Bring holiday cheer and create lasting Christmas memories with the family this season with these Christmas events in Winter Garden. The entertainment will delight audiences of all ages, and includes appearances by Santa, carriage rides through beautifully decorated downtown, an annual parade, spectacular light shows, and a theatrical performance of a classic ghost story of Christmas. 

Stay connected to all the nightlife, events, and more events and things to do in Winter Garden by subscribing to 407area. Check out our Christmas Orlando 2019 Guide for more things to do this holiday season. 

RELATED CONTENT:  Best Restaurants in Winter Garden

Feature Image Courtesy of West Orange Observer
Holiday Boutique Crawl

Holiday Boutique Crawl

on Thursday, 5 Dec, 2019 5:00 PM
at Winter Garden Downtown Historic District
Participants: City of Winter Garden, Driftwood Market
Main Street Downtown, Winter Garden, FL 34787
Attending Interested

Join us in the festive winter wonderland of downtown Winter Garden for our first ever Holiday Boutique Crawl! Enjoy sips & snacks at 9 local boutiques along with some great deals & steals, all evening.

32nd Annual Light Up Winter Garden

32nd Annual Light Up Winter Garden

on Friday, 6 Dec, 2019 6:00 PM
at Historic Winter Garden, Florida
104 S Lakeview Ave, Winter Garden, FL 34787
Attending Interested

It's that magical time of year again! Join us as we welcome the season with live entertainment, vendors, shopping, children's activities and more. Light Up Winter Garden is from 6 to 9 PM; Ceremony starts at 6 PM. *Street lighting at 6:15 PM.

Winter Garden Christmas Parade 2019

Winter Garden Christmas Parade 2019

on Saturday, 7 Dec, 2019 1:00 PM
at Historic Winter Garden, Florida
104 S Lakeview Ave, Winter Garden, FL 34787
Attending Interested

Come celebrate with us in Downtown Winter Garden as the streets fill with amazingly creative decorated Christmas Floats!!

Event Attending
A Merry Winter Garden Light Show

A Merry Winter Garden Light Show

on Saturday, 21 Dec, 2019 6:00 PM
at City of Winter Garden
300 West Plant Street, Winter Garden, FL 34787
Attending Interested

Watch as City Hall is transformed with A Very Merry Light Show from 6pm to 9pm! Using digital mapping and projection, City Hall magically will feature animated holiday greetings! Watch the magic of amazing light shows all around Central Florida, right h

Event Attending
Merry Monday at Winter Garden Village

Merry Monday at Winter Garden Village

on Monday, 16 Dec, 2019 7:00 PM
at Winter Garden Village at Fowler Groves
3251 Daniels Rd, Winter Garden, FL 34787
Attending Interested

Take photos with Santa at Winter Garden Village on December 16 from 5-8PM. Plus, don’t miss Santa’s live reindeer in the clock tower from 6:30-8PM! Please bring a new toy donation for Ronald McDonald House.

Event Attending
Winter Garden Christmas Spectacular

Winter Garden Christmas Spectacular

on Saturday, 21 Dec, 2019 7:00 PM
at Gymnastics USA
13175 W Colonial Dr, Winter Garden, FL 34787
Attending Interested

SNOW IN WINTER GARDEN! EATS & DRINKS, OPEN GYM, WINTER GARDEN VENDORS, LIVE MUSIC, ZIPLINE, BUNGEE, HOLIDAY BAKE OFF, FACE PAINTING, RAFFLES & PRIZES, AND SNOWFALL!

Event Attending
A Christmas Carol: A Ghost Story of Christmas

A Christmas Carol: A Ghost Story of Christmas

on Friday, 22 Nov, 2019 7:30 PM
at Garden Theatre
160 West Plant Street, Winter Garden, FL 34787
Attending Interested

This spirited version of A Christmas Carol puts the ghostly qualities of Charles Dickens’ classic tale center stage. A swirling chorus of ghosts weave through this uplifting holiday story of redemption, magic, and hope as the greedy Scrooge learns the err

Event Attending
Event Attending
Event Attending
Holiday Carriage Tours

Holiday Carriage Tours

on Saturday, 7 Dec, 2019 5:30 PM
at Winter Garden Pavilion
Participants: City of Winter Garden
104 S Lakeview Ave, Winter Garden, FL 34787
Attending Interested

Take a horse-drawn carriage ride through festive downtown Winter Garden from 5:30 pm to 9:30 pm on Fridays and Saturdays!

Event Attending
A Very Merry Farmers Market 2019

A Very Merry Farmers Market 2019

on Saturday, 21 Dec, 2019 9:00 AM
at Winter Garden Farmers Market
300 W Plant St, Winter Garden, FL 34787
Attending Interested

Join us Saturdays for A Very Merry Farmers Market! The Market has quickly grown into a community staple and offers a large selection of vendors from locally grown produce and baked goods, to homemade soaps and fresh flowers, and even live entertainment ea

Holiday Golf Cart Parade

Holiday Golf Cart Parade

on Saturday, 14 Dec, 2019 7:00 PM
at Old Town
5770 West US Highway 192, Kissimmee, Fl 34746
Attending Interested

Join us right before our weekly Car Cruise as residents from Sherwood Forest RV Resort present their personal golf carts in all of their Holiday glory! Golf carts will begin arriving at 6:30pm and will parade down Old Town’s mainstreet before our Car Cru

Event Attending
Traditional Dickens Carolers Performing Holiday Favorites!

Traditional Dickens Carolers Performing Holiday Favorites!

on Saturday, 21 Dec, 2019 6:30 PM
at Centennial Plaza Gazebo
Participants: City of Winter Garden
101 West Plant Street, Winter Garden, FL 34787
Attending Interested

Enjoy this Quartet of traditional Dickens-era carolers performing a repertoire of holiday favorites. Centennial Plaza Gazebo 101 W. Plant St. Free!