Winter Garden Holiday Events

Mastering the Art of Table Gala

Tanner Hall 12 Dec 2025

Christmas Golf Cart Parade 2025

Downtown Winter Garden 6 Dec 2025

Unfiltered: The Christmas Festival

West Orange High School - OCPS 20 Dec 2025

Light Up the Lodge!

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

Atmospheric Watercolor with Geri Hurbut

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

Oranges & Ornaments: A Festival of Trees (Saturday)

21 E Plant St 22 Nov 2025

'Home for the Holidays' exhibit opening

127 S Boyd St, Winter Garden, FL, United States, Florida 34787 6 Nov 2025

Johns Lake Annual Boat Parade!

John's Lake 13 Dec 2025

Kiddie Academy Winter Festival

15806 Shaddock Dr 20 Dec 2025

Holiday Cocktail Party Cooking Class

The Ancient Olive Gourmet of Winter Garden 9 Nov 2025

SMALL BUSINESS SATURDAY SIDEWALK SALE & LIVE MUSIC

Winter Garden Downtown Historic District 29 Nov 2025

🎉 Kids Friendsgiving Party at UNO! 🍂

3167 Daniels Rd, Winter Garden, FL 34787 19 Nov 2025

Oranges and Ornaments

The Winter Garden Heritage Foundation - Healthy West Orange Heritage and Cultural Center 21 Nov 2025

Holiday Snacks & Sweets Cooking Class

The Ancient Olive Gourmet of Winter Garden 23 Nov 2025

🎄✨ Meet & Greet with Mr. & Mrs. Mouse! ✨🎄

3167 Daniels Rd, Winter Garden, FL 34787 3 Dec 2025

🎄❄️ A Special Christmas Breakfast with Anna & Olaf! ❄️🎄

3167 Daniels Rd, Winter Garden, FL 34787 6 Dec 2025

Orange and Ornaments: A Festival of the Trees

The Winter Garden Heritage Foundation - Healthy West Orange Heritage and Cultural Center 21 Nov 2025

🎄💚 The Grinch is Coming to UNO! 💚🎄

3167 Daniels Rd, Winter Garden, FL 34787 10 Dec 2025

Paint & Sip Friendsgiving at UNO Winter Garden

UNO Pizzeria & Grill 22 Nov 2025

HOLIDAY FLIX AT THE GARDEN

160 W Plant St, Winter Garden, FL 34787-3143, United States 7 Dec 2025

ChristmasTrivia with Puzzles Entertainment

Crooked Can Brewing Company 2 Dec 2025

🎅✨ Letters to Santa & Christmas Crafting Night at UNO! ✨🎄

3167 Daniels Rd, Winter Garden, FL 34787 2 Dec 2025

🎄✨ Christmas Ornament Decorating Night at UNO! ✨🎄

3167 Daniels Rd, Winter Garden, FL 34787 9 Dec 2025

Christmas Breakfast with Anna and Olaf

UNO Pizzeria & Grill 6 Dec 2025

Oranges & Ornaments: A Festival of the Trees with Mrs. Claus

The Winter Garden Heritage Foundation - Healthy West Orange Heritage and Cultural Center 22 Nov 2025

🎄💚 BACK BY POPULAR DEMAND… THE GRINCH IS BACK AT UNO! 💚🎄

3167 Daniels Rd, Winter Garden, FL 34787 17 Dec 2025

Christmas at Hamlin - A Festival of Traditions

14111 Shoreside Way, Winter Garden, FL 34787-5611, United States 6 Dec 2025

Ginger Bread House Family Workshop

127 S Boyd St, Winter Garden, FL, United States, Florida 34787 13 Dec 2025

Dream Finders Homes 12Ks and 5Ks of Christmas

Cinepolis Hamlin 20 Dec 2025