Halloween is Scary Good in Winter Garden

October 5, 2022

Halloween is too fun to be celebrated on only one night. That is why the City of Winter Garden turns its downtown into a spooky, fun-filled Halloween Experience for 11 days! Skeletons perched on street signs, mammoth spiders crawling, bats hanging from trees; it is an amusing outdoor haunted house with a family-friendly twist. In addition, with nightfall comes a variety of entertainment for all ages. Visit downtown for the Winter Garden Halloween Experience 2022 from October 21 to October 31. Costumes are welcome any day!

HALLOWEEN LIGHT SHOW

Creatures, bugs, and all things spooky are invading City Hall as a Halloween animated light show synchronized to music is projected for all to squeamishly enjoy. The 15-minute show runs in a continuous loop from 7:00-9:00 pm on Fridays/Saturdays/Sundays plus Halloween night.

October 21, 22, 23, 28, 29, 30, 31 | 7:00 – 9:00 pm
City Hall, 300 W. Plant St.

STREET PERFORMANCES & SURPRISES

Look over your shoulder and peak around corners as jugglers, stilt walkers, characters, and more will be lurking in downtown, The outdoor street performers, as well as live musical performances, will provide entertainment as you stroll, shop, and dine on weekend evenings and on Halloween.

October 21, 22, 23, 28, 29, 30, 31 | 6:00 – 9:00 pm

HARVEST SIDEWALK SALE & STROLL

Stroll and shop the outdoor sidewalk sale surrounded by the Winter Garden Halloween Experience festivities and decorations. Stores will feature outdoor and indoor special sales, promotions, and seasonal merchandise.

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.

The vast selection of eateries, bakeries, and coffee shops and the expansive outdoor dining patios are ideal for a shopping break and enjoying the fall ambiance. Enjoy seasonal menu items at many of the locations; and of course, the fall fan favorite: pumpkin spice latte.

Saturday, October 22 | Daylong
Historic Downtown

TRICK OR TREAT TRAIL AT DOWNTOWN SHOPS

Bring the kids downtown to trick or treat and follow the candy trail of shops! Nineteen retailers are participating.

Saturday, October 29, 3:00 – 5:00 pm

HALLOWEEN MOVIE SERIES AT THE GARDEN THEATRE

There is no better way to watch fun Halloween movies than in the stunning setting of the refurbished historic Garden Theatre (160 W. Plant St.). The movies series has flicks for both youth and adults. Click here to purchase tickets.

Hotel Transylvania (2012, PG)
Saturday, October 29, 3:00 pm

Psycho (1960, R)
Saturday, October 29, 7:30 pm

Hocus Pocus (1993, PG)
Sunday, October 30, 2:00 pm

WINTER GARDEN FARMERS MARKET HALLOWEEN CELEBRATION

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 fun fall photos!

On October 29, the market will host a Halloween celebration with free Halloween craft-making for kids at the KidZone tent (located next to the Parking Garage on Tremaine Street) as well as live music and family-friendly games on the lawn.

Every Saturday | 8:00 am – 1:00 pm
Saturday, October 29 | Halloween at the Market
Downtown Pavilion, 104. S. Lakeview Ave.

SPOOKY CABOOSE AT THE HISTORY CENTER

Enter the Spooky Caboose – if you dare — stationed outside the Winter Garden History Center. The spooky-decorated caboose has fun frights for all ages. Free to enter/donations appreciated.

Monday, October 31 | 3:00 – 8:00 pm
Winter Garden History, Education, and Visitors’ Center, 21 E. Plant St.

HAPPENING ALL-DAY, EVERY DAY

During the Halloween Experience extravaganza, visitors will find the following all day, every day:

• Hay Maze at City Hall
• Themed Photo Stations
• Seasonal Decorations & Light Displays
• Expanded Outdoor Patios to dine amidst the festive decor while enjoying the crisp weather
• Unique Stores & Restaurants to Shop, Dine & Stroll surrounded by historic charm and holiday ambiance

DAILY HALLOWEEN EXPERIENCE EVENT SCHEDULE

All events and activities are FREE, unless noted otherwise.

FRIDAY, OCTOBER 21

Halloween Light Show on City Hall, 7:00-9:00 pm
Street Performances & Surprises, Evening

SATURDAY, OCTOBER 22

Harvest Sidewalk Sale & Stroll in Historic Downtown, Daylong
Winter Garden Farmers Market, 8:00 am – 1:00 pm
Halloween Light Show on City Hall, 7:00-9:00 pm
Street Performances & Surprises, Evening

SUNDAY, OCTOBER 23

Halloween Light Show on City Hall, 7:00-9:00 pm
Street Performances & Surprises, Evening

FRIDAY, OCTOBER 28

Halloween Light Show on City Hall, 7:00-9:00 pm
Street Performances & Surprises, Evening

SATURDAY, OCTOBER 29

Halloween at the Market – holiday kids craft and special programming at the fall-themed Winter Garden Farmers Market, 8:00 am-1:00 pm
Hotel Transylvania (2012, PG), 3:00 pm, at the Garden Theatre
Halloween Light Show on City Hall, 7:00-9:00 pm
Street Performances & Surprises, Evening
Psycho (1960, R), 7:30 pm, at the Garden Theatre

SUNDAY, OCTOBER 30

Halloween Light Show on City Hall, 7:00-9:00 pm
Street Performances & Surprises, Evening
Hocus Pocus (1993, PG), 2:00 pm, at the Garden Theatre

MONDAY, OCTOBER 31

Spooky Caboose at the History Center, 3:00-8:00 pm
Halloween Light Show on City Hall, 7:00-9:00 pm
Street Performances & Surprises, Evening

FREE PARKING – ALWAYS!

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