The City of Winter Garden

Get to know the dining, culture and outdoor adventures that make the city of Winter Garden one of the Orlando area's most charming communities.

The Orlando area is packed with hidden-gem communities featuring unique dining, arts, shopping and entertainment, and Winter Garden is a prime example. Just 20 minutes north of Walt Disney World® Resort and 30 minutes west of downtown Orlando, it's a destination in its own right — one that serious foodies, art-lovers and outdoor enthusiasts will want to visit on their next trip to Orlando!

Getting to Know Winter Garden

Two women and a man walk down a sidewalk in downtown Winter Garden.
Plant Street in 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, which is listed on the National Registry of Historic Places.

Throughout the year, Winter Garden also 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.

Learn more: Orlando Events

Dining, Nightlife & Shopping in Winter Garden

Crooked Can Brewery seating area
Crooked Can Brewing Company in Winter Garden Near Orlando (Photo © Crooked Can Brewing Company)

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.

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.

Winter Garden has even more to offer when it comes to food, including Plant Street's Moon Cricket Grille, Thai Blossom Restaurant and Urban Flats. Just a short distance from Plant Street, you can enjoy the tastes of New Orleans at The Big Easy, get southern-style comfort food at Country House Restaurant, or dine on authentic Italian at Bella Italia Ristorante.

To play while you eat, head to GameTime — a family entertainment center with bowling, arcade games and more — in nearby Ocoee. That neighboring town is also home to one of two RusTeak Restaurant & Wine Bar locations, with the original being in Orlando's College Park neighborhood.

Learn more: Orlando's College Park District

Farmer's Market in downtown Winter Garden
Winter Garden Farmers Market

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.

Arts, Culture & Entertainment in Winter Garden

Central Florida Railroad Museum in downtown Winter Garden
Central Florida Railroad Museum in Winter Garden

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.

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.

Learn more: Orlando Train Rides

If you'd like a side of spooky with your history lessons, check out American Ghost Adventures, which offers walking tours of the community's supernatural side led by a knowledgeable paranormal investigator. (However, a minimum of four participants are needed to book a reservation.)

Garden Theater in downtown Winter Garden
Garden Theatre in Winter Garden

For performing arts, look no further than the Garden Theatre, which has been standing since 1935. It offers a robust schedule of live theater and concerts, as well as an eclectic lineup of films.

Last but not least, Winter Garden even has its own escape-style attraction, Escape Goat, which features three challenging rooms. And every Friday night, you can enjoy free live music on Plant Street as part of the Fridays on the Plaza series.

Sports, Recreation & Relaxation in Winter Garden

A single rider enjoys a stretch of canopied bike trail on the West Orange Trail
West Orange Trail in Winter Garden Near Orlando

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. And 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!

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 fishing and relaxing at Lake Apopka, as well as horseback riding at numerous equestrian operators in the area.

Cover photo courtesy Crooked Can Brewing Company.

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