Upcoming Festivals Events

Unfiltered: The Christmas Festival

 West Orange High School - OCPS 20 Dec 2025
FESTIVALS

Oranges & Ornaments: A Festival of Trees (Saturday)

 21 E Plant St 22 Nov 2025
FESTIVALS USD 18

Health & Harvest Festival

 Winter Garden Farmers Market 8 Nov 2025
HEALTH-WELLNESS

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Upcoming Live Music Events

Light Up the Lodge!

 700 9th St, Winter Garden, FL 21 Nov 2025
MUSIC

America's Fleetwood Mac Experience

 Horizon High School Performing Arts Center 14 Nov 2025
ENTERTAINMENT USD 35 TO 45

Homegrown in Horizon West Market

 16016 New Independence Pkwy, Winter Garden, FL, United States, Florida 34787 7 Dec 2025
MUSIC

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Upcoming Food & Drinks Events

Flavor Fest: A Taste of Horizon West!

14111 Shoreside Way Winter Garden, FL, United States, Florida 34787 8 Nov 2025
FESTIVALS

Mastering the Art of Table Gala

 Tanner Hall 12 Dec 2025
ART USD 215 TO 589

Dreams Emopwered Foundation @ Popstroke Hamlin

 PopStroke 19 Nov 2025
SPORTS USD 66

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Trending Events in Winter Garden

Johns Lake Annual Boat Parade!

 John's Lake 13 Dec 2025
PARADES

Christmas Golf Cart Parade 2025

 Downtown Winter Garden 6 Dec 2025
CHRISTMAS-PARADES

ChristmasTrivia with Puzzles Entertainment

 Crooked Can Brewing Company 2 Dec 2025
CHRISTMAS

SMALL BUSINESS SATURDAY SIDEWALK SALE & LIVE MUSIC

 Winter Garden Downtown Historic District 29 Nov 2025
MUSIC

Paint & Sip Friendsgiving at UNO Winter Garden

 UNO Pizzeria & Grill 22 Nov 2025
THANKSGIVING USD 48

Venardos Circus - Winter Garden, FL

 16313 New Independence Parkway Winter Garden, FL 34787 20 Nov 2025
WORKSHOPS

Powerful Voices Open Mic Show - Live Music, Comedy, Poetry+ More!

 Winter Garden 30 Oct 2025
ART FREE

2nd Annual effNETS Golf Tournament

 Stoneybrook West Golf Club 21 Nov 2025
SPORTS

Painting at the Preserve with Pepper the Opossum

 Oakland Nature Preserve 15 Nov 2025
ART

America's Fleetwood Mac Experience - Be an usher!

 Horizon High School Performing Arts Center 14 Nov 2025
ART FREE

Winter Garden - Fridays on the Plaza

 Winter Garden 7 Nov 2025
MUSIC

Color Makes Me Happy with instructor Sally Evans

127 S Boyd St, Winter Garden, FL, United States, Florida 34787 8 Nov 2025
ART

Movie In The Park 2025 - Independence Park

 Independence Park 7 Nov 2025
ENTERTAINMENT FREE

Christmas in the Garden

 125 E Plant St, Winter Garden, FL, United States, Florida 34787 5 Dec 2025
MUSIC

Atmospheric Watercolor with Geri Hurbut

 127 S Boyd St, Winter Garden, FL, United States, Florida 34787 7 Nov 2025
ART

More things to do in Winter Garden

Festivals
Live Music
Food & Drinks
Halloween
Comedy
Thanksgiving
Christmas Services
Christmas Carols
Christmas Parades
Parades
New Year
Christmas Markets & Fairs
Pop-Ups