Cheshire Christmas Events & Things to Do 2025
Your complete guide to the best christmas events in Cheshire and surrounding areas
Cheshire unveils Christmas 2025 with holiday lights, Christmas markets, and family-friendly winter festivals centered on the town center and cultural sites. Seasonal offerings include lights tours, festive shopping, and community gatherings that bring neighbors together. With a calendar of holiday activities and events like local retreats and performances, Cheshire provides plenty of things to do that make the season cozy and bright.
Find the best Cheshire Christmas happenings this year!
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Christmas Markets
40 eventsLargest decorated Christmas Tree in the area
Christmas Lights
14 eventsOfficial lighting of a 40-foot holiday tree and Santa's fire truck arrival.
Christmas Shows
12 eventsGuest principal dancers from NYC Ballet and ABT with live orchestra.
Christmas Activities
32 eventsVisit with Santa Claus on a festive train ride.
Editor's Picks (6)
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Connecticut Ballet's The Nutcracker
(Hartford)
Guest principal dancers from NYC Ballet and ABT with live orchestra.
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Light the Lights – Winter Festival
(Danbury)
Official lighting of a 40-foot holiday tree and Santa's fire truck arrival.
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Santa Express Train Ride
(Thomaston)
Visit with Santa Claus on a festive train ride.
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A Christmas Carol: A Ghost Story of Christmas
(Hartford)
Hartford's beloved holiday tradition, a classic tale of redemption.
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Glow Hartford Holiday Light Festival & Market
(Hartford)
Interactive light gardens and Santa's Sleigh Adventure
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Miracle on 34th Street - The Musical
(New Haven)
Classic holiday film brought to life as a musical.
Events Happening Soon (2)
Latest News & Updates
Stay informed about holiday events and activities in Cheshire
- Holiday Photo Exchange Event Published: Sun, Dec 7, 2025
- Annual Christmas Bird Count in Connecticut Published: Fri, Dec 5, 2025
Cheshire Christmas Events Map
See every Christmas event, light display, and market on one map.
Also Near Cheshire
Christmas Events Road Trips & Weekend Getaways
Worth the drive for more holiday events near Cheshire!
Cheshire Christmas FAQ
The Lights of Hope luminary event is one of Cheshire’s biggest annual Christmas events, bringing the community together to raise funds for local charities. Additionally, various neighborhood light displays and holiday markets contribute to the festive season.
Cheshire’s Lights of Hope event is a unique tradition where neighbors light luminaries to support local causes. This community-driven event highlights the town’s spirit of giving and togetherness during the holiday season.
Several residential neighborhoods in Cheshire are known for their festive holiday lights and decorations, often featuring coordinated displays and community participation. These areas offer charming walking trails and drive-by viewing opportunities.
Christmas markets and local artisan fairs are typically held in community centers, town halls, and public squares near Cheshire. These venues showcase local makers offering crafts, gifts, and seasonal food and drink.
Enjoying neighborhood light displays, attending free community markets, and participating in local holiday events like the Lights of Hope luminary walk are budget-friendly ways to celebrate the season in Cheshire.
Families can enjoy interactive light trails, festive markets with kid-friendly activities, and special events like visits with Santa or holiday crafts. The Lights of Hope event also offers a warm, family-oriented atmosphere during the holidays.