The City of Winter Garden

Nestled on the banks of Lake Apopka, Winter Garden is a robust city built around small businesses and a thriving downtown area. It’s centered around Plant Street and listed on the National Registry of Historic Places. It also offers museums and access to the 21-mile West Orange Trail.

Winter Garden’s downtown district is centered on the main thoroughfare, Plant Street, which features historic architecture and some of the Orlando area’s best dining and entertainment. The centerpiece is Plant Street Market, a community hub with 20 vendors offering organic eats and handmade products.

Top Winter Garden dining options also include Market to Table, Bosphorous Turkish Cuisine, 4 Rivers Smokehouse, Gyu-Kaku Japanese BBQ, and Urban on Plant Kitchen & Bar, as well as one of Central Florida’s finest dining experiences at Chef’s Table at the Edgewater. You can also get southern-style comfort food at Country House Restaurant or dine on authentic Italian at Bella Italia Ristorante.

Minutes from Winter Garden proper, the town of Ocoee has RusTeak Restaurant & Wine Bar. They focus on pairing quality, New American fare with diverse wines, craft cocktails and hyper-local beer. They have a second location in Thornton Park adjacent to downtown Orlando.
 

Plant Street Market is anchored by Crooked Can Brewing Company. The acclaimed craft brewery’s creations are nicely complemented by the market’s array of dining options, including pizza, sushi, burgers and vegan fare, all of which can be enjoyed in Crooked Can’s taproom.

Other places on Plant Street to grab a drink or two (or three — you are on vacation, after all) include Pilars, a martini-focused piano bar with 1930s art-deco decor, and The Attic Door, a wine bar with live music. South of Plant Street but still in Winter Garden, New York Beer Project is a gastropub that celebrates New York City’s rich brewing history with a glorious recreation of the Atlantic Garden Beer Hall, circa 1892.
 

You will find numerous bespoke retailers in Winter Garden, particularly on Plant Street. Just 10 minutes away by car, Winter Garden Village is home to top national retailers, smaller shops and numerous dining options. And every Saturday, the Winter Garden Farmers Market is a great source for locally produced goods.

The Winter Garden Heritage Foundation operates two museums in Winter Garden, starting with the Winter Garden Heritage Museum. Inside, you will find photographs and memorabilia dating back to the pioneer days, Native American artifacts, and a citrus packing house replica. Outside, a caboose, a 1950s fire truck, and vintage tractors and equipment are available for interactive play.

Nearby, the Heritage Foundation’s Central Florida Railroad Museum is a must-visit for anyone with an interest in train travel. Artifacts here include a caboose, a velocipede handcar, a 1938 Fairmont motorcar and an extensive collection of dining car china and silver. Last but not least, stop by downtown Winter Garden’s SOBO Art Gallery & Studio, a historic building and former firehouse that hosts monthly exhibitions and events.
 

Throughout the year, Winter Garden hosts high-profile events that are free to attend for residents and visitors alike. These include July 4’s Party in the Park, October’s Halloween Fest and holiday events in December, among others. And every Friday night, you can enjoy free live music on Plant Street as part of the Fridays on the Plaza series. Use our Events Calendar to see what this popular district has on tap ahead of your next visit to Orlando.