If you recently moved or are planning to move to Winter Garden, Florida, we want to applaud your decision-making skills. As any of its 40,000 residents will tell you, the city is a great place to live—with lots to do, rain or shine.

Established in 1908 along Lake Apopka, Winter Garden exudes old Florida charm with a history rooted in the state’s citrus and railroad industry. 

But that doesn’t mean this small city lacks amenities. 

Winter Garden is known for its quaint but active downtown, farmer’s markets, many parks, local events, and mere 30-minute drive to downtown Orlando and Central Florida’s best theme parks. Due to the West Orange Trail, it’s recognized as one of Florida’s “Trail Towns”—a vibrant destination where trail users can venture off trail to enjoy the amenities and heritage of the local community.

This and more makes for numerous fun things to do in Winter Garden. So, whether you’re planning your weekend or looking for a new favorite hangout, you won’t be disappointed.

You’ll find over 56 possibilities in this comprehensive guide, so let’s dive in.

Exploring Downtown Winter Garden

Winter Garden’s downtown district is the perfect place for a stroll or a day on the town. At its core is Plant Street, lined with various eclectic storefronts and dining options. You’re also likely to spot historic architecture or catch some live music, but be sure to spend some time in the following locations. 

Note: You’ll find that many of the activities in this guide are in downtown Winter Garden. We’ve organized them by category, but if they are downtown, it will say so in the description. 

1. Centennial Plaza 

The Centennial Plaza is the perfect place to rest mid-stroll, read a book, or people-watch. Claim a spot on one of the benches or swings circling the plaza fountain, and snap a picture with the iconic clock tower before you leave. 

Location: 101 West Plant Street (Downtown)

2. Splash Pad & Pavilion

This large splash pad in downtown is both picturesque and the perfect play place for children. It also features a large pavilion great for picnics and parties. 

Location: 119 S Lakeview Ave (Downtown)
Hours: 9am to 9pm

3. The National Register Historic District

Within downtown is a 116-acre district that’s on the National Registry of Historic Places. A day exploring these many blocks will take you past several well-preserved historic buildings, including the old fire station, train depot, Edgewater Hotel, and more.

Location: view the map (Downtown)

Enjoy the Art and Music of Winter Garden

4. The Garden Theater

Built in 1935, the Garden Theater resides in the historic part of downtown. Between film showings, live theater, and concerts, the schedule always has something for everyone. 

Location: 160 W Plant St (Downtown)

5. SOBO Gallery

Run by the Winter Garden Art Association, the SOBO gallery hosts art exhibits, workshops, and special events. A bonus? The historic building located downtown is a renovated firehouse. 

Location: 127 S Boyd St (Downtown)

6. Fridays on the Plaza 

A local favorite, the city of Winter Garden hosts “Fridays on the Plaza,” where you can catch free live music every Friday night at the Centennial Plaza gazebo.

Location: 101 West Plant Street (Downtown)
Hours and Lineup: view the schedule

7. Art in Public Places

Another free opportunity to immerse yourself in local culture, the “Art in Public Places” program puts on frequent art exhibits in the City Hall Lobby. 

Location: 300 W Plant St (Downtown)
Hours and Exhibits: view the schedule 

Must-See Markets and Shopping in Winter Garden

8. The Winter Garden Farmers Market

The Winter Garden Farmers Market is an award-winning market put on every Saturday morning at the downtown pavilion. Featuring over 100 vendors, including over 20 local farms, this weekend market is the perfect place to snag local produce, homemade baked goods, soaps, and more. Have a leash? Even your furry friend is welcome.

Location: 104 S Lakeview Ave (Downtown)
Hours: 8am to 1pm 

9. Plant Street Market

The Plant Street Market is an indoor craft market featuring over 20 vendors offering handmade goods and organic foods seven days a week. 

Location: 426 W Plant St (Downtown)
Hours and Vendors: view the schedule 

10. Winter Garden Village

The Winter Garden Village is a large and pleasant outdoor mall at Fowlers Grove. If you’re in need of some retail therapy, here you’ll find top national retailers alongside several local shops and options for grabbing a bite.

Location: 3251 Daniels Rd

11. Driftwood Market 

The Driftwood Market is a local boutique with everything from decor, art, and plants to beauty products, jewelry, and more.

Location: 46 W Plant St (Downtown)

12. Adjectives Market

Looking for furniture or decor to add just the right touch to your home? Whether you prefer a modern or vintage look, the Adjectives Market is the local spot for you. 

Location: 137 W Plant St (Downtown)

13. The Boutique on Plant

The Boutique on Plant is a popular shop that carries unique women’s clothing and accessories for all tastes. 

Location: 111 W Plant St (Downtown)

Soak Up History at Winter Garden’s Museums

14. Winter Garden Heritage Museum

The Heritage Museum showcases over 5,000 pioneer and Native American artifacts from Orange County’s history.

Location: 1 N Main St (Downtown)
Admission: Free; donations suggested

15. Central Florida Railroad Museum

This local museum is dedicated to Central Florida’s historic contribution to the railroad industry. Among its exhibits are a caboose and a 1938 Fairmont motorcar.

Location: 101 S Boyd St (Downtown)
Admission: Free; donations suggested

16. Withers-Maguire House

The Withers-Maguire House is technically located in Ocoee, FL, but is a short 10-minute drive from Winter Garden. Built in 1888, this over 130-year-old house (and everything in it) has been restored to original condition. The home is rented out for events, but you can schedule a tour in advance. 

Location: 16 E Oakland Ave, Ocoee
Admission: Free

Fun Outdoors: Winter Garden Parks and Trails

17. West Orange Trail

The West Orange Trail is a renowned 22-mile paved trail between Winter Garden and Apopka that’s perfect for biking, hiking, rollerskating—you name it. The trail passes through downtown Winter Garden, with playgrounds along it.

Location: 501 Crown Point Cross Rd

18. Lake Apopka

Spanning 30,000 acres, Lake Apopka is the fourth-largest lake in Florida. With the city nestled up to the lake, it has become a popular spot for boating, canoeing, kayaking, and fishing. 

19. Tucker Recreational Park and Nature Preserve

Next to Johns Lake, this 200-acre conservation park has something for everyone. Choose from walking the nature trail, enjoying the picnic areas, or using the canoe and kayak launch. Did we mention it’s pet-friendly (on leash) and known to have well-kept bathrooms?

Location: 70 Tucker Rd
Hours: 8am to 5pm (extended to 6pm from March through October)

20. Chapin Station

This simple community park borders the West Orange Trail and has basketball and tennis courts available.

Location: 501 Crown Point Cross Rd
Hours: sunrise to sunset

21. Winter Garden Station

Another simple playground along the West Orange Trail, Winter Garden Station is a great place to rest on your hike or take the kids for some Vitamin D. 

Location: 455 E Plant St
Hours: sunrise to sunset

22. Newton Park

Named after the city’s first Mayor, A. B. Newton, this lake-front park is known for its stunning sunset views. Its amenities include a playground, picnic tables, grills, restrooms, boat ramp, and boardwalk.

Location: 31 W Garden Ave
Hours: 7am to 10pm

23. Braddock Park

This neighborhood park features a playground, baseball and softball diamond, and a soccer field. 

Location: 13460 Lake Butler Boulevard

24. Maple Street Park

One of the larger neighborhood parks, Maple Street Park has something for everyone between a playground, basketball court, racquetball court, volleyball court, and skate ramp. Leashed pets are allowed, and there are picnic areas and grills. 

Location: 142 E Maple St

25. Dr. Bradford Memorial Park

Dr. Bradford Memorial Park is a small, well-maintained park most notable for its fishing canal that connects to Lake Apopka. The park is often used for picnicking and fishing on the canal. 

Location: 220 W Division St

26. Warrior Park

While Warrior Park is primarily a large open field with some trees for shade, it’s a great choice for when you want to take your pup without running into too many people. 

Location: SE Corner of Windermere and Warrior Roads

27. Veterans Memorial Park

Another large community park you’ll love if you enjoy outdoor sports is the Veterans Memorial Park, which offers a baseball and softball diamond, basketball court, tennis court, and volleyball court. The park also has a grill, picnic areas, and a playground. 

Location: 420 S Park Ave

28. West Orange Dog Park

The West Orange Dog Park has two divisions—one for bigger and smaller dogs. Both areas include bowls of water, doggy obstacles, and benches for owners to watch their friends play. 

Location: 12400 Marshall Farms Rd

29. Oakland Nature Preserve 

This 150-acre nature preserve is technically located in Oakland, FL, but is a mere 10-minute drive from downtown Winter Garden. While donations are accepted, access to the hiking trails and museum is free. 

Location: 747 Machete Trail, Oakland

Getting Your Golf On in Winter Garden

30. Orange County National Golf Center

Based in Winter Garden, FL, the Orange County National Golf Center and Lodge boast a premier golf academy, the largest driving range and practice facility in America, and the famous Crooked Cat and Panther Lake golf courses.  

Location: 16301 Phil Ritson Way

31. West Orange Country Club

Since 1967, the West Orange Country Club has offered club members a serene experience on their 18-hole golf course. 

Location: 3300 W Orange Country Club Dr

Food and Drink for Your Winter Garden Taste Buds

32. Crooked Can Brewing Company

This acclaimed craft brewery is located downtown and forms the base of the plant street market. You’re welcome to grab food from nearby vendors and eat it here with something to wash it down. 

Location: 426 W Plant St (Downtown)

33. The Attic Door

When it comes to the nightlife in downtown Winter Garden, The Attic Door is hard to beat. This cozy, low-lit wine bar offers eclectic decor, small plates, and live music. 

Location: 28 W Plant St (Downtown)

34. Pilars

Another hot spot, Pilars is a piano bar that serves 1930s art-deco decor with mixed drinks and martinis. 

Location: 146 W Plant St STE 120 (Downtown)

35. Rosallie le French Cafe

Looking for a cute place to consume your daily caffeine or meet up with a friend? This French cafe has you covered with delicious coffee, pastries, and all-day brunch.

Location: 141 W Plant St (Downtown)

36. Axum Coffee 

In need of coffee again—or maybe a baked treat? This local coffee shop is just as colorful and tasty.   

Location: 146 W Plant St STE 110 (Downtown)

37. Try One of Many Popular Restaurants

With the dining experiences available in Winter Garden, you’ll always eat well. But what are you in the mood for right now? Well, that changes. 

Whether it’s take-out, weekend date night, or a special occasion, the following restaurants are a great place to start exploring the local food scene. 

Even More Activities in Winter Garden, FL

That’s right; there are still more things to do in Winter Garden, and the guide continues. Try one of these ideas the next time you want to cool off, learn something new, or have a little thrill. 

38. Farnsworth Pool

If you don’t have a pool at home, the Farnsworth public pool is one way to keep cool and have fun this summer. It also hosts public swimming sessions and offers family specials.

Location: 1 Surprise Dr
Admission and Hours: view current information

39. West Orange Trail Bikes & Blades

Don’t have a bike? Rent one from this local business to explore the town or West Orange Trail in a new way and test if getting one is worth it. They also offer guided tours. 

Location:  17914 FL-438, Winter Garden

40. Green Mountain Scenic Byway

The Green Mountain Scenic Byway is a 45-mile winding road through the rolling hills between Winter Garden and Mount Dora. The route draws cyclists and motorcyclists, so drive carefully. 

Location: view the map

41. The Winter Garden Library 

It may have the charm of a small-town library, but the Winter Garden Library still provides all the resources available through the Orange County Library System. Go to pick out a book and read, for one of their events, or a cute date. 

Location: 805 E Plant St (Downtown)
Events: view the schedule

42. Escape with Horses

If you love horses, give horseback riding lessons a shot. Escape With Horses also offers reservations for group events and parties.

Location: 4316 Avalon Rd

43. Jodi’s Ski School

Water skiing can be just as fun as skiing down the side of a mountain, and there’s plenty of opportunity for it in Florida. Jodi’s Ski School in Winter Garden offers professional water ski training.  

Location: 13801 Avalon Rd

44. The Dive Place

Whether you want to take scuba diving lessons or join in group adventures, The Dive Place offers several exciting opportunities to get out there. 

Location: 15502 Stoneybrook W Pkwy #128

45. American Ghost Adventures

American Ghost Adventures offers a two-hour Winter Garden tour if you’re looking for spooky fun. Highlights include behind-the-scenes access to some of Winter Garden’s historic buildings.

Location: Tours start at 1 N Main St. 

46. Escape Goat

Escape Goat is a local Winter Garden escape room that offers several themed experiences. If you’re looking for family-friendly activities, they allow children five years and up. 

Location: 1165 E Plant St #2 

Day Trips: Theme Parks and Attractions Near Winter Garden

Winter Garden is only 13 miles from Orlando, FL, and close to Central Florida’s most loved attractions, including the following. 

47. Walt Disney World Resort

This world-famous theme park includes Magic Kingdom, Epcot, Disney’s Hollywood Studios, and Disney’s Animal Kingdom—but you probably already knew that. 

Drive from Winter Garden: 30 minutes

48. Universal Orlando Resort

Universal Orlando Resort includes Universal Studios Florida (featuring the Wizarding World of Harry Potter) and Islands of Adventure. 

Drive from Winter Garden: 40 minutes

49. SeaWorld Orlando

This extensive marine theme park features animal exhibits, live shows, and rides.

Drive from Winter Garden: 45 minutes

50. LEGOLAND Florida Resort

If your kid loves Legos, they’ll love this park with LEGO-themed rides, shows, and other attractions.

Drive from Winter Garden: 1 hour 20 minutes

51. Fun Spot America

Fun Spot America features amusement park rides, go-karts, arcade games, and more for family-friendly fun.

Drive from Winter Garden: 40 minutes

52. Gatorland

This 110-acre wildlife preserve is a Florida must. It’s full of alligators and crocodiles and has an aviary, petting zoo, shows, and zip lines. 

Drive from Winter Garden: 30 minutes (or 45 minutes without tolls)

The Best Annual Winter Garden Events to Attend

The city of Winter Garden puts on several events throughout the year. You can find upcoming events on the city website, but these are the annual events you won’t want to miss.

53. Winter Garden Heritage & Music Festival

This annual festival in historic downtown is a free all-day celebration with live music and entertainment across several stages, guided history walking tours, a kids’ zone area, historical exhibits, and more.

54. Spring Fever in the Garden Festival

Celebrate spring each year with this downtown festival that includes various vendors and live entertainment, a chalk art contest, a kids’ zone, nature-related arts and crafts, and more.

55. Party in the Park

Every 4th of July, Winter Garden puts on one of the best firework displays in the county, accompanied by music, food, vendors, and games. (If you own a home, don’t forget to prepare your house for the holiday before you head out.) 

56. Winter Garden Christmas Parade

A Winter Garden tradition, the holiday parade features several floats, local organizations, and more.

Experience All Winter Garden Has to Offer

For a quaint town, Winter Garden has a surprising amount of things to do—no matter your interests. And if you know where to look, you’ll find more hidden gems than you know what to do with. 
If you’re already in the city, we encourage you to try something new this weekend. And if you’re still looking for your new home in Winter Garden, you have much to look forward to.