Downtown Transforms into a Two-Week Halloween Experience
September 24, 2024
Winter Garden provides the best treat for Halloween — a 14-day celebration in its historic downtown with free, fun, frightening, family-friendly, festivities for the community. Hosted by the City of Winter Garden, Halloween Experience 2024 (October 18 – 31) features seven nights of an outdoor animated Halloween Light Show and live entertainment, as well as a daily hay maze, seasonal-themed photo locations, and much more!
HAY MAZE AT CITY HALL
Enter if you dare! A winding hay maze will delight visitors daily during Halloween Experience. Located outside of City Hall, you will find surprise scares (and great photo ops!) as you make your way through the maze. Do not worry, everyone escapes in one piece – and with lots of fun memories!
Daily | October 18 – 31 | 10:00 am – 9:00 pm
City Hall, 300 W. Plant St. | Free
STREET PERFORMANCES & LIVE ENTERTAINMENT
You never know what is lurking downtown as spooky characters, jugglers, stilt walkers, and more tricks surprise visitors with pop-up street performances. In addition, live music will fill the night air. Catch the creepy fun on weekend evenings and on Halloween night.
October 18, 19, 20, 25, 26, 27, 31 | 6:00 pm – 9:00 pm
Historical Downtown | Free
HALLOWEEN LIGHT SHOW
Look out! City Hall is under siege by ghosts, goblins, witches, and creepy crawlers as they trek across the walls of City Hall. The 15-minute Halloween Light Show is synchronized to scary tunes and runs in a continuous loop from 7:00 to 9:00 pm on Fridays/Saturdays/Sundays and on Halloween night.
October 18, 19, 20, 25, 26, 27, 31 | 7:00 – 9:00 pm
City Hall, 300 W. Plant St. | Free
HALLOWEEN CELEBRATION AT THE WINTER GARDEN FARMERS MARKET
The fall harvest season is in and the Winter Garden Farmers Market is ripe with pumpkins, gourds, as well as festive autumn décor. Every Saturday, you will find pumpkins of all shapes and sizes that are perfect for carving – and a perfect backdrop for fall photos!
On October 26, the market will host a Halloween celebration with free Halloween craft making for kids at the KidZone tent (across from Parking Garage Plaza on Tremaine Street), as well as live music.
Every Saturday | Market Hours, 8:00 am – 1:00 pm
Halloween at the Market | Saturday, October 26 (Kids’ Crafts, 9:00 am – 12:00 pm) | Free
Downtown Pavilion, 104. S. Lakeview Ave.
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 26 | 9:00 am – 4:00 pm
Central Florida Railroad Museum, 101 S. Boyd St.| Free
SPOOKY CABOOSE AT THE 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.
Thursday, October 31 | 3:00 – 8:00 pm
Winter Garden Heritage Museum, 1 N. Main St.| Free to enter / donations appreciated.
HALLOWEEN MOVIES AT THE GARDEN THEATRE
There’s no better way to see a Halloween movie than inside the the historic Garden Theatre, 160 W. Plant St. Catch the lineup of Halloween classics and enjoy the theatre’s ambiance complete with a star-lit ceiling:
Carrie (1976, R) | Tuesday, October 29 | 7:30 pm
Scream (1996, R) | Tuesday, October 29| 10:00 pm
Young Frankenstein (1974, PG) | Wednesday, October 30 | 7:30 pm
The Blair Witch Project (1999, R) | Wednesday, October 30 | 10:00 pm
Get Out (2017, R) | Thursday, October 31 | 7:30 pm
The Rocky Horror Picture Show Experience (1975/ R) | October 31 | Doors open, 10:00 pm / Movie, 10:30 pm. Join our hosts for games, contests, & prizes, and all-around hilarity before the showing of this classic film.
Movies: are $12 and The Rocky Horror Show Experience is $29 — includes ticketing fee. Purchase tickets.
SEASONAL DECORATIONS & PHOTO STATIONS
You are immersed in the Halloween Experience when you enter historic downtown. Halloween and fall decorations and light displays capture the “haunted” spirit of the season. From hanging ghosts, dangling skeletons, and humongous crawling spiders, to hay bales, scarecrows, and pumpkins, the perfect backdrops abound for seasonal photos! See how many of the themed photo stations you can find!
Daily | October 18 – 31
Historic Downtown | Free
SHOP, DINE, & STROLL THROUGH SPOOKY AMBIANCE
As you stroll through the spooky ambiance of Halloween Experience, be sure to pop inside downtown’s unique shops. The boutiques and specialty retail shops have unique finds for a fall wardrobe update, as well as seasonal décor and more to make your fall holidays special.
There are no shortage of Halloween treats for visitors with a vast array of bakeries, chocolate shops, ice cream parlors, and more along the brick-lined streets of downtown. Take a treat to go as you stroll enjoying the decorations and activities.
Be sure to grab a pumpkin spice latte or another seasonal fan favorite beverage at the coffee shops to fully immerse in fall!
Eateries – from casual to fine dining, offer a variety of outdoor culinary options in the crisp autumn weather to enjoy the Halloween Experience.
DAILY ENTERTAINMENT & ACTIVITIES SCHEDULE
All events and activities are FREE.
FRIDAY, OCTOBER 18
Hay Maze at City Hall, 10:00 am – 9:00 pm
Street Performances & Surprises, 6:00 – 9:00 pm
Halloween Light Show on City Hall, 7:00 – 9:00 pm
Fridays on the Plaza Live Music – Southbound Duo (Bluegrass, Folk), Centennial Plaza, 7:00 – 9:00 pm
Spooky- and Fall-Themed Decorated Downtown & Photo Stations
SATURDAY, OCTOBER 19
Fall-themed Winter Garden Farmers Market, 8:00 am – 1:00 pm
Hay Maze at City Hall, 10:00 am – 9:00 pm
Street Performances & Surprises, 6:00 – 9:00 pm
Halloween Light Show on City Hall, 7:00 – 9:00 pm
Spooky- and Fall-Themed Decorated Downtown & Photo Stations
SUNDAY, OCTOBER 20
Hay Maze at City Hall, 10:00 am – 9:00 pm
Street Performances & Surprises, 6:00 – 9:00 pm
Halloween Light Show on City Hall, 7:00 – 9:00 pm
Spooky- and Fall-Themed Decorated Downtown & Photo Stations
MONDAY, OCTOBER 21
Hay Maze at City Hall, 10:00 am – 9:00 pm
Spooky- and Fall-Themed Decorated Downtown & Photo Stations
TUESDAY, OCTOBER 22
Hay Maze at City Hall, 10:00 am – 9:00 pm
Spooky- and Fall-Themed Decorated Downtown & Photo Stations
WEDNESDAY, OCTOBER 23
Hay Maze at City Hall, 10:00 am – 9:00 pm
Spooky- and Fall-Themed Decorated Downtown & Photo Stations
THURSDAY, OCTOBER 24
Hay Maze at City Hall, 10:00 am – 9:00 pm
Spooky- and Fall-Themed Decorated Downtown & Photo Stations
FRIDAY, OCTOBER 25
Hay Maze at City Hall, 10:00 am – 9:00 pm
Street Performances & Surprises, 6:00 – 9:00 pm
Halloween Light Show on City Hall, 7:00 – 9:00 pm
Fridays on the Plaza Live Music – Renegade Fusion (Country), Centennial Plaza, 7:00 – 9:00 pm
Spooky- and Fall-Themed Decorated Downtown & Photo Stations
SATURDAY, OCTOBER 26
Halloween Celebration at the Winter Garden Farmers Market with FREE Kids Halloween Art Activity
Fall-themed Market: 8:00 am – 1:00 pm / Halloween Kids Art Activity: 9:00 am – 12:00 pm
Lego Day at the Central Florida Railroad Museum – A Frightfully Fun Experience, 9:00 am – 4:00 pm
Hay Maze at City Hall, 10:00 am – 9:00 pm
Street Performances & Surprises, 6:00 – 9:00 pm
Halloween Light Show on City Hall, 7:00 – 9:00 pm
Spooky- and Fall-Themed Decorated Downtown & Photo Stations
SUNDAY, OCTOBER 27
Hay Maze at City Hall, 10:00 am – 9:00 pm
Street Performances & Surprises, 6:00 – 9:00 pm
Halloween Light Show on City Hall, 7:00 – 9:00 pm
Spooky- and Fall-Themed Decorated Downtown & Photo Stations
MONDAY, OCTOBER 28
Hay Maze at City Hall, 10:00 am – 9:00 pm
Spooky- and Fall-Themed Decorated Downtown & Photo Stations
TUESDAY, OCTOBER 29
Hay Maze at City Hall, 10:00 am – 9:00 pm
Spooky- and Fall-Themed Decorated Downtown & Photo Stations
WEDNESDAY, OCTOBER 30
Hay Maze at City Hall, 10:00 am – 9:00 pm
Spooky- and Fall-Themed Decorated Downtown & Photo Stations
THURSDAY, OCTOBER 31
Hay Maze at City Hall, 10:00 am – 9:00 pm
Spooky Caboose at the Winter Garden Heritage Museum, 3:00-8:00 pm (Free to Enter, Donations Appreciated)
Trick or Treat hosted by Participating Downtown Businesses, 3:00 – 5:00 pm
Ghosts & Ghouls Spooky Sip ‘n Stroll – Ghouls Just Wanna Have Fun!, hosted by participating Downtown Shops, 5:00 – 8:00 pm
Street Performances & Surprises, 6:00 – 9:00 pm
Halloween Light Show on City Hall, 7:00-9:00 pm
Spooky- and Fall-Themed Decorated Downtown & Photo Stations
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.), 117-space public parking lot located at 37 N. Boyd St., and at City Hall, 300 W. Plant St.
Halloween Experience is hosted by the City of Winter Garden to provide a fun way for the community to celebrate while providing opportunities to support local businesses.