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City of Winter Garden Holiday Events

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
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.
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.

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.

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