- December 4, 2025
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Orlando Gentlemen of Jazz play the first night of downtown Winter Garden's Halloween Experience 2021 on Friday, Oct. 22.
Characters and performers roam Plant Street for photo ops.
The Halloween Light Show on City Hall projects a variety of spooky scenes onto the iconic building.
Colorful skeletons dance with scarecrows.
Pumpkins seem to fill the building in this animated scene.
Giant spiders crawl across the facade.
Guests walk, and sometimes run, through the hay maze by City Hall.
An animatronic dragon welcomes visitors.
The fun and frights last through Halloween night.
Ghosts and black cats seem to follow you, but they just stick around for the next guest.
There are several cute scenes throughout the maze.
This is actually the exit, so you should keep out of this end.
Visitors stroll through lighted streets.
The moon shines through the lighted branches along Plant Street.
Plantation Jewelers, at 15 W Plant St., features some impressive decor.
A detailed jewelry arrangement takes center stage in the window display.
Headstones backdrop the bling.
The spooky season has arrived on Plant Street as downtown Winter Garden is decked out with tricks and treats. Halloween Experience 2021 began Friday, Oct. 22, with live music, a hay maze and a projection show that makes City Hall look like the scariest place in town.
Events continue through Oct. 31, click here for the full schedule.
