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 PM - 9 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.

October 18-31
Downtown Winter Garden

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

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.

8 AM - 1 PM
Winter Garden Farmers Market

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

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..

12 PM - 5 PM

Home State Brewing
Winter Garden

5 to 9 pm

5 yrs - 12 yrs old

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

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

12 PM - 5 PM​

Suncreek
Clermont

Crooked Can
Winter Garden

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.

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

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

Oakland Presbyterian Church
218 E Oakland Ave, Oakland FL 

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!

All Day
Downtown Winter Garden

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

11 AM - 4 PM
Drifwood Market

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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.

5:00 PM - 7:00 PM

Downtown Winter Garden

​Windermere Brewing
Windermere

3 PM to 6 PM
Sunlight Community Church
607 Avalon Rd
 

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.

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!​

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.

6 PM - 9 PM

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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. ✨

10 AM - 2 PM

6 PM - 9 PM

104 S Lakeview Ave, Winter Garden

4 PM - 8PM​

1411 Shoreside Way

Winter Garden

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6:30 PM - 8:30 PM