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


The William's Holiday House

Multiple Dates

1Mon - Thur 11AM - 10PM

Friday - Sat 11AM - 11PM

Sunday 11AM - 9:30PM
Oakland, FL 

Free to explore outside the William's home filled with Holiday displays. 


The Oakland Pumpkin Patch

Multiple Dates

October 20-31

 11:00 AM – 7:00 PM
Oakland Presbyterian Church
218 E Oakland Ave, Oakland FL 


Spooky Yoga 

Multiple Dates

6 PM- 9PM

October 25 6 PM, 31 9:30 AM, 31 12 PM

Warrior One Yoga-Windermere

Get ready for a spooktacular lineup of Halloween-theme classes with Edsson!


Halloween Howl Night

October 27

6 PM - 9PM
Jim Beech Recreation Center

Ocoee, FL

A free, family-friendly event with a ton of FUN!

NEW this year inflatable corn maze, Trunk or treat, glow hunt, scare zone, pumpkin derby, axe throwing truck. Costume, pumpkin carving & donut eating contests!

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Spooky Social

October 28

9 AM - 4 PM

Social Blends

Ocoee, FL

Social Blends customer appreciation day!
FREE Xtreme hip-hop step class @10am
FREE trunk or treat starts @11am
FREE Spooky slime DIY station *while supplies last
Spooky specials
Discounted merchandise
Raffle entries all day 


Harvest Festival

October 28

2:30 PM 

Historic Downtown Clermont


Trunk or Treat

October 29

2 PM - 5 PM

Lake Louisa State Park

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Spooky Caboose at Winter Garden History Center

October 31

3 - 8 PM

Winter Garden Heritage Museum

Enter the Spooky Caboose – if you dare. The spooky-decorated caboose has fun frights for all. Free to enter. Donations appreciated.

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Jungle 'n' Mingle

November 9

5PM- 8PM

Kick off the holiday season with some late night shopping fun at participating downtown Winter Garden shops!


Comic Controllers
Stick-Er Treat

October 21

6 PM- 9PM

Sticker hunting at all of your favorite local downtown Clermont businesses! $15 in advance.



Multiple Dates

October 20, 21, 22 
Crooked Can

Three days filled with your favorite beers, live music, contests, wiener dog races, face painting, stilt walkers and more. 


Tim Burton Trivia

October 25

7PM- 9PM

Home State Brewing Co.

How much do you know about this darkly-twisted director? 1st, 2nd and 3rd place teams!


Trunk or Treat

October 26

5:30 PM – 7:30 PM

Whispering Oak Elementary

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Fall Festival

Multiple Dates

11 AM - 7 PM
Every Thursday until Nov 12
Southern Hill Farms
Ticket Required

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Street Performers and Surprises

Multiple Dates

6 PM - 9 PM

October 21, 22, 23, 28, 29, 30, 31 

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 27

5 PM - 7 PM

Hope Church + YMCA
Roper YMCA Winter Garden

Join us for a frightfully fun evening for the whole family. In partnership with Hope Church, the event includes decorated vehicle trunks handing out candy and other giveaways, as well as food trucks and outside activities. Free and open to the public.

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Jack-o-latern Glow Trail

October 27 & 28

6 PM - 9 PM

Oakland Nature Preserve

Family friendly Jack-o-lantern hike!

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Fall Festival

October 28

10 AM - 12 PM

Young Innovators Academy

Winter Garden, FL

Games | Petting Zoo | Music
A free, family-friendly event with a ton of FUN and open to the public!


Princess & Prince Halloween Pizza Party

October 28

6 PM - 2 AM

Playa Pizza

Halloween Costume Party and Contest! The theme is Princesses and Princes. At 6 PM we'll invite the kiddos for their own round of prizes and at night we'll have the adult's competition! Enjoy creative cocktails, halloween pastas, and all around fun! 


Witchy Water Paddles & Brunch

October 29

10 AM - 5 PM

Waterfront Park -Clermont, FL
100 3rd Street

We will paddle towards the Tiki Bar. Farmers market on Montrose is open until 2:00. 
SUP Girls Central Florida


Eat, Drink & Be Scary!

October 31

Beth's Burger Bar
Winter Garden, FL 34787

Join us if you dare...for a Halloween scare!! 

 Make sure you wear your best costume  There will be a costume contest, live music by Jeremy Hagen, games, prizes, and more! 


Craft Affair

November 11

10 AM – 2 PM
Free to attend!
Jessie Brock Community Center

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.


Trick or Trot

October 21

10 AM - 2 PM

Dream Catcher Horse Rescue

Open House


Truck or Treat

October 25

5PM- 7:30PM

Windermere HS PTSO

Trunk or Treat, food trucks, performances, games, and more fun for all ages.

Media Center

The Fright Fest Club presents a haunted house experience featuring 5 interactive scare zones.


Trick or Treat Trail
in the Biergarten

October 26

7PM- 9PM

Home State Brewing Co.

Grab the kiddos for this spooky trick or treat trail. Vendors, games, kid & dog costume contest, treats!


YMCA Little Monster Mash

October 26

9:30 AM

Roper YMCA

Join us for a Spooktacular good time.

Free and open to the community.

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Hay Maze & Seasonal Decorations

Available All Day, Every Day

Downtown Winter Garden

Hay Maze, Fall-Themed Photo Stations, Outdoor Patios, Shopping Experiences,
Seasonal Decorations & Light Displays

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Halloween Light Show

Multiple Dates

October 20, 21, 22, 27, 28, 29, 31

 6:00 – 9:00 pm
City Hall, 300 W. Plant Street

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


Trick or Treat Trail

October 27

5 PM - 7 PM
Downtown Winter Garden Shops

Enjoy a spooktacular family night full of costumes, candy, shopping and fun!

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Killer Carnival

October 27 & 28

8PM, 9PM, and 10PM

Winter Garden, FL

Ticketed Event

An Adult 45 min experience with fantastical Sideshow oddity exhibits, a 15 min stage illusion show with magic, mentalism, and death-defying escapes from spiky things, then a final escape through the "backstage maze" with frights lurking around each turn.


Beyond the Grave Rave

October 28

7PM - 11 PM

Home State Brewing 21+

ticketed event

Calling all enthusiasts of The Craft-beer or course! Enter if you dare the spooky lounge & dance party!

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Halloween at Winter Garden Farmer's Market

October 28

8 AM - 1 PM

104 S Lakeview Ave Winter Garden
Come out to the market for some Halloween fun! Children can make a special Halloween crafts and play games. Pumpkin, pumpkins, and more pumpkins -- of all shapes and sizes – can be found. 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!


Monster Mash w/Lift Disability

October 29

6 PM - 8 PM

Jessie Brock Community Center
Come in your best Monster get up (nothing too scary please) and BOOgie the night away!


Health & Harvest Festival

November 4

Winter Garden Farmers Market
Event includes children & fitness activities, games, giveaways, cooking and gardening fun, health screenings, and more!  


Small Business Saturday

November 25

Kick off your holiday shopping at festive-decorated Historic Downtown Winter Garden for a Small Business Saturday celebration with LIVE MUSIC!

All Day


Create a Haunted House

October 21

4 PM - 5:30 PM
Ticket Required


Truck or Treat

October 25


The Lighthouse School
Winter Garden, FL

Fun, Food and Friends!
Trunk or Treat & Pumpkin Contests!


Trunk or Treat

October 26

6:30 PM - 8:00 PM

Keene's Crossing Elementary


Nightmare Before Christmas/Coraline Trivia!

October 26

7:45 PM

Playa Pizza

Enjoy family-friendly trivia each week at Playa Pizza! Arrive by 7:45 to get your answer sheet. Its an event for individuals, families, and teams!

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