The 12 Best Things To Do In Winter Garden, Florida

An Orlando suburb in the backyard of Disney World, Winter Garden is the real life “Main Street USA.” Here you'll find locals enjoying a stroll down oak-shaded Plant Street, or dining on gourmet farm-to-table meals at locally-run restaurants. Winter Garden’s charming downtown, defined by a wisteria-draped bike trail piercing through its center, is on the National Register of Historic Places. It’s the perfect place to take a slow stroll and pop in the diverse small businesses that thrive in the shadow of the theme park giants.

From art galleries to regional theatre to fresh Florida dining, Winter Garden is a microcosm of rich culture and old Florida charm. It makes a quaint home base for travels and adventures around Orlando.

Whether you're looking for a weekend retreat or a day trip, here’s how to make the most out of your stay in Winter Garden, Florida.

Things To Do

Explore Downtown

Start your day in the heart of Winter Garden on Plant Street, where you'll find a picturesque downtown lined with quaint shops and cafes in historic buildings. Don't miss learning about West Orange County history at the Winter Garden Heritage Museum, the key to understanding the town's rich past rooted in citrus and rail. For the history enthusiasts, you can book historic guided walking tours here.

wghf.org, 21 E Plant St, Winter Garden, FL 34787

Hit the Biking Trail

For a more active day, rent a bike at Wheel Works and embark on a leisurely ride cycling the West Orange Trail. The 22-mile-long trail is repurposed from old rail road tracks and runs through towns, parks, and countryside throughout Central Florida. You’ll share the trail with joggers, skaters, and even pro cyclists training for their next distance race. The West Orange trail connects Florida’s coast-to-coast cycle path.

Meander the Farmers' Market

Shop at the Winter Garden Farmers Market on Saturdays in the downtown pavilion. It's one of the best in Central Florida, offering fresh produce, handmade goods, and a bustling atmosphere with live music. It’s a great spot to pick up Florida honey, fresh bread, local art, a bouquet of flowers, and organic local produce from The Farmacy. Don’t leave without securing a souvenir from the A.B. Newton & Company tent, a local print and design company famous for their regional city map prints.

Indulge in the Arts

When not performing at Disney World, local entertainers stay creative putting up well-produced Broadway shows at the historic Garden Theatre. The vintage-style theatre also hosts classic movie nights and touring productions. For a look at local visual art, stop in SoBo Art Gallery in the town’s turn-of-the-century fire station.

Where To Eat

For such a small town, Winter Garden is a diverse, foodie hub in Central Florida.

Grab a Filling Breakfast

Start with a breakfast of French pastries at Rosalie French Cafe. If their Parisien patio is too crowded with early morning cyclists, Three Birds Cafe and Axum Coffee are just across the cobblestoned street.

Hit up a Local Lunch Spot

For lunch, grab hearty American fare at The Hangry Bison, or join the locals for sandwiches, flatbreads, and burgers at Pammie’s Sammies.

Enjoy a View

Most dining venues in Winter Garden have sidewalk dining to enjoy Florida’s nice winter weather, but it’s on the rooftop of The Whole Enchilada where you’ll catch a breeze and the best view of the busy main street. 

Cozy up at a Local Legend

Lee & Rick’s Oyster Bar has been a Winter Garden legend since 1950. The unadorned local haunt serves up fresh oysters and has a loyal following of local regulars.

leeandricksoysterbar.com, 5621 Old Winter Garden Rd, Orlando, FL 32811

Hit the Town for Dinner

For dinner, indulge in a The Chef’s Table at the Edgewater, Winter Garden’s historic hotel. This intimate restaurant offers a three-course prix-fixe menu that changes regularly, featuring the fresh Florida seasonal ingredients. In the same locally-inspired fashion, Market to Table also serves a modern American menu using southern ingredients, like Florida farm-raised chicken.

Grab a Round

For an after dinner aperitif, head to Pilar’s Martini in the Roper Garden Buildling for a cocktail and live music. The Roper Garden Building was built in 2008 as the first Certified Green Building in Winter Garden and features an aquaponic green house on the roof.

No visit to Winter Garden is complete without a stop at Crooked Can Brewing Company within the Plant Street Market. This craft brewery offers a variety of beers brewed on-site, from hoppy IPAs to smooth stouts—you can even take a tour of their facility. Pair your drink with a snack from one of the market’s food vendors specializing in snacks like gourmet mac n cheese, wood-fired pizza, or instagram-worthy acai bowls from Press’d Juice Bar.

Where To Stay

Choose a Historic Stay

Take in the charm of this town with a stay at the historic 1926 Edgewater Hotel. The bed-and-breakfast maintains its historic ambience with tasteful period decor. Located right on Plant Street, it's the perfect base for exploring Winter Garden without needing to get in a car.

historicedgewater.com, 99 W Plant St, Winter Garden, FL 34787

Stay at a Charming Retreat

In the neighboring town of Oakland, you can get the same Old Florida experience staying in an authentic 1900s home at Oakland Manor House. The screened, wraparound porch is shaded in Spanish Moss and steps from Lake Apopka. 

oaklandmanorhouse.com, 620 N Tubb St, Oakland, FL 34760