Winter Garden's Home For The Holidays.
Twinkling lights, festive markets, holiday music and meaningful moments across Winter Garden and West Orange County.
MAKE SPIRITED MEMORIES
Your season, beautifully planned.
Explore the activities from the We Are Winter Garden Holiday Guide and find favorites by interest or location.
Featured Holiday Event
Hometown Holidays
Get ready for a season filled with community engagement and festive spirit!
The Winter Garden Heritage Foundation is proud to present Hometown Holidays: A Winter Garden Heritage Foundation Celebration of Peace and Joy, presented by AdventHealth.
Winter Garden holiday events
-17.jpg)
Light Up Winter Garden
Friday, December 4 | 6–9 PM
Winter Garden City Hall, 300 W. Plant St., Winter Garden, FL 34787
Kick off the holiday season as historic downtown comes alive with sparkling lights, live entertainment, festive activities, and community cheer. The official lighting takes place at 6:15 PM.
-141.jpg)
Winter Garden Christmas Parade
Saturday, December 5 | 10 AM
Starts at Dillard St. & Palmetto St., Winter Garden, FL 34787
Celebrate a favorite hometown tradition with festive floats, community groups, holiday music, and a special appearance by Santa! The parade travels north on Dillard Street and west along Plant Street to Park Avenue.
Holiday Night Market
Saturday, December 5 | 4–8 PM
Downtown Pavilion, 104 S. Lakeview Ave., Winter Garden, FL 34787
Shop for unique holiday gifts, seasonal décor, tasty treats, and festive finds at this open-air night market. Enjoy holiday entertainment and a cheerful atmosphere while supporting local vendors.
-44.jpg)
Winter Garden Christmas Golf Cart Parade
Saturday, December 5 | 6 PM
West Plant Street, Historic Downtown Winter Garden, FL 34787
Watch downtown streets fill with creatively decorated golf carts covered in dazzling lights, festive characters, and colorful holiday displays. A fun Winter Garden tradition the whole family can enjoy!
A Merry Winter Garden Light Show
December 4–6, 11–13, 18–20, 26–27 | 6–9
Winter Garden City Hall, 300 W. Plant St., Winter Garden, FL 34787
Watch City Hall transform into a magical holiday display with animated projections synchronized to festive music. This approximately 25-minute show repeats throughout the evening on 11 select nights.
Main Street Holiday Stroll
December 1, 2026 – January 3, 2027
South Main Street, between W. Plant St. and W. Joiner St., Winter Garden, FL 34787
Step into a holiday wonderland filled with decorated Christmas trees, glowing market lights, festive storefronts, and picture-perfect photo spots. Enjoy a leisurely stroll while shopping and dining downtown.
Holiday shopping and seasonal celebrations
Oranges and Ornaments: A Festival of Trees and Wreaths
November 20 | 5:30–8:30 PM
Heller Hall, 21 E. Plant St., Winter Garden, FL 34787
Experience an enchanting display of beautifully decorated holiday trees and wreaths, featuring one-of-a-kind designs from the community. Enjoy seasonal culinary tastings, festive entertainment, and opportunities to purchase unique holiday creations.
Brunch Among the Trees: An Oranges & Ornaments Culinary Experience
November 21 | 11 AM–2 PM
Heller Hall, 21 E. Plant St., Winter Garden, FL 34787
Enjoy a special holiday culinary experience surrounded by beautifully decorated Christmas trees and festive décor. Celebrate the season while exploring the Heritage Foundation's holiday showcase.
Small Business Saturday Celebration
November 28 | All Day; Music 11 AM–7 PM
Historic Downtown, W. Plant Street, Winter Garden, FL 34787
Shop small and celebrate big! Explore downtown boutiques, discover unique gifts, enjoy seasonal specials, and listen to live music while taking in the charm of Winter Garden's festively decorated streets.
Winter Garden Farmers Market — Holiday Shopping
Every Saturday in December | 8 AM–1 PM
Downtown Pavilion, 104 S. Lakeview Ave., Winter Garden, FL 34787
Find festive bouquets, holiday wreaths, seasonal plants, handcrafted gifts, fresh produce, baked goods, and delicious local treats at Winter Garden's beloved farmers market.
Brunch Among the Trees: An Oranges & Ornaments Culinary Experience
November 21 | 11 AM–2 PM
Heller Hall, 21 E. Plant St., Winter Garden, FL 34787
Enjoy a special holiday culinary experience surrounded by beautifully decorated Christmas trees and festive décor. Celebrate the season while exploring the Heritage Foundation's holiday showcase.
Santa visits, live entertainment and family activities
Santa Visits the Winter Garden Farmers Market
December 12 & 19 | 9 AM–12 PM
Downtown Pavilion, 104 S. Lakeview Ave., Winter Garden, FL 34787
Bring your wish lists and holiday smiles! Santa Claus visits the Farmers Market for festive fun and complimentary photo opportunities while families enjoy shopping for seasonal goodies.
-33.jpg)
Live Holiday Music on the Plaza
Enjoy the sounds of the season as live musicians and festive vocal groups perform holiday favorites beneath the twinkling lights of historic downtown.
Featured performers: Roots & Rosin (Dec. 4), Dickens Carolers (Dec. 11), Santa Sisters (Dec. 12), Mistletones (Dec. 18), and Atlantic City Boys (Dec. 19).
Winter Garden Fire Rescue Annual Santa Run
December 7–12 | 5:45–9 PM nightly
Various Winter Garden neighborhoods; route maps pending
Keep an eye out for Santa and his festive sleigh as Winter Garden Fire Rescue travels through neighborhoods spreading holiday cheer, music, and treats. Different areas of the city are visited each evening.
Chanukah Celebration & Menorah Lighting
December 8 | 6–8:30 PM
Downtown Pavilion / Butterfly Sculpture Park, 104 S. Lakeview Ave., Winter Garden, FL 34787
Join Chabad of Winter Garden for a community Chanukah celebration and menorah lighting, bringing neighbors together to celebrate the Festival of Lights.
Holiday shows, theater and movies
A Holiday Spectacular
November 28 | 7 PM
Garden Theatre on Plant, 160 W. Plant St., Winter Garden, FL 34787
Celebrate the magic of the season through music, song, and treasured Winter Garden traditions. Featuring Opera Orlando, the Orlando Choral Society, the Winter Garden Community Choir, and special guest performers.
It's a Wonderful Life: A Live Radio Play
December 9–20 | 2 PM and 7:30 PM performances on select dates
Garden Theatre on Plant, 160 W. Plant St., Winter Garden, FL 34787
Experience the beloved holiday story presented as a live 1940s radio broadcast, complete with heartwarming moments and nostalgic theatrical charm.
