Downtown Winter Garden

Small Town Charm

Places to Shop

Dining and Drinks

Arts and Entertainment

Farmers Market

History and Museums

Upcoming Events

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

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

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

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

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

“Dog Days of Summer: The Ulti-Mutt Art Exhibit”

July 6, 2026
5:30 pm
Winter Garden City Hall, Art in Public Places Gallery, 300 W. Plant Street

Created by local artists responding to the City of Winter Garden Artists’ Call, the juried show displays original artwork to celebrate their favorite pooch. Your pup can be part of the exhibit too - bring a max. 4” X 6” photo to add to “The Dogs of Winter Garden” art piece, a visual display of our canine residents. Pups also welcome inside City Hall to view this paws-itively incredible exhibit!

“Dog Days of Summer: The Ulti-Mutt Art Exhibit”

July 7, 2026
7:30 am - 5:30 pm
Winter Garden City Hall, Art in Public Places Gallery, 300 W. Plant Street

How to Train Your Dragon (Live Action)(PG)

July 7, 2026
10:00 am
Garden Theatre on Plant, 160 W Plant Street, Winter Garden, FL 34787

Enjoy your favorite FLIX for $5.00 EVERY TUESDAY all summer long (June 9 - August 4) at the iconic Garden Theatre on Plant! Summer Flix at the Garden features kids' matinees (10:00 am and 2:00 pm) as well as evening screenings (7:00 pm) of classic and contemporary hits. Hosted by the City of Winter Garden, all tickets are $5.00 (no added fees or tax), providing a fun, budget-friendly (and air conditioned) summer activity for the community. Tickets (assigned seating) are available for online purchase only (no box office). Online ticket sales remain open until 30 minutes after the movie start time. All tickets are final sale and nonrefundable. The Theatre is a cashless venue (only card payment accepted).