The 2023 Holiday Guide is here! Winter Garden & surrounding communities has many safe and festive activities for people of all ages to enjoy.
Check back for new events being added daily!
All events are tentative please visit event details for updates.
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Moonshine & Mistletoe
Multiple Dates
Nov 24 - Dec 23
Garden Theatre
160 W Plant St
Winter Garden, FL 34787
In the midst of the Great Depression, they have no gifts to exchange, but instead, they share their love of Appalachian hymns and carol.
Holiday Market
Dec 2
1PM - 4PM
Downtown Winter Garden
Shopping fun at participating downtown Winter Garden shops! Holiday goods and treats, Dickens Carolers, take-home Caricatures, Holiday Story Time & more!
Learn More
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Street Holiday Entertainment
Multiple Dates
Dec 1, 2, 15, 16, 22, 23
6PM - 9PM
Downtown Winter Garden
Be on the look out for strolling performers & live entertainment throughout downtown Winter Garden.
Holiday Horse Drawn Carriage Tours
Multiple Dates
6PM - 9PM
Dec 3, 10, 12, 14, 17-21, 26-28
Downtown Pavilion
104 S. Lakeview Ave
Winter Garden, FL 34787
Experience the magic of the holiday season with a private horse drawn carriage tour through Historic Downtown Winter Garden.
Spirits and Sparkles
Dec 12
5 to 8 pm
Downtown Winter Garden Merchants
Late night shopping, refreshments & holiday fun at select locations downtown.
Light Up
Winter Garden
Dec 1
6 - 9 PM
Downtown Winter Garden
Join us for the momentous flipping of the switch to turn on the holiday lights and watch downtown glow. Enjoy holiday activities and entertainment.
Winter Garden Golf
Cart Parade
Dec 2
6PM - 7PM
Downtown Winter Garden
Junior Service League and the CITY OF WINTER GARDEN will host the 11th Annual WG Christmas Golf Cart Parade.
Fridays on the Plaza Holiday Music
Multiple Dates
7PM - 9PM
Downtown Winter Garden
Centennial Plaza Gazebo
Dec 1- Light Up Winter Garden
Dec 8- Roots & Rosin
Dec 15- Paint it Black Quartet
Dec 22- Safia Valines Trio
Dec 29- Gilly and the Girl
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Chanukah Celebration & Menorah Lighting
Dec 7
TBD
Downtown Winter Garden
Butterfly Sculpture Park
Christmas Carnival
Dec 16
10AM - 2PM
Matthew's Hope
611 Business Park Blvd
Winter Garden, FL 34787
Jingle all the way to our Magical Christmas Carnival! Meet Santa Claus, visit the toy workshop, Carnival fun, Sweet treats, live entertainment, and more!
Everyone is welcome to join!
Struggling families looking to participate and receive help with toys, please call or email!
407-905-9500
info@matthewshopeministries.org
Winter Garden Christmas Parade
Dec 2
10AM
Kick off from S. Dillard St & E. Plant St.
Bring a lawn chair or blanket to your favorite spot for this annual holiday event.
A Very Merry
Farmers Market
Multiple Dates
Dec 2, 9, 16, 30
8AM - 1PM
Downtown Pavilion
104 S. Lakeview Ave
Winter Garden, FL 34787
This festive-decorated market is ideal for shopping for gifts, seasonal decor, as well as fresh product and artisan foods for your holiday celebrations.
A very merry Santa will be visiting Dec 9 & 16th 9 AM - 12PM at the parking garage plaza.
A Merry Winter Garden Light Show
Multiple Dates
6PM - 9PM
Dec 2, 3, 8-10, 15-17, 22, 23
City Hall
300 W. Plant Street
Winter Garden, FL 34787
This annual animated holiday light extravaganaza is a town tradition!
Christmas Spectacular
Dec 9
6PM - 9PM
Gymnastic USA
13175 W. Colonial Dr
Winter Garden FL, 34787
Gymnastics USA is partnered with We Are Winter Garden to bring the community a night of Food Trucks, Santa Visit, WHOLE Family Open Gym, Winter Garden Vendors, Rock Climbing, DJ Music, Raffles & Prizes, Winter Garden Swag, Snow Fall, CHRISTMAS, and More!
Registration is required to enter. Get your free tickets on the Winter Garden App.