Middletown Christmas Events & Things to Do 2025
Your complete guide to the best christmas events in Middletown and surrounding areas
Middletown's festive season comes to life with bright Christmas lights and seasonal programming around Main Street and the Connecticut Riverfront. Events like the Winter Lantern Festival at Lyman Orchards and Holiday on Main Street: Magic of Middletown bring illuminated displays, family entertainment, and market vendors to town squares. Visitors will find things to do from winter festivals and holiday activities to seasonal concerts and craft bazaars that pair neighborhood lights with warm local dining and community cheer for a memorable holiday visit.
Find the best Middletown Christmas happenings this year!
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Christmas Markets
41 eventsLargest decorated Christmas Tree in the area
Christmas Lights
12 eventsOver 1000 handmade Chinese lanterns in a whimsical outdoor display.
Christmas Shows
11 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)
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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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Santa Express Train Ride
(Thomaston)
Visit with Santa Claus on a festive train ride.
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Norwich Winterfest Parade
(Norwich)
Holiday kickoff parade with festive floats and music
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Winter Lantern Festival at Lyman Orchards
(Middlefield)
Over 1000 handmade Chinese lanterns in a whimsical outdoor display.
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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
Events Happening Soon (6)
Christmas Parties Near Middletown
Festive dining experiences, holiday parties, and Christmas-themed food and drink events in Middletown.
Midnight Masquerade: A Coastal New Year's Eve Gala
Ring in the New Year in grand style at Saybrook Point Resort &...
View full details →Middletown Christmas Events Map
See every Christmas event, light display, and market on one map.
Also Near Middletown
Christmas Events Road Trips & Weekend Getaways
Worth the drive for more holiday events near Middletown!
Middletown Christmas FAQ
The biggest annual events include Holiday on Main Street and The Magic of Middletown, featuring tree lighting ceremonies, vendor fairs, parades, and family activities throughout the holiday season.
Middletown’s unique traditions include the Dashing Through Downtown Decorated Vehicle Parade and the community-driven Sand Hill Road light display, which also supports local pet shelters through donations.
Sand Hill Road is widely recognized as the top neighborhood for Christmas lights, with other local neighborhoods offering charming displays ideal for walking or driving tours.
Downtown Middletown hosts several markets during the holiday season, including the Holiday Pop-up Vendor Fair and Magic of Middletown events, where local makers and artisans gather to sell their crafts.
Free activities include enjoying neighborhood light displays, attending the tree lighting ceremony, and exploring Holiday on Main Street events, many of which offer free entertainment and family-friendly fun.
Families can enjoy visits with Santa, horse and wagon rides, holiday crafts, and special themed days like North Pole Comes to Middletown during the Magic of Middletown events downtown.