Winter Garden City Holiday Events

Winter Garden City Holiday Events

The Downtown Conservatory will be fun with a range of Tis the Season events from November 27 through the end of 2021. Events will include the Merry Winter Garden Light Show, Horse Drawn Holiday Carriage Tours, Holiday Moonlight Movie Community, Small Business Saturday Sidewalk Sale, and Holiday Boutique Stroll , And more.

Here are the upcoming Winter Garden holiday events:

Small business Saturday sidewalk sale
November 27
The whole day
Downtown Winter Garden
Outdoor sidewalk sale with special offers/promotions in a festive setting. Small-scale shopping day to help large businesses support local businesses.
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Moonlight Vacation movie
November 27
5:30 PM: Pre-show activities including face painting train ride. 7:10 pm: electrode articulation (G, 100 min)
Winter Garden Downtown Pavilion, 104 S. Lakeview Ave.
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Fun Winter Garden Light Show
4, 10, 11, 12, 17, 18, 19, 23 December
6:00 – 9:00 pm
300 W Plant Street – Downtown Winter Garden
Stunning holiday light show synchronized with music on the front facade of Winter Garden City Hall.

Horse drawn carriage tours
4, 10, 11, 17, 18, 19, 22, 23, 24, 26, 27, 28, 29, 30
5:30 PM – 9:30 PM
104 S. Lakeview Ave.
Experience a 20-minute tour through the enchanting winter wonderland of downtown Winter Garden.
Reservation / Required Fee

Holiday Boutique Stroll
December 9
5:00 – 8:00 pm
Downtown Winter Garden
Sips, snacks and sales at participating stores plus discounts on the outdoor sidewalk amid a festive wonderland.
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Very funny farmers market
4, 11 and 18 December
8:00 am – 1:00 pm
Winter Garden Downtown Pavilion, 104 S. Lakeview Ave.
Shop for unique gifts, holiday decorations, and seasonal food at the Holiday Market.

Eid music at Fridays on the Plaza
10, 17 December
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 who perform favorite holiday tunes.

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