15 Best Things to Do in Winter Garden (FL)

Written by Bart Meeuwesen
Updated on
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On the beautiful southwest shore of Lake Apopka, Winter Garden is a spirited city, just 20 minutes from downtown Orlando.

For decades this was a small agricultural community, mostly growing oranges and grapefruits. Since the 1980s things have changed in a big way. 

Now Winter Garden is a flourishing city of 50,000. There’s an award-winning farmers’ market, a modern food hall, and a downtown that I can only describe as ‘complete’.

The 22-mile West Orange Trail passes through downtown and is linking up with a regional network of trails as I write. 

Best of all, you’ll never lose sight of the fact you’re in Central Florida. Majestic live oaks line most of the streets, and there’s a stunning waterfront by Lake Apopka, a haven for gators.

1. Downtown Winter Garden

Set along Plant Street, Winter Garden has a downtown that hits every mark. That means a city’s worth of shopping, dining, nighttime entertainment, museums, art, and lots of community events.

I could spend a whole day here and not get bored. The best day would surely be a Saturday, in time for one of the best farmers’ markets in the country. 

Or maybe that should be a Friday, when you can watch a free concert at the Centennial Plaza Gazebo.  

The whole district has been designed for people to spend time outside. A tree-shaded stretch of the West Orange Trail runs right through the middle of Plant Street.

Meanwhile, next to the farmers’ market pavilion is the Downtown Interactive Fountain. All kinds of fun for little ones, these water jets are bordered by benches, canopies and tropical landscaping.

2. Winter Garden Farmers’ Market

Winter Garden Farmers MarketSource: Winter Garden Farmers Market / Facebook
Winter Garden Farmers’ Market

When I shopped at this inspiring farmers’ market it had recently been voted the best in Florida and the USA by the American Farmland Trust.

At a stately pavilion, the market takes place every Saturday from 8:00 am to 1:00 pm. There are more than 100 vendors each week, almost a quarter of which are local farms.

This is an excellent way to get hold of Central Florida’s famous fresh produce. You can also shop for artisanal baked goods, flowers, houseplants, herbs, arts and crafts, pet supplies, and an appetizing choice of local prepared foods.

The market is a real event, attracting thousands of shoppers every week. There’s a free KidZone providing all sorts of activities for wee ones, and special programming throughout the year.

3. Plant Street Market

Plant Street MarketSource: Plant St. Market / Facebook
Plant Street Market

If I had to pick one place to grab a bite in Winter Garden it would be this stylish food hall. Open seven days a week, Plant Street Market houses more than 20 vendors.

There’s a chic chocolate shop, and an upscale butcher—apart from that, this place is about prepared food and drink.

On the beverage side, there’s Crooked Can Brewing Company (more below), Axum Coffee and AntiquiTeas.

Food-wise the choice runs the gamut from tacos to sushi, raclette, poke bowls, coal-fired pizza, BBQ, ceviche, bento, oysters, donuts, and mac and cheese. 

The whole building has a stripped-back industrial feel, and there’s a lot of seating inside or out on the patio.

4. Crooked Can Brewing Company

Crooked Can Brewing CompanySource: Crooked Can Brewing Company / Facebook
Crooked Can Brewing Company

One of the big tenants at Plant Street Market is an award-winning craft brewery run by an expert brewmaster.

On tap at Crooked Can Brewing is a wide choice of core, small-batch, and seasonal brews. My pick of the three flagships is the refreshing Florida Sunshine Lager, perfect for a sweltering day in Central Florida. 

The great thing about the market location is that you don’t need to search hard for the perfect food pairing. You’ve got wings, bento boxes, oysters, pizza, empanadas, mac and cheese and much more moments away.

Meanwhile, outside there’s a lovely patio, with tables under the canopy of majestic live oaks.

5. Newton Park

I have to say, I was completely smitten by this gorgeous park next to Lake Apopka. That body of water had a difficult few decades in the 20th century when it was declared a dead zone.

Things are going much better today, as you’ll see from the abundant wildlife around Newton Park.

Gators are never far away, but if you spend a few minutes by the water you’re sure to see a lot of birds here. There’s a sign that will help you identify the species, ranging from roseate spoonbills to a variety of herons. 

Newton Park has an adorable little footbridge, and a long dock leading over the water. Make sure to be here late in the day for a golden sunset.

6. Garden Theatre

Since 2008 the Garden Theatre has been a beacon for the performing arts in downtown Winter Garden. This restored Mediterranean Revival building goes back much further to 1935, and opened as a single-screen cinema.

The theater closed in 1963 and served as a farming supply store for decades. The city purchased the building in 2002, and the non-profit Winter Garden Heritage Foundation carried out a restoration.

Come for Broadway shows, plays, concerts, live comedy, and dance performances. I caught a dazzling production of Dreamgirls, and can’t praise the venue enough. The sound and lighting were perfect, and I had a clear view, despite sitting off-center.

7. West Orange Trail

Increasingly, you don’t need a car to travel across a lot of Central Florida. Winter Garden is one of a string of communities on the route of a 22-mile multi-use trail

The Orange Trail runs right through downtown. On top of that, if you don’t have your own bicycle you can rent one from Wheel Works Bicycle Rentals or West Orange Trail Bikes and Blades.

Head north and the trail will take you around the lakeshore to Apopka, which is a gateway to the natural springs north of Orlando.

When I was in town, the Orange Trail was about to become a link in the 250-mile Coast to Coast (C2C) Connector Trail, from the Gulf Coast to the Atlantic.

8. Central Florida Railroad Museum

Central Florida Railroad MuseumSource: Central Florida Railroad Museum / Facebook
Central Florida Railroad Museum

This engaging museum is housed in the historic Tavares and Gulf depot, built in 1913. This dainty little building holds a lot more exhibits than I thought it would.

Every available surface inside is covered with local railroad artifacts. I saw uniforms, signs, lamps, clocks, charts, photos, handcars, maps, and heaps more.

In showcases there’s also an exceptional display of silver service and dining car china, with over 25 patterns from passenger trains across the United States.

Naturally younger kids will be spellbound by this museum. They’re sure to love the model railroad, and the interactive Thomas the Tank Engine layout.

9. Winter Garden Heritage Museum

Another museum in a former rail depot, this attraction is in the Atlantic Coast Line station (1923) downtown. At this cute building you’ll be given a whirlwind tour of Winter Garden’s history.

There’s much to see. I spent about an hour perusing local Native American artifacts, old-time barber tools, military items, and all kinds of pieces from prominent local businesses. These range from dentist offices to car dealerships.

I was especially interested in the biographies of the area’s earliest European settlers, as well as the details about the citrus industry.

Lake Apopka is also a recurring theme. You can learn about the lake’s days as a recreational fishing hotspot in the first decades of the 20th century.

10. SOBO Museum

Driving Winter Garden’s exciting art scene is a gallery in an Art Deco building downtown. A Works Progress Administration (WPA) project, this was raised during the Great Depression and served as the city’s fire station from 1938. 

Today it’s the home of the Winter Garden Art Association, and there will be something new every time you visit. 

Shows here generally last for two months and feature the work of artists from across Central Florida.

The gallery is also a center for art education, with a full program of classes and workshops. The big annual event meanwhile is Arts in April. Throughout there’s a schedule of special exhibits and activities.

11. Orange County National Golf Center

A place for discerning golfers, the Orange County National Golf Center has two 18-hole championship courses.

These have different characters. Crooked Cat has a loose, links-style layout, with rippling mounds tracing the fairways, and large patches of native heather. This course hosted an international LIV event when I wrote this article.

Panther Lake meanwhile is a little tighter, with surprising elevation changes and holes framed by native pines and ample water hazards.

For younger players, and people developing their approach play there’s the Tooth, a pristine nine-hole walking course. 

Also at this facility is a 42-acre driving range described as the largest in the United States. In 1999 Tiger Woods showed off his trick shot skills at this very place in a now legendary Nike commercial.

12. Winter Garden Village

A new chapter for Winter Garden began in 2007 when this open-air mall opened south of downtown. 

Spread across more than a million square feet, Winter Garden Village has a roster of national retailers. Think giants like Target, Marshalls, Bealls, Best Buy, Bed Bath & Beyond, Lowe’s and PetsMart.

In the walkable north end there’s a sprinkling of smaller-scale shops and restaurants. Here you’ve got a Nike Factory Store and locations for Victoria’s Secret, Forever 21, Kay Jewelers, and Bath & Body Works.

A few dining picks when I was here were Five Guys, Bonefish Grill, Firehouse Subs, Just Salad, and Panera Bread.

13. Tucker Ranch

On the southwest side of the city, this 200-acre conservation park has only just opened when I visited Winter Garden.

Tucker Ranch is on the marshy shores of Johns Lake, and offers an idyllic glimpse of Old Florida. You’ll see the vestiges of historic cattle ranch, as well as lots of venerable live oaks.

There’s a kayak/canoe launch on the water, a playground, and scenic picnic areas. These are under those giant oaks, or near the water’s edge.

On the nature trail you can learn about the long history of this property, going back to the early 20th century when the West Orange Country Club was here.

14. Withers-Maguire House

Withers-Maguire HouseSource: Ebyabe / Wikimedia
Withers-Maguire House

For a taste of local domestic life in bygone days there’s a beautiful historic house museum 5 minutes away in Ocoee.

In the Gothic Stick style, the Withers-Maguire House was built in 1888 for a Kentuckian veteran who wintered here. Withers was engaged in the local citrus industry, as was David O. Maguire, who purchased the house in 1910. 

I love the Florida Heart-pine floors and the elegant wraparound porch. I was also intrigued to learn that this was one of the first residences in Orange County to have water closets and concealed electric wiring. 

The home is open Monday through Friday, and can be rented for private events.

15. Escape Goat

<yoastmark class=Source: Escape Goat / Facebook

Escape rooms have burst onto the entertainment scene in recent years. If you’ve never experienced the thrill and suspense, Escape Goat in Winter Garden is a fine intro. 

Featuring a variety of themed rooms, Escape Goat offers a fun, immersive and creative environment for groups to build teamwork skills. 

There were four rooms when I came here, each with a very different flavor. Treehouse was a whimsical animal-themed challenge. The Quest has a fantasy setting, with magic and dragons.

Area 51 is a sci-fi mystery, while A Fisherman’s Tale is a treasure hunt in an old-time maritime village. The puzzles are put together with a lot of love, while the theming, effects, and props made it easy for me to be swept along with the story.

15 Best Things to Do in Winter Garden (FL):

  • Downtown Winter Garden
  • Winter Garden Farmers' Market
  • Plant Street Market
  • Crooked Can Brewing Company
  • Newton Park
  • Garden Theatre
  • West Orange Trail
  • Central Florida Railroad Museum
  • Winter Garden Heritage Museum
  • SOBO Museum
  • Orange County National Golf Center
  • Winter Garden Village
  • Tucker Ranch
  • Withers-Maguire House
  • Escape Goat