10-Day Halloween Experience in Downtown

Downtown Winter Garden has turned into a spooky setting to bring a 10-day Halloween Experience to residents and visitors. After all, why should Halloween fun only last one night! Complimentary “frightening” family-friendly festivities will include animated light shows, pop-up street performers, live music, an outdoor movie, a hay maze, fall-themed photo stations, decorations, light displays, a sidewalk sale, and so much more! The Winter Garden Halloween Experience will take place October 22-31, 2021, and its activities and décor will delight all ages.


Someone grab the fly swatter because gigantic bugs have invaded City Hall! The building’s walls are a canvas for a projection animated Halloween Light Show full of creepy crawlers and holiday icons. The 15-minute show runs in a continuous loop from 7-9 p.m. on Fridays/Saturdays/Sundays (October 22, 23, 24, 29, 30, 31). Winter Garden City Hall is located at 300 W. Plant Street.


You never know what may be prowling around downtown during the weekend nights of Halloween Experience, but it is bound to be entertaining! From 6-9 p.m. on Fridays/Saturdays/Sundays (October 22, 23, 24, 29, 30, 31), there will be pop-up street performers scouring the brick-lined streets. From live music and variety shows to jugglers, you just never know what you may stumble across for some surprise amusement.


Grab some blankets and chairs and get cozy to watch a Moonlight Movie under the stars! The City is presenting Monsters University (2013, G) to the community on Saturday, October 23. Showtime is at 7:10 p.m. but come early for the preshow activities starting at 6:30 p.m. Gather friends and family and meet at the outdoor Downtown Pavilion, 104 S. Lakeview Avenue.


What better way to shop than surrounded by Halloween decorations and festivities! The shops of Historic Downtown are hosting a daylong Harvest Sidewalk Sale & Stroll on Saturday, October 23. The cooler weather and festive surroundings make it the perfect day to shop the outdoor racks of sale and seasonal merchandise. With the holidays quickly approaching, it is a great opportunity to get a head start on gift buying.

The unique shops of downtown feature apparel, jewelry, home décor and greenery, cycling/running/sporting equipment and accessories, gourmet foods, health and beauty products, pet supplies, furniture, and much more. Extend your shopping up the road to the Winter Garden Library that is also participating (10:00 am-3:00 pm) with an outdoor sidewalk sale of a selection of books, movies, music CDs and more.

In addition, a number of downtown restaurants will feature seasonal menus and promotions to enjoy while dining at the outdoor patios surrounded by Halloween fun. What’s more, the City has declared the month of October as Outdoor Dining Month so grab a seat and something to eat next to the Halloween décor to take part. Remember to stay into the evening for the outdoor Moonlight Movie at the Downtown Pavilion for some more fun.


This caboose looks unsuspecting, but there is something lurking inside! For those that dare, take a stroll through the haunted caboose to find out what awaits. The level of spookiness is appropriate for children and is a fun background for photos. The Spooky Caboose will be available on Friday, October 29, from 3-8 p.m. outside the Winter Garden History Center, 21 E. Plant Street. Free, but donations are welcome to support the Winter Garden Heritage Foundation.


If you are looking for pumpkins to carve this Halloween, then the Winter Garden Farmers Market is your place to go! Pumpkins galore all of shapes and sizes including gargantuan make for fun choosing, as well as a backdrop for cute photos. A vast selection of odd-shaped gourds and fall produce perfect for your cornucopia can also be found at the market. With fresh vegetables and fruits from a bountiful fall harvest as well as seasonal décor available, fall is the perfect time for a trip to the outdoor market. With all that there is to do, plan to stay a while since the market recently expanded to more than 100 vendors and has added a new Kidz Zone and an Arts Market, as well as family-fun games on the lawn and live music. Open every Saturday from 8 a.m.-1 p.m. at the Downtown Pavilion, 104 S. Lakeview Avenue.


A hay maze is synonymous with fall, and the Winter Garden does not disappoint with its annual community hay maze! Located outside the front entrance of City Hall (300 W. Plant Street), a fall-decorated winding maze will delight all ages. The hay maze is open continuously from October 22-November 6.

Besides the hay maze, a number of elaborately decorated Halloween- and fall-themed photo stations throughout downtown make the perfect backdrop for photographs and social posts. What a great way to capture fall family fun to share with others and as a keepsake.


The historic Garden Theatre will be showing the timeless The Rocky Horror Picture Show (1975, R) twice on Halloween weekend: Saturday, October 30, at 10 p.m. and Sunday, October 31, at 8 p.m. Seats for this interactive movie are $15 and pre-show entertainment that you won’t want to miss starts 30 minutes prior to show time. Garden Theatre is located in the center of downtown at 160 W. Plant Street. Click here to purchase tickets.


Halloween Light Show on City Hall, 7:00-9:00 pm
Live Music, Shows, and Pop-up Street Performers, 6:00-9:00 pm

Harvest Sidewalk Sale & Stroll Downtown, All Day
Fall Themed Farmers Market, 8:00 am to 1:00 pm
Live Music, Shows, and Pop-up Street Performers, 6:00-9:00 pm
Moonlight Movie – Monsters University (2013, G)
Family Activities, 6:30pm/Movie 7:10pm
Halloween Light Show on City Hall, 7:00-9:00 pm

Live Music, Shows, and Pop-up Street Performers, 6:00-9 00 pm
Halloween Light Show on City Hall, 7:00-9:00 pm

Live Music, Shows, and Pop-up Street Performers, 6:00-9:00 pm
Halloween Light Show on City Hall, 7:00-9:00 pm
Spooky Caboose at the History Center, 3:00-8:00 pm

Fall Themed Farmers Market, 8:00 am-1:00 pm
Live Music, Shows, and Pop-up Street Performers, 6:00-9:00 pm
Halloween Light Show on City Hall, 7:00-9:00 pm
Interactive Movie at the Garden Theatre, Rocky Horror Picture Show (1975, R)
Preshow, 9:30 pm/Movie 10:00 pm/Click here to purchase tickets.

Live Music, Shows, and Pop-up Street Performers, 6 to 9 pm
Halloween Light Show on City Hall, 7 to 9 pm
Rocky Horror Picture Show (1975, R)
Preshow, 7:30 pm/Movie 8:00 pm/Click here to purchase tickets.

Hay Maze at City Hall
Seasonal-Themed Photo Stations
Halloween Decorations & Light Displays
Fall-Themed Merchandise, Food and Drinks
Expanded Patios amidst Halloween Experience and perfect for celebrating Outdoor Dining Month

All Halloween Experience events are complimentary except for the Garden Theatre movies. Click here for more upcoming Downtown Winter Garden events.

The 10-day Winter Garden Halloween Experience is part of the “Living Local” campaign sponsored by the City of Winter Garden to encourage exploring and enjoying one’s hometown while supporting its local businesses.


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