Family enjoying a day of shopping in Winter Garden

Shopping Downtown

Stroll up and down the streets of Historic Downtown Winter Garden and enjoy the one of a kind shops that make Winter Garden an unforgettable experience. No matter what you are looking for, there is a place for you. Bring home a piece of our small-town charm.

View Shops

Chicken and Bacon Sandwich

Chow Downtown

While taking in the small-town charm as you explore Downtown Winter Garden, make sure to stop in and experience the wonders of our award-winning restaurants.

Foodies Paradise Here

Winter Garden Farmers Market

Discover Fresh Picks at the Farmers Market

Repeatedly voted the best Farmers Market state- and nation-wide, the Market offers a large selection of vendors from locally grown produce, baked goods, specialty foods, to homemade soaps, artisan creations, fresh flowers, and so much more!

Get Pickin'

Arts and Entertainment Collage

Arts and Entertainment

Beyond one of kind shops, award-winning dining experiences, and unforgettable events... Downtown Winter Garden is also home to an underswell of arts, culture, and creativity.

Culture this way

Winter Garden History Center

Make History in Downtown Winter Garden

Looking to know more about this charming little city with a juicy past? Visit one of the historic museums located right in the heart of Downtown. Plan a moment of your day to learn how Winter Garden has become a successful example of historic preservation.

Explore History

Children Playing in the Downtown Interactive Fountain

Make Time for a Whole Lot of Fun

Whether seeking adventure and new discoveries, or longing to unwind and relax surrounded by historic charm, Downtown Winter Garden has something for everyone. The enchanting small town authenticity turns back time and truly feels like a getaway.

Places to Play

Events You Won't Want to Miss

Garden Theatre - Raisin in the Sun

Garden Theatre Play: A Raisin in the Sun

March 3, 2021
7:30 pm
Garden Theatre 160 West Plant Street

Shop, Dine and Stroll

Shop, Dine & Stroll

March 27, 2021
9:00 am - 9:00 pm
Downtown Winter Garden

In celebration of National Mom and Pop Business Owners Day come shop, dine & stroll Downtown Winter Garden. There will be a sidewalk sale, spacious outdoor dining, plus the farmers market! Many boutiques will be selling spring fashions & merchandise while our restaurants will be having seasonal menus.

Garden Theatre Interactive Movies - Spaceballs

Spaceballs playing at Garden Theatre

March 28, 2021
7:30 pm
160 W Plant Street

Art Exhibition “The World Outside” Opening Reception

April 1, 2021
5:30 pm - 8:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio 127 S. Boyd Street

See All Events
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