Winter Park is one of Orlando’s most upscale suburbs. The city boasts boutique shops, fancy restaurants, and wealthy residents. But even if you’re on a tight budget, you can still find fun things to do in Winter Park.
The city of Winter Park offers a blend of culture and nature in one place. It has scenic lakes, well-kept parks, and small but interesting museums and galleries. Winter Park’s attractions are concentrated in the historic downtown area, while others are just a short drive away.
Explore the city without breaking the bank with this list of 12 totally free things to do in Winter Park.
1. Window Shopping on Park Avenue
The first time my parents visited Park Avenue with me, my mother commented that it looked like Europe. The brick-paved streets and quaint shops give this main street an Old-World feel.
Make sure to wander down the side streets and poke around the buildings. Park Avenue is full of little surprises. Look up at the Pottery Barn, and you’ll see the vintage sign from when it used to be the Colony movie theater. There’s a building with a koi pond in the lobby, and a secret alleyway with shops tucked away.
And there are plenty of shops to browse. You’ll find national chains such as Williams-Sonoma and local favorites such as the Writers Block Bookstore. You can park for free on the street, or on the 4th or 5th levels of the Park Place Parking Garage at 150 W. Canton Avenue.
2. Central Park
If you need a break from window shopping, head over to Central Park. This big, grassy area in the middle of Park Avenue is a great place to unwind in between browsing the shops.
In Central Park, you’ll find a small but beautiful rose garden, the SunRail train depot, and benches for seating. Bring a picnic and a good book, or just do some people-watching. It’s one of the most relaxing things to do in Winter Park.
Central Park is where all the action happens on Park Avenue. In March, it hosts the annual Winter Park Sidewalk Art Festival. In July, it’s home to a charmingly old-fashioned Independence Day celebration.
You can also catch free movies on the lawn. The Enzian Theater hosts its Popcorn Flicks in the Park series here (which I mentioned in my post about Maitland).
3. Winter Park Farmers Market
On Saturday mornings from 8am-1pm, the Winter Park Farmers Market transforms Central Park into a bustling hub of activity. It’s one of the most popular things to do in Winter Park. Visitors come here to buy fresh produce, plants, baked goods, coffee, and more.
While there is a free parking lot near the market, it tends to fill up as the morning progresses. It’s best to arrive early in the day if you want to easily find a spot.
Address: 200 W. New England Avenue, Winter Park, FL 32789
4. Winter Park History Museum
After exploring the Winter Park Farmers Market, take a short walk to the Winter Park History Museum.
This free museum traces Winter Park’s beginnings as a tourism destination for wealthy Northerners. Despite its small size, the museum is interesting and provides a nice break from the Florida heat.
If you want to dive deeper into Winter Park’s history, you can download a free self-guided walking tour of downtown Winter Park. It’s a neat little tour that offers bite-sized nuggets of history.
Address: 200 W. New England Avenue, Winter Park, FL 32789
5. Hannibal Square Heritage Center
Established in 1881, Hannibal Square was a thriving neighborhood filled with free Black families. However, in recent years, developers have moved in and gentrified the area. The Hannibal Square Heritage Center seeks to preserve the community’s history.
This free museum showcases old photos capturing the lives of Hannibal Square residents in the past century. You can also check out a timeline of local and national events in African-American history, as well as rotating exhibits and educational programs.
Like the Winter Park History Museum, the Hannibal Square Heritage Center fits a lot of information into a small space. It’s a great resource for the community and highlights an important part of Winter Park’s history.
Address: 642 W. New England Avenue, Winter Park, FL, 32789
6. Kraft Azalea Garden
If you visit Kraft Azalea Garden, chances are you’ll see someone posing for a photo. This park near Lake Maitland is a popular spot for engagement shoots and other photoshoots.
But it’s no wonder. With cypress trees draping over the landscape, a white-columned monument overlooking the water, twisted banyan trees straight out of a fantasy novel, and serene lake views, Kraft Azalea Garden is one of the most romantic places in Central Florida. You can even get married here.
Just spend some time wandering around the park. There are many photo opportunities, and it’s one of the most beautiful things to do in Winter Park.
Kraft Azalea Garden is in a residential area, so parking is limited. Your best bet is to visit in the mornings.
Address: 1365 Alabama Drive, Winter Park, FL 32789
7. Mead Botanical Garden
Mead Botanical Garden makes you feel like you’re in the woods, even though downtown Orlando is just a quick drive away. It’s one of my favorite things to do in Winter Park.
The park includes a butterfly garden, boardwalk, and bike trail within nearly 48 acres of greenery. It’s a great place for birdwatching and hiking. Or you can bring your lunch and relax at one of the picnic tables or pavilions.
Like Kraft Azalea Garden, it’s a great place to take photos. The park is open from dawn until dusk.
Address: 1300 S. Denning Drive, Winter Park, FL 32789
8. Rollins Museum of Art
The Rollins Museum of Art at Rollins College has an extensive collection of paintings, photographs, sculptures, and more that you can view for free. The museum is open Tuesdays through Sundays.
The museum switches out their exhibits, so make sure to visit their website to see what’s on display. And if you want to see even more art from their collection, head over to the nearby Alfond Inn.
After you’re done at the museum, take some time to walk around historic Rollins College. It’s considered one of the most beautiful campuses in America.
Address: 1000 Holt Avenue, Winter Park, FL 32789
9. Casa Feliz
Winter Park almost lost one of its architectural treasures, Casa Feliz.
This house was built in 1933 at 656 N. Interlachen Avenue in Winter Park. It was facing demolition in 2000. But the city government rescued the house and moved it to its current location next to the Winter Park Country Club golf course.
Casa Feliz resembles a Spanish farmhouse. The interior has been restored and features a circular staircase and interior courtyard. You can take a free tour of Casa Feliz from 10am-12pm on Tuesdays and Thursdays.
Address: For directions to the parking lot, set your GPS coordinates to 28.6030° N, 81.3502° W. (Google Maps doesn’t provide a route with vehicle access if you enter the home’s actual address.)
10. Cady Way Trail
If you’re looking for sporty things to do in Winter Park, grab your bike and ride down the Cady Way Trail. This bike path runs from Aloma Avenue at Hall Road in Winter Park to Lake Druid Park in Orlando.
The Cady Way Trail includes the bike bridge over 436 near Aloma. The trail passes through the Audubon Park, Baldwin Park, Colonial Town Center, and Coytown neighborhoods of Orlando. Just watch out for cars, as there are suburban road crossings throughout the trail.
In Winter Park, you can access the Cady Way Trail from Goldenrod Park or Cady Way Park.
11. Crealdé Contemporary Sculpture Garden
Crealdé is a local school that began as an art colony. The school offers all kinds of art classes and workshops.
At the Crealdé campus, you’ll find a Contemporary Sculpture Garden featuring 60 outdoor art pieces and educational panels. You can take a self-guided tour of the garden and learn about different sculpture styles and materials.
The sculpture garden is open every day from 9am-4pm.
Address: 600 St. Andrews Boulevard, Winter Park, FL 32792
12. Howell Branch Preserve
Located off Howell Branch Road, Howell Branch Preserve is a 50-acre wetland that’s home to numerous animal species.
Howell Branch Preserve is small, but there’s a boardwalk with an observation deck and picnic tables overlooking the wetlands. There’s also a park area with a playground, pavilion, and fitness equipment. It’s a low-key place to spend some time in nature.
Address: 1205 Howell Branch Road, Winter Park, FL 32789
Bonus: Charles Hosmer Morse Museum
I didn’t include this museum in the original list because it’s only free at certain times of the year. However, it’s worth mentioning because it’s hands-down one of the best things to do in Winter Park.
The Charles Hosmer Morse Museum is free on Friday nights from November-April and on July 4. The museum features the world’s largest collection of art from Louis Comfort Tiffany, the creator of Tiffany glass. The collection is stunning, especially the Tiffany Chapel created for the 1893 World’s Fair.
If you haven’t checked out the Morse Museum yet, you should definitely put it on your to-do list. It’s a great museum, and even better when it’s free.
Conclusion: 12 Totally Free Things to Do in Winter Park, FL
Despite the city’s upscale reputation, these 12 things to do in Winter Park won’t stress your wallet.
Winter Park combines a beautiful natural landscape with a charming vintage feel. And because most of the free activities are in or around the historic downtown area, you won’t have to go far to experience them. Whether you’re local or a visitor, it’s worth spending a day checking out Winter Park.