Park.” Check out its website for a sneak peek.

Winter Park History Museum

Address: 200 W New England Ave, Winter Park, FL 32789, United States

Website: Winter Park History Museumn

Opening hours: Tue - Sat: 11am - 2pm (closed on Sun & Mon)

3. Admire the exhibits at The Charles Hosmer Morse Museum of American Art

This 1942 museum holds an extensive collection of renowned art nouveau artist Louis Comfort Tiffany. Your eyes will have a grand feast, exploring the different elegant art pieces on display - jewelry, stained glass, paintings, vases, potteries, and more. While the museum maintains a varied selection of art nouveau designs, Tiffany, who is best known for his decorative stained glassworks, remains the focal artist at the present. Here, you will find his famous Madonna and Child chapel window, designed for the 1893 World’s Columbian Exposition. The museum also runs a shop where you can buy souvenirs. If you find anything you like - an exquisite necklace or a sophisticated lamp perhaps - buy it as a gift for yourself.

The Charles Hosmer Morse Museum of American Art

Address: 445 N Park Ave, Winter Park, FL 32789, United States

Website: The Charles Hosmer Morse Museum of American Art

Opening hours: Tue - Sat: 10am - 3pm (closed on Mon & Sun)

4. Spend a day at Downtown Winter Park

Downtown Winter Park is a dining and shopping district that exudes an irresistible charming vibe. Unlike your modern-day commercial centers, here is a Park Avenue sidewalk full of local restaurants, cozy cafes and patisseries, and colorful boutiques that altogether create a warm and relaxed atmosphere. Around the area, you will find a farmer’s market, your go-to place for fresh produce and homemade milk, and a small park, where you can take a short walk after coffee. If you’re new in town and running out of ideas for places to dine, drive or take a train to Downtown Winter Park, where dining and shopping choices are aplenty.

Downtown Winter Park

Address: 110 N Park Ave, Winter Park, FL 32789, United States

Opening hours: 9am - 10pm (daily)

5. Be inspired by Albin Polasek and his collection at Albin Polasek Museum & Sculpture Gardens

The Polasek conserves the American representational sculptures created by the late Czech sculptor, Albin Polasek and also exhibits works of regional and international artists. You can also buy exhibit pieces by local artists in the gallery. The sculptures are both amazing and brilliant according to reviewers. The museum is actually a Mediterranean-style retirement home and studio of Polasek, which he opened to the public in 1961. The admission fee is reasonable and you will be guided by a knowledgeable tour guide without having to pay extra. Overlooking Lake Osceola, the view is splendid, where you can admire the statues at the same time. After visiting the museum, you can wonder around the butterfly garden and water garden outside with Polasek’s works everywhere.

The Polasek is free of admission for a week in April each year, which is during the annual Winter Park Paint Out hosted by the museum, where 25 artists create their works publicly on the streets of Winter Park. Once their works are done, they will be showcased in the gallery’s ‘Wet Room’ and available for sale to benefit the museum.

Albin Polasek Museum & Sculpture Gardens

Address: 633 Osceola Ave, Winter Park, FL 32789-4429

Website: Albin Polasek Museum & Sculpture Gardens

6. Hop onto a boat and enjoy the view of Lake Virginia

Lake Virginia has a beautiful view of well-manicured mansions and Rollins College on its coastline. Discover the lake anyway you want. Explore the lake with your own boat, kayak or pontoon boat. You can also take the option of following the Winter Park Scenic Boat Tour. The tour is lead by a funny and friendly guide who will explain to you the interesting facts of Lake Virginia and the multi-million dollar and historical homes around the lake. Other than that, there are also kayaks and stand-up paddleboards available for rent. Tubing and water-skiing are also allowed on the lake. Bring along your binoculars if you want to get a closer look at the properties.

Lake Virginia

Address: Lake Virginia, Winter Park, FL 32789

7. Get a taste of the freshest seafood from Mitchell's Fish Market

Editor's Note: Photo taken from the establishment's official social account

Mitchell’s Fish Market gets the freshest seafood from different coastlines in the world like the Atlantic, Pacific and Gulf of Mexico. Their food ranges from lobster tail, planked salmon, Atlantic cod, grilled shrimp and more. Their food is​ fresh without any canned products or artificial tastes. If you are not a fan of seafood, there is also beef and chicken available. During happy hour, food from 4 USD to 7 USD and cocktails are served. The staffs are attentive and the food is mouth-watering, definitely worth your money!

Mitchell's Fish Market

Address: 460 N. Orlando Ave, Suite 122, Winter Park, FL

Website: Mitchell’s Fish Market

8. Take a stroll or cycle through Mead Garden

Editor's Note: Photo taken from the establishment's official social account

Besides being a great wedding venue, Mead Garden is also best for having a picnic or grill at the pavilions under the large oaks, take a stroll or ride a bike while enjoying nature. Plants from all around the world like orchids, night-blooming cacti that only bloom once a year, cypress trees, caladiums and begonias can be found in the garden, as well as native wetland and upland species like longleaf pines. Be patient and spot raccoons, squirrels, bats, snakes, alligators and different other faunas in the gardens. Catch the blooming seasons of certain plants such as cool-colored caladiums, which show their colors during summer, and the tea camillia blooms in November with a sweet fragrance.

Mead Garden

Address: 1300 S Denning Dr, Winter Park, FL 32789-5636

Website: Mead Garden

9. Understanding the history of African Americans at Hannibal Square Heritage Center

Editor's Note: Photo taken from the establishment's official social account

Winter Park is a small town packed with rich history, and that, you will realize while visiting Hannibal Square Heritage Center. This museum contains photographs, oral histories of West Winter Park and the Hannibal Square Timeline, that educates people about the local and national events in African-American history from past to present. Many visitors are touched by the photographs that tell personal stories of the African Americans.

From the museum, you will learn that Hannibal Square is one of the first communities where African Americans could buy and own properties. There is also a visiting exhibition that showcases the cultural and visual artworks by the African Americans such as photography, quilt-making and paintings. After visiting the museum, you can dine in the great restaurants, shop at LaBella for fashions and lingerie, take a shot at the photography studios and tons more.

Hannibal Square Heritage Center

Address: 642 W New England Ave, Winter Park, FL 32789-4134

Website: Hannibal Square Heritage Center

10. Have a romantic or relaxing walk through Central Park

Editor's Note: There's no photo available at the time of writing

Thousands of visitors come to Central Park every year just to appreciate its gracefulness. Walking in the park shaded by oak trees, admiring beautiful fountains and lush landscapes. Central Park offers you a special kind of shopping experience, as it is located in the heart of the downtown shopping district where you can walk and stop. For couples, take a romantic stroll in the rose garden on the south end. If you happen to be here in March, catch the Winter Park Art Festival around the third week of March. And also, bring your food, lie on the grass and have a picnic with your friends or family.

Central Park

Address: 251 S Park Ave, Winter Park, FL 32789

Website: Central Park

11. Feel the historical ambience and architecture of Casa Feliz Historic Home Museum

Originally planned to be torn down, Casa Feliz Historic Home Museum is a restored Spanish farmhouse designed by the acclaimed architect James Gamble Rogers II. The museum is furnished with Spanish roof tiles and century-old bricks. Like a castle, it has a turret, a bell tower and a heavy timber balcony surrounded by a courtyard. Stepping into the museum is like going into the 19th-century of Spain with the ceiling of hand-hewn beams, the European curio, the interior courtyard of Majolica tiles​ and the circular staircase.

The museum is opened every Tuesday and Thursday morning and Sunday afternoon with a recommended donation of 5 USD to support them. On Sunday afternoons, there is ‘Music at the Casa’ where there are different music performances, ranging from jazz, classical, pop, and dance of Latin origin, bluegrass and folk, in the living room.

Casa Feliz Historic Home Museum

Address: 656 N Park Ave, Winter Park, FL 32789-3217

Website: Casa Feliz Historic Home Museum

12. Submerge yourself into jazz music in Blue Bamboo Center for the Arts

Editor's Note: Photo taken from the establishment's official social account

It all started when a jazz musician, Chris Cortez, his wife Melody Cortez, a local artist, and composer and classical musician Mark Piszczek decided to transform a warehouse into a venue for jazz and classical performances, for a recording studio and an art gallery. Their main intention was to stir the local music​ scene so they decided to come back to Orlando. Their performances includes jazz, classical, world music, dance, theatre and spoken word.

Live performances starts at 8.00 pm every evening but the door opens at 7.00 pm. As the seats are limited, be sure to get your tickets in advance, either online or at the door. For retirees, shut-ins or students who cannot bear the expense of the tickets, free Community Tickets are available.

Blue Bamboo Center for the Arts

Address: 1905 Kentucky Ave, Winter Park, FL 32789

Website: Blue Bamboo Center for the Arts

13. Take a look at the exceptional gallery in Cornell Fine Arts Museum

Being the only teaching museum in Orlando, they have over 5,000 exceptional collections that will wow you. It is located on​ the campus of Rollins College. Their collections vary from antiquity to contemporary including paintings from 14th to 21st centuries, prints, drawings and photographs from 15th to 21st centuries, ethnographic objects and watch keys from 16th to late 19th centuries. They have changing exhibitions in the museum throughout the year.

The museum is free of admission every day except Monday. There are free 30-minute tours on weekends to Cornell Fine Arts Museum on Saturdays and to The Alfond Inn in Winter Park, which is a hotel owned by Rollins College, on Sundays. And also, there are Throwback Thursday Tours on the 3rd Thursday of each month and Happy Hour Tours on the 1st Wednesday of each month. Above all that, you will be inspired by the interest and commitment of the staffs there.

Cornell Fine Arts Museum

Address: 1000 Holt Ave, Rollins College, Winter Park, FL 32789-4499

Website: Cornell Fine Arts Museum

Find beauty in this city of blooming arts

There are many hidden treasures in Winter Park, Florida for you to discover. By the end of your trip, you will find yourself with much appreciation of arts and nature beauty. Take a trip and connect​ with your inner world through arts and nature in this fascinating city.