Bring holiday cheer and create lasting Christmas memories with the family this season at 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 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
32nd Annual Light Up Winter Garden
on Friday, 6 Dec, 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
on Saturday, 7 Dec, 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!!

Sleigh Ride with Santa 2019
on Saturday, 14 Dec, 6:00 PM
at Historic Winter Garden, Florida
104 S Lakeview Ave, Winter Garden, FL 34787
Attending Interested

Don't miss out on a Sleigh Ride with Santa through Downtown Winter Garden during the Holiday Season! From 6pm to 9pm, you will get a chance to celebrate with Santa. Check back in for the link and information on how to register. Coming soon!

Horse Drawn Carriage Tours 2019
on Saturday, 7 Dec, 5:30 PM
at Historic Winter Garden, Florida
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 Merry Winter Garden Light Show
on Saturday, 21 Dec, 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

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

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.

Winter Garden Christmas Spectacular
on Saturday, 21 Dec, 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!

A Christmas Carol: A Ghost Story of Christmas
on Friday, 22 Nov, 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