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Enjoy the fall weather while having fun at these local events.


Harvest Sidewalk Sale and Stroll

October 21

Fall themed Winter Garden Farmers Market,

8:00 am – 1:00 pm


Windermere HS Truck or Treat

October 26

Fun, safe Trick or Treating, Food Trucks and Special Performances! All you favorite clubs and sports groups will be handing out treats! Fun for all ages!


Keene's Crossing Elementary Trunk or Treat

October 28

We are excited to announce the second annual KCE Trunk-or-Treat! Sign up to host a car on FRIDAY, October 28th from 6:30-8:00pm in the car loop. Every car must provide their own candy or prizes. We are planning for about 500 kids to joins us. It should be lots of fun with music, costumes and candy.

Each host car must only have ADDitions approved participates listed to sign up. Only those with ADDitions approval will be allowed to hand out candy/treats to trunk or treaters.

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Mangoni's Witches & Wizards Night

October 28

Free bespoke wands will be given to the first 50 witches and wizands to attend. Giveaways I Themed food and Drinks served all night.

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Halloween Pet Costume Contest

October 29

Crooked Can
Your Pets deserve to enjoy Halloween too. Once again Cause 4 Paws Rescue will be back at Crooked Can for Halloween Spooktacular Pet Costume Contest.

We love seeing pets and their owners proudly showing their creativity. Who says Halloween is just for kids? Prizes awarded for the Top 3 costumes. Details will be posted at a later date. See less

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Interactive Movie at the Garden Theatre, Rocky Horror Picture Show (1975, R)

October 30

Preshow, 7:30 pm/Movie 8:00 pm

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Hay Maze at City Hall

Available All Day, Every Day

Fall-Themed Photo Stations
Seasonal Decorations & Light Displays


Craft Affair

November 12

10:00 am – 2:00 pm
Free to attend!
Jessie Brock Community Center, 310 N. Dillard Street

Arts & crafts lovers will enjoy shopping for unique and one-of-a-kind items at the annual City of Winter Garden Parks & Recreation Craft Affair. It is a great opportunity to shop for holiday and gift items! Exclusively our 50+ creative friends make all of the items.

Although our vendors are 50 or older, every one of all ages is invited to shop the fair for unique handcrafted items.

If you are interested in being a craft vendor at this event and you are 50+, complete a Special Event Vendor Policies & Application and submit to the Recreation Administrative Office, 310 N. Dillard Street, via fax 407-656-6504, or via email to Questions, call Parks & Recreation at 407-656-4155.

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Halloween Light Show

Multiple Dates

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

October 21, 22, 23, 28, 29, 30, 31

 7:00 – 9:00 pm
City Hall, 300 W. Plant Street


Whispering Oaks Elemenatary Trunk ot Treat

October 27

6:30 PM – 8:30 PM

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Community Halloween

October 28

12-2 pm Come if you dare to the Halloween Community Event. Food, fun and more!

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Monster Mash with Lift Disability

October 28

Tanner Hall
29 W Garden Ave Winter Garden, FL 34787
Time: 7-9 PM |

Aliens have taken over this year!! Join us for a out of this world Monster of a Night! Have a disability/special need? This is an evening for the whole family to enjoy. There will be dancing, games, food and maybe a few aliens lurking! Come in your best Monster or Alien get up (nothing too scary please) and BOOgie the night away! You won’t want to miss the most epic dance party of 2022!! RSVP TODAY!

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Halloween at Winter Garden Farmer's Market

October 29 

Come out to the market for some Halloween fun at the fall festively decorated Farmers Market. There will be a special Halloween craft to make and take home 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.

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Hope Church Trunk or Treat

October 30

 Special Program during services 9 & 10:30am. Kid-friendly Costumes are welcome for kids 5th grade & below Special Hope Kids programming during both 9am & 10:30am services Family Fun between services at 10am including inflatables, popcorn, cotton candy & more Invite ALL your friends & family. 

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Spooky Caboose at Winter Garden History Center

October 31

3:00 – 8:00 pm

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.

Winter Garden History, Education, and Visitors’ Center, 21 E. Plant Street

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Health & Harvest Festival

November 12

Winter Garden Farmers Market

Free games, fitness activities, giveaways, cooking and gardening fun, and more!

Stay on top of your health with free vision screenings, cholesterol checks, skin cancer screenings, and posture analysis. Bring your bikes and get a free bike safety check from Wheelworks of Winter Garden!

Pick up local produce, get active, and have a blast to stay on top of your health at the same time.


Venom All Stars Nightmare

October 22

$5 ticket

Venom Allstars
1205 crown park circle winter garden

Venom’s Haunted House is back and this time with a twist as we take you on a trip to Camp Venom! This event is a night full of fun for the entire family with all proceeds going to the 23-23 season here at Venom! Open to public so bring all your friends! 

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YMCA Little Monster Mash

October 27

Come in your Halloween best and join us for a Spooktacular good time. There will be a themed Cardio Kids class followed by trick-or-treating. Open to the community for ages 2-5. For question and more information, visit

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Jack-o-latern Glow Trail

October 28

6 pm

Join us for what could be West Orange county's only nighttime Jack-o-lantern hike! The Oakland Nature Preserve's Glow Trail will be lined with Jack-o-lanterns created by members of the community creating an ethereal and beautiful night-time hike. Bring your flashlights and lanterns 'cause it's dark in them their woods. Want to dress in costume? Go right ahead! We will have candy bags for the kids and some cool critters to see. This is a family-friendly event so please dress and act accordingly. Register to donate a pumpkin if you would like. Entry is donation based with proceeds benefitting ONPs education programs.

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Fall Festival

October 29

Found Life Church
1001 W Plant St
Winter Garden, FL 34787

Fun for the whole family including; bounce houses, obstacle courses, carnival games, popcorn, cotton candy, and more! It's all completely free so make plans to be here!


Downtown Winter Garden Trick or Treat Trail

October 29 

This Halloween event has been organized by our group of local, downtown WG shopkeepers!
Stay tuned for more events...

Trick or Treat Trail at participating shops!

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Street Performers and Surprises

Multiple Dates

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

October 21, 22, 23, 28, 29, 30, 31 | Evenings

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Storytime with Susie Jaramillo

November 4

10:30 am
Writer’s Block Book Store

Calling all the parents of our young readers. Storytime with Susie Jaramillo Author of Skeletina and the In-Between World.

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Small Business Saturday Sidewalk Sale

All Day

Small Business Saturday
All Day
Downtown Winter Garden

Kick off the holiday shopping season at the annual Downtown Winter Garden Small Business Saturday Sidewalk Sale. The mom-and-pop shops in historic downtown make this a must stop to observe the national holiday. Stroll and shop the outdoor sale racks in the festive-decorated historic district. Be sure to dash inside for additional promotions and special savings.