city of winter garden

NOV. 30 – DEC. 27

‘Tis the Season Events:

NOVEMBER 16, 11 AM-11 PM

3rd Annual Central Florida American Legion -Challenge 22 Suicide Awareness Event:

Join the Winter Garden American Legion Post 63, in partnership with Crooked Can Brewery, for a walk, block party, and day of camaraderie. The event starts at 11 am with an opening ceremony, followed by a 2.2-mile walk at 12 pm that will close Central Ave next to the Plant Street Market. There will be no impact/closures on Downtown Plant Street. From 1 pm-11 pm will be a Celebration of Veterans and Music Festival. In addition, there will be a mini-replica of the Vietnam Wall and the Global War on Terrorism Wall displayed inside the American Legion Post for the public to visit.  Open to the public and free! For more information, visit


NOV. 30, 10:00 am-7:00 pm


Shop Local Winter Garden Small Business Saturday Event:

NEW -- please see this year’s poster, including music schedule!  Day-long event in downtown with live music, raffles, and special discount offers to kick-off the holiday shopping season. If you would like to be included in marketing campaign, please submit your business’ special sale offer and or raffle prize to  this week as campaign will commence very shortly.

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December  4th

Light-Up Winter Garden


December  5th

DownTown -Holiday Parade