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Enjoy the fall weather while having fun at these local events.
Check back as we add more events weekly!

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Make a Difference Monday

First Monday

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.

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Ocoee Market

First Thursdays

5 PM - 9 PM

Sip, shop vendors, food trucks, family entertainment.

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Winter Garden
Farmers Market

Every Saturday

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

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Hay Maze & Seasonal Decorations

Available All Day, Every Day

October 18-31
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

18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31

 7 PM– 9 PM
City Hall, 300 W. Plant Street

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

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Health & Harvest Festival

November 2, 2024

8 AM - 1 PM
Winter Garden Farmers Market


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

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Cookie Class

September 14

12 PM - 1:30 PM
Flour, Eggs and Yeast

at Island Touch Premium Quality Coffee
 

Welcome in Autumn sugar-style! Come join me in Ocoee, FL for an introduction to the basics of cookie decorating..

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Oktoberfest, Ja!

September 28

12 PM - 5 PM

Home State Brewing
Winter Garden

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Parent's Night Out

October 4, 2024

5 to 9 pm

5 yrs - 12 yrs old

Kids will enjoy dinner, fun-filled educational games and activities. While you get time away. 

Roper YMCA
100 Windermere Rd | $25 - $40 per child

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Suntoberfest

October 5 - 6th

12 PM - 5 PM

Suncreek
Clermont

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Oktoberfest

October 18 - 20th

Crooked Can
Winter Garden

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Free Family Bingo

Every Tuesday

6 PM - 8 PM
Gator Dockside Windermere

Family-friendly Bingo brought to you by Bizzy Air.

Bingo hosted by MissingLink Entertainment
BINGO is free to play, with gift card prizes, music, and great company.

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Oakland Farmers Market

2nd & 4th Thursday

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

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Clermont Farmers Market

Every Sunday

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

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Oakland Pumpkin Patch

October 6 - 31st

Oakland Presbyterian Church
218 E Oakland Ave, Oakland FL 

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Stoneybrook West Golf Club

November 1 & 2

Friday 3 PM to 9 PM

Saturday 12 PM to 9 PM
Market 12 PM to 4PM

Open to the Public
 

Food, Live Music, Hay Rides, Vendors and more!

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Small Business Saturday

November 30, 2024

All Day
Downtown Winter Garden

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

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Taste of Fall 

September 14

11 AM - 4 PM
Drifwood Market

Join us for a Flavorful Celebration of Autumn! at our 4th Annual Taste of Fall event on Saturday, September 14th, 2024.

Get into the holiday spirit with us, indulge in food samples, holiday sips and shop fall merchandise and get ready for Fall season.

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Harvest Sip 'N' Shop

September 26

5:00 PM - 7:00 PM

Downtown Winter Garden

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Oktoberfest

October 4 - 6

Windermere Brewing
Windermere

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Sunlight Community Church

October 19th

3 PM to 6 PM
Sunlight Community Church
607 Avalon Rd

 

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Fridays on the Plaza

Every Friday

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

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Windermere Farmers Market

Every Friday

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

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FREE Community Yoga

Every Friday

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.

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Street Performers and Surprises

Multiple Dates

October

18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31

6 PM - 9 PM

A family friendly spooky Halloween Experience throughout downtown Winter Garden. Live entertainment, animated light show, Hay Maze, Photo Spots and more!

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Challenge 22

November 2

7 AM - 3 PM

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

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Children Museum Fundraiser

September 12

6 PM - 9 PM

Night at the Children's Museum invites you to come out and discover a magical night filled with captivating entertainment, a thrilling live auction, and a delicious dinner accompanied by specialty cocktails. Experience the joy and wonder of our new exhibits designed to inspire young minds and spark creativity. ✨

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Nature Fest

September 21

10 AM - 2 PM

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National Night Out

October 1, 2024

6 PM - 9 PM

104 S Lakeview Ave, Winter Garden

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Hamlin Pumpkin Patch

October 5

4 PM - 8PM

1411 Shoreside Way

Winter Garden

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Wine Down Wed Pop Up

October 16th

6:30 PM - 8:30 PM

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