Historic Downtown Winter Garden
October 20 – October 31, 2023

Halloween is celebrated for 12 days – not just one — in Winter Garden! The City’s annual Halloween Experience provides family-friendly festivities in Downtown Winter Garden, including seven nights of an outdoor animated Halloween Light Show on City Hall; a hay maze; fall- and spooky-themed photo locations, decorations and light displays throughout downtown; a Spooky Caboose at the Winter Garden Heritage Museum; a Halloween Celebration at the fall-themed Farmers Market, and more! Costumes are welcome any day!

 AVAILABLE ALL-DAY, EVERY DAY

• Hay Maze at City Hall (10:00 am – 9:00 pm)
• Halloween- and Fall-Themed Photo Stations 
• Seasonal Decorations & Light Displays throughout Downtown
• Unique Stores & Restaurants to Shop, Dine & Stroll surrounded by historic charm and spooky and fall ambiance
• Expanded Outdoor Patios to dine amidst the Halloween Experience while enjoying the crisp autumn weather

SCHEDULE & DESCRIPTION OF SPECIAL EVENTS

All events and activities are FREE, unless noted otherwise.

HALLOWEEN LIGHT SHOW

A Halloween animated light show synchronized to music projected onto the front façade of City Hall.

October 20, 21, 22, 27, 28, 29, 31 | 7:00 – 9:00 pm
City Hall, 300 W. Plant Street | Free

STREET PERFORMANCES & SURPRISES

A variety of outdoor street performers will delight audiences as visitors stroll, shop, and dine. You just never know what pop-up surprises await!

October 20, 21, 22, 27, 28, 29, 31 | 6:00 – 9:00 pm
Historic Downtown  | Free

HALLOWEEN SPOOKTACULAR PRESCHOOL HOLIDAY PROGRAM

Hosted by the City of Winter Garden Parks & Recreation Department, preschoolers are invited to enjoy fall carnival games while dressed in your spookiest costume. Finish the morning off with holiday themed craft and office trick or treating! Welcome to bring a friend or a group to this free event. 

Friday, October 27 | 10:00 am – 12:00 pm
Ages: 3 – 5 years old
All preschoolers welcome! Preschool Classes are also invited, but first please send email to recinfor@cwgdn.com for participation information.
Jessie Brock Community Center, 310 N. Dillard Street | Free

HALLOWEEN CELEBRATION AT WINTER GARDEN FARMERS MARKET

Come out to the market for some Halloween fun! Children can make a special Halloween craft to take home at the KidZone tent (at Parking Garage Plaza on Tremaine Street). The fall-decorated market will also feature live music and family-friendly games on the lawn adjacent to the Pavilion.

Pumpkin, pumpkins, and more pumpkins — of all shapes and sizes – can be found at the Farmers Market. Get your gourds, fresh fall harvest produce, seasonal décor, and lots of treats to make your Halloween and fall holidays special. The pumpkin display is great photo op too for your fall pictures!

Saturday, October 29
Market Hours, 8:00 am – 1:00 pm |  Free Event Activities, 9:00 am – 12:00 pm
Downtown Pavilion, 104. S. Lakeview Ave

COMMUNITY PARTNERS’ EVENTS:

DESCENT INTO MADNESS DINNER THEATRE SHOW

Join us for an intimate, yet disturbing, evening of dinner, theatre and a few classic horror stories with a twist as we journey inside the mind of a madman. Presented by the Winter Garden Masonic Lodge #165, Descent into Madness is a dark, intense drama. Limited seating available.

Friday, October 13
Saturday, October 14
Sunday, October 15

Doors Open at 7:00 pm  |  $25 per ticket, Click here to purchase tickets.
Winter Garden Masonic Lodge, 230 W. Bay Street

LEGO DAY AT THE RAILROAD MUSEUM — A Frightfully Fun Experience

Stop by the Central Florida Railroad Museum as they host the Greater Florida Lego User Group and their large Lego display loaded with buildings, people, trains, and a Halloween surprise! A kids’ coloring table and sweet treats will be available for the visiting little ghouls.

Saturday, October 21  | 9:00 am – 4:00 pm | Free
Central Florida Railroad Museum, 101 S. Boyd Street 

CREATE A HAUNTED HOUSE FAMILY EVENT AT SOBO ART GALLERY

You will be amazed as you work together to transfer a prepared cereal box on a base into an awesome “Haunted House.” All materials and step-by-step guidance are provided. This popular family event fills up quickly! $30 fee for 1 adult/1 child. Questions, call 407-347-7996.

Saturday, October 21 | 4:00 – 5:30 pm
$30 per house for 1 adult with 1 child | Fee & reservation required. Click here to register (limited spots available).
SOBO Art Gallery, 127 S. Boyd Street 

SPOOKY CABOOSE AT THE WINTER GARDEN HERITAGE MUSEUM

Enter the Spooky Caboose – if you dare — stationed outside the Winter Garden Heritage Museum. The spooky-decorated caboose has fun frights for all ages. 

Monday, October 31 | 3:00 – 8:00 pm | Free to Enter, Donations Appreciated
Winter Garden Heritage Museum, 1 N. Main Street  

DAILY HALLOWEEN EXPERIENCE SPECIAL EVENTS SCHEDULE

FRIDAY, OCTOBER 13
Descent into Madness Dinner Theatre Show, 7:00 pm, presented by the Winter Garden Masonic Lodge. Purchase Tickets (fee required/limited spots available)

SATURDAY, OCTOBER 14
Descent into Madness Dinner Theatre Show, 7:00 pm, presented by the Winter Garden Masonic Lodge. Purchase Tickets (fee required/limited spots available)

SUNDAY, OCTOBER 15
Descent into Madness Dinner Theatre Show, 7:00 pm, presented by the Winter Garden Masonic Lodge. Purchase Tickets (fee required/limited spots)

FRIDAY, OCTOBER 20
Street Performances & Surprises, 6:00 – 9:00 pm
Halloween Light Show on City Hall, 7:00 – 9:00 pm

SATURDAY, OCTOBER 21
Fall-themed Winter Garden Farmers Market, 8:00 am – 1:00 pm
Lego Day at the Central Florida Railroad Museum – A Frightfully Fun Experience, 9:00 am – 4:00 pm
Create a Haunted House Family Event at SOBO Art Gallery, 4:00-5:30 pm, Click here to register (fee required/limited spots available).
Street Performances & Surprises, 6:00 – 9:00 pm
Halloween Light Show on City Hall, 7:00 – 9:00 pm

SUNDAY, OCTOBER 22
Street Performances & Surprises, 6:00 – 9:00 pm
Halloween Light Show on City Hall, 7:00-9:00 pm

FRIDAY, OCTOBER 27
Halloween Spooktacular Preschool Holiday Program, Jessie Brock Community Center, 10:00 am – 12:00 pm
Street Performances & Surprises, 6:00-9:00 pm
Halloween Light Show on City Hall, 7:00-9:00 pm

SATURDAY, OCTOBER 28
Halloween at the Winter Garden Farmers Market
     Market: 8:00 am-1:00 pm / Event Activities: 9:00 am – 12:00 pm
Street Performances & Surprises, 6:00 – 9:00 pm
Halloween Light Show on City Hall, 7:00-9:00 pm

SUNDAY, OCTOBER 29
Street Performances & Surprises, 6:00 – 9:00 pm
Halloween Light Show on City Hall, 7:00-9:00 pm

TUESDAY, OCTOBER 31
Spooky Caboose at the Winter Garden Heritage Museum, 3:00-8:00 pm
Street Performances & Surprises, 6:00 – 9:00 pm
Halloween Light Show on City Hall, 7:00-9:00 pm

Halloween Experience is hosted by the City of Winter Garden to provide a fun way to celebrate the holiday while providing opportunities to support local businesses.

FREE PARKING – ALWAYS!

Convenient parking is always free throughout Downtown Winter Garden, including at the City’s three-level parking garage (160 S. Boyd St.) and the 117-space parking lot (37 N. Boyd St.).