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. 

October 20-31

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

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!

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!

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 

2:30 PM 

Historic Downtown Clermont

2 PM - 5 PM

Lake Louisa State Park

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.

5PM- 8PM

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

6 PM- 9PM

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

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. 

7PM- 9PM

Home State Brewing Co.

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

5:30 PM – 7:30 PM

Whispering Oak Elementary

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

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!

​

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.

6 PM - 9 PM

Oakland Nature Preserve

Family friendly Jack-o-lantern hike!

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!

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! 

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

Beth's Burger Bar
Winter Garden, FL 34787
6PM

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! 

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.

10 AM - 2 PM

Dream Catcher Horse Rescue

Open House

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.

7PM- 9PM

Home State Brewing Co.

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

9:30 AM

Roper YMCA

Join us for a Spooktacular good time.

Free and open to the community.

Downtown Winter Garden

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

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.

5 PM - 7 PM
Downtown Winter Garden Shops

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

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.

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!

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!

6 PM - 8 PM

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

8-1pm
Winter Garden Farmers Market
Event includes children & fitness activities, games, giveaways, cooking and gardening fun, health screenings, and more!  

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

All Day

4 PM - 5:30 PM
Ticket Required

4:30PM

The Lighthouse School
Winter Garden, FL

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

6:30 PM - 8:00 PM

Keene's Crossing Elementary

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!