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The 2024 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.
Light Up
Winter Garden
Dec 6
6 - 9 PM
tree lighting at 6:16PM
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.
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Holiday Street Performers
6 - 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
5:30 - 8:30PM
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.
Orlando Korea Festival
Dec 7
10AM - 4PM
7000 Winegard Rd
Orlando, FL 32809
Experience the best of Korean culture with authentic food, unique vendors, traditional games, K-pop and cultural performances, and a Hanbok experience. Free admission for a day of fun and celebration!
Chanukah Celebration & Menorah Lighting
Dec 7
6PM
Downtown Winter Garden
Butterfly Sculpture Park
Grand Menorah Lighting at 6PM followed by a live band, Jewish Unity. Enjoy an animal show, hot latkes, chanukah trinkets, cotton candy, crafts for kids, and more!
Santa Golf Cart Parade
Dec 8
3 - 4:30PM
Stoneybrook West Golf Club
15501 Towne Common Blvd
Winter Garden, FL
Annual Santa Golf Cart Parade. Rentals available. Storytime with Santa, bounce house, and more! Open to the Public!!
Holiday Opera
Dec 14 & 21
at the Garden
160 W Plant Street
Winter Garden, FL
Holiday Opera at the Garden staring World-Class Operatic Soprano Samar Salame Hawat.
Christmas Spectacular
Dec 14
Gymnastic USA
13175 W. Colonial Dr
Winter Garden FL, 34787
Gymnastics USA 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.
Christmas in the Garden
Dec 6
6 PM
Downtown First Baptist
125 E Plant St
Winter Garden, FL
Join us for the annual Christmas in the Garden big band extravaganza.
A Merry Winter Garden Light Show
Multiple Dates
6 - 9PM
Dec 6, 7, 8, 13, 14, 15, 20, 21, 22
Winter Garden City Hall
300 W. Plant Street
Winter Garden, FL 34787
This annual animated holiday light extravaganza is a town tradition!
Learn More
A Very Merry
Farmers Market
Multiple Dates
Dec 7, 14, 21
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 14th & 21st 9 AM - 12PM.
The Winter Garden Polar Express
Dec 7
12 - 2PM
Kick off from S. Dillard St & E. Plant St.
Welcome aboard the Winter Garden Polar Express! Join us for a magical journey at the Winter Garden Heritage Foundation Train and explore various local shops along the way. Get ready for a festive experience filled with holiday cheer. All aboard!
Winter Garden Golf
Cart Parade
Dec 7
6 - 7PM
Downtown Winter Garden
Junior Service League and the CITY OF WINTER GARDEN will host the 12th Annual WG Christmas Golf Cart Parade.
Gingerbread House Workshop
Dec 8
3 - 4:30PM
SOBO Winter Garden
Build a gingerbread house w/step by step instruction. $52 per house.
Tinsel Tone & Holiday Glow
Dec 12
Family Medicine Institute
15532 West Colonial Dr
Winter Garden, FL
Join us for a festive afternoon filled with holiday vibes, sparkling sips, tasty treats, and exclusive mini treatments! You’ll also enjoy special event pricing, thrilling giveaways, and a chance to try out The Emsculpt Neo and Alastin Skincare.
Reindeer Run
December 21, 2024
SeaWorld Orlando
Bring the family out for the best Holiday Fun Run in the area. Run or walk the festive 3 mile route through SeaWorld to the sound of holiday bells and finish in a Runner wonderland with holiday treats for all finishers!
Together with WFTV - 9 Family Connection, Track Shack supports Toys for Tots.
Dash away to https://www.trackshack.com/event/236 for more information and to register
Boozy Book Fair & Market
Dec 6
6 - 9 PM
Home State Brewing Co.
Winter Garden, FL
Stroll through 15+ vendors for unique holiday finds, explore the book fair by White Rose Book Shop on the patio, meet local authors, & enjoy live music by Francesca in the Biergarten.
Fridays on the Plaza Holiday Music
Fridays
7 - 9PM
Downtown Winter Garden
Centennial Plaza Gazebo
Dec 6- Light Up Winter Garden
Dec 13- Juniper Club
Dec 20- Safia Valines Quartet
Dec 27- L & G Live
Winter Garden Christmas Parade
Dec 7
10 - 11AM
Kick off from S. Dillard St & E. Plant St.
Bring a lawn chair or blanket to your favorite spot for this annual holiday event.
Santa's Lane
Dec 7
3 - 6PM
220 N. Tubb St
Oakland, FL
Come revel in small-town charm and the spirit of the season with these memorable experiences:
*Shop in the Christmas Village, coordinated by Orange Blossom Market Co.
*Tube down the inflatable Alpine snow slide
*Indulge in tasty treats
*Write letters to Santa
*Vote for your favorite tree
*Enjoy a festive Golf Cart Parade
*Take your photos with Santa and his elves
And More!
Holiday Night Market
Dec 7
4 - 8PM
Downtown Winter Garden
A new free event for 2024, the Holiday Night Market transforms the Downtown Pavilion area to a picturesque festive open-air market bustling with market stalls of vendor booths of holiday goods for sale such as décor, unique gifts, festive treats and beverages, and more.
Holiday Flix
Dec 10, 11, 17, & 18
at the Garden
160 W Plant Street
Winter Garden, FL
The City of Winter Garden presents Holiday Flix at the Garden. These holiday classic movies appeal to all ages and conjure past holiday memories -- and help to create new ones. See these festive flix in the timeless ambiance of the Garden Theatre while visiting the Holiday Wonderland in 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.
Santa's Twilight 5k
December 21, 2024
Clermont Historic Downtown
A festive holiday night run/walk through Historic Downtown Clermont and along the beautiful Clermont waterfront.
Super cool finisher medal and long-sleeve shirt, chip timing, glow necklaces, costume prizes, and hot chocolate, and cookies will be waiting for you after you finish!