Downtown Winter Garden will be merry with a line-up of Tis the Season events from November 27th through the end of 2021. Events will include A Merry Winter Garden Light Show, Horse Drawn Holiday Carriage Tours, a community Holiday Moonlight Movie, Small Business Saturday Sidewalk Sale, a Holiday Boutique Stroll, and more.
Here are the upcoming holiday events in Winter Garden:
Small Business Saturday Sidewalk Sale
November 27
All-Day
Downtown Winter Garden
Outdoor sidewalk sale with special offers/promotions in festive surroundings. A day to shop small to help big to support local-owned businesses.
Learn more
Holiday Moonlight Movie
November 27
5:30 pm: Preshow activities including a train ride for tots and face painting. 7:10 pm: The Polar Express (G, 100 minutes)
Winter Garden Downtown Pavilion, 104 S. Lakeview Ave.
Free
Learn more
A Merry Winter Garden Light Show
December 4, 10, 11, 12, 17, 18, 19, 23
6:00 – 9:00 pm
300 W. Plant St., Downtown Winter Garden
Spectacular holiday light show synchronized to music projected onto the front façade of Winter Garden City Hall.
Free
Horse Drawn Holiday Carriage Tours
December 4, 10, 11, 17, 18, 19, 22, 23, 24, 26, 27, 28, 29, 30
5:30 pm – 9:30 pm
104 S. Lakeview Ave.
20-minute tour experience through the enchanted winter wonderland of downtown Winter Garden.
Reservations/fee required
Holiday Boutique Stroll
December 9
5:00 – 8:00 pm
Downtown Winter Garden
Sips, snacks, & sales at participating shops plus an outdoor sidewalk sale amidst a festive wonderland.
Learn more
A Very Merry Farmers Market
December 4, 11, 18
8:00 am – 1:00 pm
Winter Garden Downtown Pavilion, 104 S. Lakeview Ave.
Shop for unique gifts, holiday décor, and seasonal food in the festive market.
Holiday Music at Friday’s on the Plaza
December 10, 17
7:00 pm – 9:00 pm
December 10 – Juniper Club
December 17 – The Caroling Company
Centennial Plaza Gazebo, Downtown Winter Garden
Line up of talented musicians performing favorite holiday tunes.
Free
