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 a daily hay maze, seasonal-themed photo locations, spooky and seasonal decorations, as well as seven nights of an outdoor animated Halloween Light Show and live entertainment.

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

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 at Lego Day at the Museum! A kids’ coloring table and sweet treats will be available for the visiting little ghouls. (For those wanting a sneak peek, there is a Frightfully Fun Lego Night ticketed event on Friday, October 25. 5:00 – 8:00 pm, with proceeds benefitting the museum).

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.
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 for a taste of 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)
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.