Hosted by the City of Winter Garden, the Winter Garden Christmas Parade is a free community event. Bring a lawn chair or blanket and head to your favorite spot for this annual holiday event. A long-standing Winter Garden holiday tradition will delight spectators and bring in holiday cheer! Do not forget to look for the Big Guy himself at the end of the parade! The Winter Garden Christmas Parade kicks off at 10:00 am on Dillard Street at the Palmetto Street intersection (by Wells Fargo) proceeds north on Dillard Street, then heads west/left on Plant Street through historic downtown and concludes at Park Avenue.