The Tasting Room
Join us the first Monday of the month at The Tasting Room. A portion of the proceeds will benefit Matthew's Hope.

5:45PM - 7PM
Showcase of Citrus
15051 Frank Jarrell Rd., Clermont, FL  34714
 

Join us for line dancing and lessons with certified dance instructor, Jazzy Durgin. Dancing takes place under the Big Red Barn for $10 per person. Arrive early to grab a snack or drink beforehand.

9AM - 1PM
Sip, shop and stroll downtown Oakland

9AM - 2PM
Sip, shop and stroll downtown Clermont’s restaurants, shops, breweries, and shops.

7PM - 9PM
City Hall
Downtown Winter Garden

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Halloween Light Shows on City Hall

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Market 8AM - 1PM
Activities 9AM - 12PM
Downtown Pavilion

104 S Lakeview Ave, Winter Garden

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Special Halloween craft to take home at the KidZone tent (at Downtown Parking Garage Plaza). 

2PM - 3:30PM
SOBO Art Gallery

 Winter Garden

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Work together to turn a prepared cereal box on a base into an awesome “Haunted House.” You will be amazed by your finished creation! All materials and step-by-step guidance are provided. This popular family event fills up quickly!

Questions, call 407.347.7996.

$38 per house for 1 adult + 1 child

$6 each additional artist

Garden Theatre

 Winter Garden

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The ambiance of the historic Garden Theatre is the perfect setting to watch classic Halloween movies. 

Purchase your Flix tix for $5.00 (no added fees or tax). Budget-friendly concessions too!

5PM - 7:30PM

Betty J's Florist
 Winter Garden, FL

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Stop by for a ghoulish good time complete with refreshments and a live drawing. Costumes are welcome but not required. Let’s get together for a spooky good time!

5PM - 7PM
Downtown Winter Garden

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"Trick or Treat" for kids to stop in while wearing their costume to grab Halloween candy.

5PM - 8PM
Southern Hill Farms
Clermont, FL

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Come enjoy some great music from Jaclyn Hayden! BBQ, drinks, desserts and more! A silent auction will start two weeks before the event and end that evening.

4PM - 8PM
Uno - Winter Garden

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Decorate (and eat) cookies in fall colors! Plus the best pizza and food around! Great for families and friends. The craft is free to attend and decorate the cookies.

6PM - 9PM
Downtown Winter Garden

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FREE children’s activities, food, music, raffles, meet and greet with your local police officers, crime prevention tips, and more!

10AM - 12PM
Jessie Brock Community Center

310 N Dillard St, Winter Garden

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All preschoolers welcome! FREE fall carnival games while dressed in their spookiest costume. Finish the morning off with holiday-themed crafts and trick or treating! 

The Showcase of Citrus
15051 Frank Jarrell Rd, Clermont

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7th annual Pumpkin Ponderosa at The Showcase of Citrus! Enjoy themed treats and beverages, decorative photos ops, and festive activities for the whole family to enjoy!

7 PM - 9 PM
Come enjoy live music every Friday at the Centennial Plaza Gazebo.

9AM - 1:30PM
Sip, shop and stroll downtown Windermere. 

6:15 PM - 7PM
Horizon Yoga

This is an all-level cool flow yoga class. Our rotating teachers will guide you through a 45-minute yoga flow with a combination of standing and floor-based poses. This is great for beginners and experienced yogis alike.

5PM - 8PM
CFL Railroad Museum

101 S S Boyd St, Winter Garden

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$5 ticketed fundraiser to see up-close the custom-built Lego trail layout with Halloween/Holiday-themed sections. Enjoy treats, a photo booth, coloring table, a Lego block fun table, artifact hunt, music, and more!

12PM - !:30PM
Island Touch Premium Coffee

Ocoee, FL

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You'll leave class with a great understanding of the basics of sugar cookies plus a few cool techniques we'll cover in class!

4PM - 8PM

Hamlin

Capture seasonal photos, savor fall treats, and immerse yourself in the festive atmosphere right in the heart of Horizon West. Your pumpkin purchase supports Eight Waves.

11AM - 2PM

Crooked Can

Winter Garden, FL

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Pets love Halloween too! Judging begins at 1pm.

7PM
Crooked Can Brewing

Winter Garden, FL

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Gather your ghouls, summon your spirits, and get ready for a night of fright, fun, and fierce competition. Costumes encouraged… but your knowledge is your best disguise

5:30PM - 8PM

SOBO Art Gallery​

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Enjoy live music, wine, and festive bites while exploring art that captures the warmth, nostalgia, and beauty of the season. Discover one-of-a-kind pieces perfect for gifting or adding a special touch to your home décor. 

12PM - 1:30PM
Island Touch Cafe
Ocoee, FL

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Decorate 6 cookies during this 1.5 hour cookie decorating class & working with edible gold!
 

If you're looking for cookie favors for Thanksgiving, this is your class! If you're looking for a sweet cookie snack to enjoy, this is your class!

9AM - 1PM
Oakland Nature Preserve

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FREE admission! Animal interactions, children activities, guided hikes, boat tours ($18) and more! Check for registration below.

6PM - 9PM

Home State Brewing
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The spookiest market night of the year is here! 

DJ KD Queen dropping the beats
Local vendors with treats & treasures
Trick-or-treating at every booth
Dog Costume Contest 

6:30PM - 11PM

Gymnastics USA

Winter Garden

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Parents Night Out events are suited specifically to allow you to have some "me time" while the children have a blast at Gymnastics USA! Come in costume ready for Gymnastics, Haunted House, Gross out room, Costume Contest, Pizza, Popsicles and so much more! 

The Showcase of Citrus

15051 Frank Jarrell Rd, Clermont

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Buckle up for the wildest after-dark thrill ride in town. Our Creative Director put the pedal to the metal… with a zombie riding shotgun! We’re dead-set on giving you an unforgettable night.

5 PM - 8 PM

Sip, shop vendors, food trucks, family entertainment.

8AM - 1PM
Sip, shop over 100 vendors and stroll downtown Winter Garden at this award-winning Farmers Market. Enjoy restaurants, brewery, and shops.

3PM - 7PM weekdays

11AM - 7PM weekends

Oakland Presbyterian Church
218 E Oakland Ave, Oakland FL 

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Special activities and bounce houses on Saturdays! Come meet your neighbors and buy a pumpkin.

6:30PM - 9PM
Oakland Nature Preserve

Oakland, FL

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West Orange county's only nighttime Jack-o-Lantern hike at Oakland's Nature Preserve! Candy bags for the kids and some cool critters to see. This is a family friendly event so please dress and act accordingly.

11AM - 2PM
VFW
Winter Garden, FL

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Calling all ghost, goblins and witches too!
Post 4305 Auxiliary is having a Halloween party and we’re inviting you!! There will be spooky treats and hotdogs for your delight. Along with games and witches brew! We will have a little something for parents too!

6PM - 8PM
HCA FL WO Emergency

 Winter Garden

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Bring the family for candy, games, costumes and a visit from fire trucks!

5PM - 7:30PM

Betty J's Florist
 Winter Garden, FL
 

​Bring the kiddos to @jojosshakebar for the Kids' Halloween Bash at Pointe Orlando on Sunday, October 26, from 11 AM to 12:30 PM
For $32, tickets include an entrée,
our Cookies 'N' Scream Shake, pumpkin painting, a mummy wrap contest, and a costume contest

3PM - 8PM
Winter Garden Heritage Museum

1 N Main St, Winter Garden

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Enter if you dare as the beloved Chessie Caboose turns into a fright zone on Halloween. Climb the steps into the dark recesses of the caboose outside the Winter Garden Heritage Museum to see what family-friendly frights await. There will be treats – to go with the tricks. Free to enter, donations appreciated.

7 AM - 3 PM

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Come out to the Challenge 22 tribute walk and actvities in efforts to prevent PTS Suicide of Veterans.

12PM - 1:30PM
Island Touch Cafe
Ocoee, FL

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Decorate 6 cookies during this 1.5 hour cookie decorating class & working with edible gold!
 

If you're looking for cookie favors for Thanksgiving, this is your class! If you're looking for a sweet cookie snack to enjoy, this is your class!

2PM - 7PM
Home State Brewing
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Here’s what’s in store:
Live Polka Band, Carnival Games
Dunk Tank, Pretzel Necklace Station
Stein Holding Competition, OKT Merch
Beer Puppeteers, And more!

Times Vary

Crooked Can Brewery

Winter Garden, FL

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Award-winning craft beer, food specials, and live entertainment on the main stage. From traditional polka bands and roaming performers to the epic stein holding contests and the fan-favorite Wiener Dog Races, there’s something for everyone to enjoy.

5:30PM

WO Junior Service League 

Oakland Park​
 

Run or walk and enjoy the creative decorations. This unique, nighttime, family-friendly 5K is sure to be fun for everyone. Features a 5K, a Kid’s Fun Run, games, treats, festive activities, food trucks, live DJ, and much more.