The City of Winter Garden

Nestled on the banks of Lake Apopka, and not to be confused with Winter Park to the north of downtown Orlando, Winter Garden is like many Central Florida communities in that its history is firmly tied to Florida’s citrus roots and rail travel. Today, it’s a robust city built around small businesses and a thriving downtown area that’s centered around Plant Street and listed on the National Registry of Historic Places.

Discover: Orlando History

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.

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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.

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.

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Other places on Plant Street to grab a drink or two (or three — you’re on vacation, who’s counting?) include Pilars, a martini-focused piano bar with 1930s art-deco décor, 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.

Winter Garden has even more to offer when it comes to food, including 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.

You'll also find a number of 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.

For performing arts in Winter Garden, look no further than the Garden Theatre, which has been standing since 1935 and offers a robust schedule of live theater, concerts and films. You can also check out American Ghost Adventures, which offers walking tours of the community’s supernatural side led by a knowledgeable paranormal investigator — including a stop at the Garden Theatre. (A minimum of four participants are needed to book a reservation.)

The Winter Garden Heritage Foundation operates two museums in Winter Garden, starting with the Winter Garden Heritage Museum. Inside, you’ll 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.

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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.

Discover: Orlando Train Rides

For nature enthusiasts, the most compelling reason to come to Winter Garden is the West Orange Trail. Stretching from Winter Garden to Apopka in the north, the paved, 20.8-mile trail is perfect for biking and hiking, and access is free. If you’re traveling with kids, you'll be glad to know that the trail has playground equipment and other amenities. It also got Winter Garden recognized as an official Florida Trail Town.

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If you didn’t bring bicycles with you, you can rent them from Winter Garden’s West Orange Trail Bikes & Blades Co., which also has bikes for kids, as well as trailers for children who are too young to pedal. Tour packages are also available, and they’ll even deliver to your hotel at an additional cost.

Other outdoor activities in Winter Garden include birding, fishing and relaxing at Lake Apopka, as well as horseback riding at numerous equestrian operators in the area. Given everything else the area has to offer, you’ll definitely want to make time for Winter Garden during your next Orlando getaway.