Situated just west of Orlando, the city of Winter Garden, Florida is perhaps best known for its close proximity to some of the most popular theme parks in the country. Once full of citrus farms, Winter Garden offers old Florida-style, charm, and several things to do in its own right. For visitors interested in sampling some of the local craft beer, the Crooked Can Brewing Company is worth a visit, while history buffs can explore the numerous items on display at the Winter Garden Heritage Museum. There’s also theatrical performances to watch and artwork to browse in town as well. Hours/availability may have changed.


1.Crooked Can Brewing Company, Winter Garden, Florida

Crooked Can Brewing Company, Winter Garden, Florida
© Crooked Can Brewing Company

The Crooked Can Brewing Company offers a great way to end a long day in the Florida sunshine with a cold, refreshing craft beer, brewed locally using natural ingredients. Located in Winter Garden, Florida on West Plant Street, this craft brewery is a popular spot among locals in the greater Orlando area thanks to its brews, helpful staff, and relaxed environment. Samplers of the Crooked Can Brewing Company beers are available and visitors can also dine on some tasty food while they enjoy their beer thanks to a menu that includes wings and burgers. Tours of the brewery are offered as well.

426 W Plant St, Winter Garden, FL 34787, Phone: 407-395-9520

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2.Garden Theatre, Winter Garden, Florida

Garden Theatre, Winter Garden, Florida
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The Garden Theatre is the professional performing arts center of West Orange County, hosting movies, concerts, plays, and more to the community of Winter Garden and the surrounding area. Originally constructed back in 1935, the then single-screen cinema was the first theater built for “talkies” in Central Florida and served as a local gathering place for watching the latest films and newsreels of the time. Today, the Garden Theatre in Winter Garden is a professional, nonprofit organization that presents more than 650 events every year and aims to enrich, engage, and entertain people of all ages through creative experiences.

160 W Plant St, Winter Garden, FL 34787, Phone: 407-877-4736

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3.Things to Do in Winter Garden, Florida: Winter Garden Heritage Museum

Things to Do in Winter Garden, Florida: Winter Garden Heritage Museum
© Winter Garden Heritage Museum

The Winter Garden Heritage Foundation operates two museums in Winter Garden: the Central Florida Railroad Museum and the Winter Garden Heritage Museum. Both of these museums are open daily, with the exception of major holidays, and are free to the public. The Winter Garden Heritage Museum was established in 1998 and preserves the heritage behind the small-town charm of Winter Garden, including the inventions and architecture of the city’s past. Located in the middle of downtown, the museum is housed inside the old Atlantic Coast Line Depot, which dates back to 1918, and features a wide array of items on display.

1 N Main St, Winter Garden, FL 34787, Phone: 407-656-3244

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4.Things to Do in Winter Garden, Florida: Winter Garden Art Association

Things to Do in Winter Garden, Florida: Winter Garden Art Association
© Winter Garden Art Association


The Winter Garden Art Association serves as a community center in downtown Winter Garden, Florida for the visual arts. With a mission of encouraging artistic expression and individual creativity, promoting community involvement, and advancing art education and appreciation, the art association hosts art workshops and themed art exhibits that change on a monthly basis. The Winter Garden Art Association operates the SOBO Art Gallery, open Tuesday to Saturday from 10:00am until 6:00pm, which presents monthly art exhibitions featuring Central Florida artists. An opening reception for each exhibition takes place on the first Thursday of that month’s Exhibition.

127 S Boyd St, Winter Garden, FL 34787, Phone: 407-347-7996

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4 Best Things to Do in Winter Garden, Florida



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