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

Music in Pilars Loft

April 2, 2021

146 W Plant St.

Arts in April

April 17, 2021
8:00 am - 11:00 pm
Downtown Winter Garden

April 17th will be a day-long celebration of the arts featuring kids’ art activities, community canvas display, sidewalk chalk art, plein air, scavenger hunt and more. All leading up to the evening fundraising event "Art Night VIP."

Art Night VIP

April 17, 2021
6:00 pm - 9:00 pm
Downtown Winter Garden

In the evening, downtown will be aglow with color and art with the first-ever “Art Night VIP” fundraising event to help support the arts. “Behind The Velvet Rope” VIP Access to Curated Immersive Art Experiences in several small COVID-safe boutique settings around historic Downtown Winter Garden.  There will be pop-up art on the streets bringing life and creativity to our Downtown. Tickets are limited so secure your spot!

Garden Theater Play: Godspell

April 22, 2021
7:30 pm
Garden Theater 160 West Plant Street

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