Windsor Christmas Events & Things to Do 2025
Your complete guide to the best christmas events in Windsor and surrounding areas
Windsor kicks off the holiday season near iconic landmarks with festive events, Christmas markets, and winter festivals like South Windsor CT Winterfest and the Tunnel of Lights. Seasonal attractions include the Annual Gingerbread House Festival and community markets full of handcrafted gifts. From family activities to evening lights tours and festive performances, Windsor offers a lively lineup of things to do that celebrate the spirit of the season.
Find the best Windsor Christmas happenings this year!
Start Here
Christmas Markets
38 eventsLargest decorated Christmas Tree in the area
Christmas Lights
12 eventsThree-mile drive-thru with over 750,000 lights
Christmas Shows
12 eventsGuest principal dancers from NYC Ballet and ABT with live orchestra.
Christmas Activities
33 eventsVisit with Santa Claus on a festive train ride.
Editor's Picks (6)
-
Connecticut Ballet's The Nutcracker
(Hartford)
Guest principal dancers from NYC Ballet and ABT with live orchestra.
-
Bright Nights at Forest Park
(Springfield)
Three-mile drive-thru with over 750,000 lights
-
Santa Express Train Ride
(Thomaston)
Visit with Santa Claus on a festive train ride.
-
First Night Northampton 2026
(Northampton)
New England's premier alcohol-free New Year's Eve arts festival.
-
Norwich Winterfest Parade
(Norwich)
Holiday kickoff parade with festive floats and music
-
A Christmas Carol: A Ghost Story of Christmas
(Hartford)
Hartford's beloved holiday tradition, a classic tale of redemption.
Events Happening Soon (2)
Christmas Giving Opportunities Near Windsor
Give back this holiday season with volunteering and charitable opportunities in Windsor.
Operation Santa 2025
Operation Santa is a vital community initiative in West Springfield, dedicated to ensuring...
View full details →Windsor Christmas Events Map
See every Christmas event, light display, and market on one map.
Also Near Windsor
Christmas Events Road Trips & Weekend Getaways
Worth the drive for more holiday events near Windsor!
Windsor Christmas FAQ
Bright Lights Windsor at Jackson Park is the city’s flagship holiday event, featuring light displays, markets, and live entertainment. The W.E. Made It: Holiday Market and visits with Santa are also highlights of the season.
Windsor’s holiday traditions include the Bright Lights Windsor festival, which transforms Jackson Park into a winter wonderland, and the popular W.E. Made It: Holiday Market showcasing local artisans. The city also offers sensory-friendly “Silent Nights” for visitors with sensitivities.
Jackson Park is the centerpiece for holiday lights, but many residential neighborhoods throughout Windsor also decorate with festive displays. Exploring different areas by car or on foot can reveal charming local favorites.
The W.E. Made It: Holiday Market at Jackson Park is the main destination for local makers, with additional craft fairs and artisan markets held in various neighborhoods across Windsor during the season.
Bright Lights Windsor and the W.E. Made It: Holiday Market are both free to attend. Walking through Jackson Park’s light displays and exploring neighborhood decorations are also great no-cost ways to enjoy the season.
Families will enjoy Bright Lights Windsor’s light trails, visits with Santa, holiday train rides, and the Chalet for warming up with snacks. Many markets and neighborhood events also offer kid-friendly activities and entertainment.