Top 15 Winter Garden Activities You Can’t Miss

Situated along the picturesque southwest shore of Lake Apopka, Winter Garden is a vibrant city, located just 20 minutes from downtown Orlando.

For many years, it was a modest agricultural community primarily focused on the cultivation of oranges and grapefruits. However, since the 1980s, notable transformations have occurred.

Today, Winter Garden boasts a thriving population of approximately 50,000 residents. The city features an award-winning farmers’ market, a contemporary food hall, and a downtown area that can be described as ‘fully developed’.

The 22-mile West Orange Trail winds through the downtown area, contributing to a growing regional network of trails.

Most importantly, the characteristic charm of Central Florida remains prominent, with majestic live oaks lining many streets and a stunning waterfront along Lake Apopka, which serves as a habitat for alligators.

1. Downtown Winter Garden

Located along Plant Street, downtown Winter Garden meets every expectation of a dynamic city. It offers ample shopping, diverse dining options, nightlife, museums, art, and a plethora of community events.

Visitors could easily spend an entire day here without experiencing boredom. A Saturday visit is particularly rewarding, coinciding with one of the best farmers’ markets in the nation.

Alternatively, a Friday visit allows guests to enjoy a complimentary concert at the Centennial Plaza Gazebo.

The entire district has been thoughtfully designed for outdoor engagement, featuring a tree-shaded section of the West Orange Trail that runs through the heart of Plant Street.

Adjacent to the farmers’ market pavilion is the Downtown Interactive Fountain, providing entertainment for children, with water jets surrounded by benches, canopies, and tropical landscaping.

2. Winter Garden Farmers’ Market

Source: Winter Garden Farmers Market / Facebook

During my visit to this inspiring farmers’ market, it had recently been acknowledged as the best in Florida and in the USA by the American Farmland Trust.

Taking place in a grand pavilion every Saturday from 8:00 am to 1:00 pm, the market features over 100 vendors weekly, nearly one-quarter of which are local farms.

This is an excellent opportunity to acquire Central Florida’s renowned fresh produce. Additionally, shoppers can find artisanal baked goods, flowers, houseplants, herbs, arts and crafts, pet supplies, and a delectable selection of local prepared foods.

The market is a significant event, drawing thousands of shoppers each week. A complimentary KidZone offers various activities for children, along with special programming throughout the year.

3. Plant Street Market

Source: Plant St. Market / Facebook

If I were to select one establishment for dining in Winter Garden, it would undoubtedly be this stylish food hall. Operating seven days a week, Plant Street Market accommodates more than 20 vendors.

Among its offerings is a chic chocolate shop and an upscale butcher, with a focus on prepared food and drinks.

Regarding beverages, patrons can enjoy offerings from Crooked Can Brewing Company (mentioned below), Axum Coffee, and AntiquiTeas.

Culinary options span a wide range, including tacos, sushi, raclette, poke bowls, coal-fired pizza, BBQ, ceviche, bento, oysters, donuts, and mac and cheese.

The building features a stripped-back industrial aesthetic, with plentiful seating both indoors and on the patio.

4. Crooked Can Brewing Company

Source: Crooked Can Brewing Company / Facebook

One of the prominent establishments at Plant Street Market is an award-winning craft brewery overseen by a skilled brewmaster.

Crooked Can Brewing offers an extensive selection of core, small-batch, and seasonal brews. Among the three flagship options, my favorite is the refreshing Florida Sunshine Lager, which is ideal for a hot day in Central Florida.

The market’s location allows patrons to easily find the perfect food pairing, with options such as wings, bento boxes, oysters, pizza, empanadas, and mac and cheese in close proximity.

Additionally, the outdoor patio provides a charming atmosphere, with tables nestled under the shelter of majestic live oaks.

5. Newton Park

I was thoroughly captivated by this beautiful park adjacent to Lake Apopka. The lake faced significant environmental challenges in the 20th century, having been declared a dead zone.

Currently, the situation has vastly improved, as evidenced by the vibrant wildlife surrounding Newton Park.

Alligators are frequently spotted, and spending time by the water guarantees sightings of a diverse array of bird species. An informative sign assists with species identification, showcasing everything from roseate spoonbills to various heron types.

Newton Park features a charming footbridge and an extended dock that extends out over the water. Be sure to visit during the evening to witness a breathtaking sunset.

6. Garden Theatre

Since its reopening in 2008, the Garden Theatre has emerged as a cornerstone for the performing arts in downtown Winter Garden. This restored Mediterranean Revival structure dates back to 1935 and initially operated as a single-screen cinema.

The theater closed its doors in 1963 and was later repurposed as a farming supply store for decades. In 2002, the city acquired the building, which underwent restoration through the efforts of the non-profit Winter Garden Heritage Foundation.

Visitors can enjoy Broadway shows, plays, concerts, live comedy, and dance performances here. I attended an impressive production of Dreamgirls and was thoroughly impressed by the venue. The sound and lighting were exceptional, and my view was unobstructed, even from a side seat.

7. West Orange Trail

Increasingly, visitors no longer require a vehicle to navigate much of Central Florida. Winter Garden is one of several communities connected by a 22-mile multi-use trail.

The Orange Trail runs directly through downtown. Additionally, if one does not have access to a bicycle, rentals are available from Wheel Works Bicycle Rentals or West Orange Trail Bikes and Blades.

Traveling north along the trail leads you around the lakeshore toward Apopka, a gateway to the natural springs north of Orlando.

During my visit, the Orange Trail was on the verge of being linked to the expansive 250-mile Coast to Coast (C2C) Connector Trail extending from the Gulf Coast to the Atlantic.

8. Central Florida Railroad Museum

Source: Central Florida Railroad Museum / Facebook

This fascinating museum is located in the historic Tavares and Gulf depot, constructed in 1913. This quaint building hosts a wealth of exhibits beyond initial expectations.

Within its walls, visitors will find numerous railroad artifacts, including uniforms, signs, lamps, clocks, charts, photos, handcars, maps, and much more.

Among the exhibits is a remarkable collection of silver service and dining car china, featuring over 25 patterns from passenger trains across the United States.

Younger visitors are likely to be enchanted by this museum, with the model railroad and interactive Thomas the Tank Engine layout capturing their attention.

9. Winter Garden Heritage Museum

Another museum situated in a former rail depot is the Winter Garden Heritage Museum, housed in the Atlantic Coast Line station (1923) downtown. Visitors here are offered an engaging overview of Winter Garden’s history.

There is a variety of exhibits to explore. I spent approximately an hour examining local Native American artifacts, vintage barber tools, military items, and various artifacts from significant local businesses, ranging from dental offices to car dealerships.

I was particularly intrigued by the accounts of the area’s earliest European settlers and the history of the citrus industry.

Lake Apopka is a recurring theme, with exhibits detailing the lake’s reputation as a recreational fishing destination in the early 20th century.

10. SOBO Museum

Driving the vibrant art scene in Winter Garden is a gallery located in a historic Art Deco building downtown. Originally a Works Progress Administration (WPA) project built during the Great Depression, it served as the city fire station from 1938.

Currently, it houses the Winter Garden Art Association and regularly features new exhibitions.

Shows typically run for two months and showcase the work of artists from across Central Florida.

The gallery is also a hub for art education, offering a comprehensive program of classes and workshops. A significant annual event is Arts in April, alongside a schedule of special exhibits and activities throughout the year.

11. Orange County National Golf Center

A premier destination for avid golfers, the Orange County National Golf Center features two championship 18-hole courses.

Each course possesses unique characteristics. Crooked Cat offers a laid-back, links-style layout with rolling hills along the fairways and expanses of native heather, having hosted an international LIV event during my visit.

In contrast, Panther Lake is slightly more confined, with unexpected elevation changes and holes framed by native pines and various water hazards.

For younger players and those honing their approach skills, the Tooth offers a pristine nine-hole walking course.

The center also boasts a 42-acre driving range, reportedly the largest in the United States, where Tiger Woods showcased his skills in a legendary Nike commercial in 1999.

12. Winter Garden Village

A new chapter for Winter Garden commenced in 2007 with the opening of this open-air mall located south of downtown.

Covering over a million square feet, Winter Garden Village includes a variety of national retailers, including recognizable names such as Target, Marshalls, Bealls, Best Buy, Bed Bath & Beyond, Lowe’s, and PetsMart.

In the walkable northern section, smaller-scale shops and dining establishments are present. Noteworthy shops include a Nike Factory Store and locations for Victoria’s Secret, Forever 21, Kay Jewelers, and Bath & Body Works.

Some dining choices I encountered included Five Guys, Bonefish Grill, Firehouse Subs, Just Salad, and Panera Bread.

13. Tucker Ranch

Located on the southwestern edge of the city, Tucker Ranch, a 200-acre conservation park, had just recently opened at the time of my visit to Winter Garden.

Tucker Ranch sits on the marshy banks of Johns Lake, offering a scenic glimpse of Old Florida, complete with remnants of a historic cattle ranch and numerous venerable live oaks.

The park features a kayak/canoe launch, a playground, and picturesque picnic areas situated beneath the expansive oaks or at the water’s edge.

Along the nature trail, visitors can learn about the property’s long history, dating back to the early 20th century, when it was home to the West Orange Country Club.

14. Withers-Maguire House

Source: Ebyabe / Wikimedia

For an insight into local domestic life from previous eras, the Withers-Maguire House, a beautiful historic house museum, is located just five minutes away in Ocoee.

Constructed in 1888 in the Gothic Stick style, the house was built for a veteran from Kentucky who wintered in the area. Withers was involved in the local citrus industry, as was David O. Maguire, who acquired the property in 1910.

The charming Florida Heart-pine floors and the graceful wraparound porch are notable features, as is the fact that this was one of the first homes in Orange County to incorporate water closets and concealed electric wiring.

The museum is open from Monday to Friday and is available for private events.

15. Escape Goat

Escape rooms have gained tremendous popularity in the entertainment landscape in recent years. For those unfamiliar with the thrill and excitement, Escape Goat in Winter Garden offers an excellent introduction.

The establishment features a variety of themed rooms, providing an engaging, immersive, and creative environment conducive to team-building skills.

During my visit, there were four uniquely themed rooms: Treehouse, a whimsical animal-themed challenge; The Quest, set in a fantastical landscape with magical elements; Area 51, a sci-fi mystery; and A Fisherman’s Tale, a treasure hunt in a historical maritime village. The puzzles are crafted with care, and the theming, effects, and props immerse participants in the experience.