Seasonal & Holidays
2025 New Milford Holiday Guide: Lights, Festive Fun & Good Cheer
From small-town charm to seasonal celebrations, these hometown holiday highlights bring the spirit of the season to life.
The holiday season has arrived in New Milford, bringing twinkling lights, cheerful events and plenty of ways to make memories close to home. From light displays to beloved local traditions, here are the hometown holiday highlights you won’t want to miss.
Please note: Dates and details are subject to change, so be sure to check with each organizer before you go — many events require tickets or reservations in advance.
Bethlehem Christmas Town Festival
When: Friday, December 5, 2025 from 5:00 PM – 9:30 PM & Saturday, December 6, 2025 from 9:30 AM – 4:00 PM
Where: 22 Main Street South, Bethlehem, CT
This iconic festival features the lighting of an 85‑foot tree, an illuminated fire truck procession, a 5K race and a decorated vehicle contest. Visitors enjoy craft vendors, food booths, and live entertainment throughout the weekend. Just a short drive away from New Milford, this charming festival remains one of the region’s most beloved holiday traditions.
More info: christmastownfestival.com
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Light the Lights – Winter Festival
When: Saturday, December 6, 2025 | 3:00 PM – 7:00 PM
Where: CityCenter Green, 1 Ives Street, Danbury, CT
Downtown Danbury transforms into a winter wonderland with a 40‑foot holiday tree, Santa’s arrival by fire truck, and a festive fire truck parade. Guests can enjoy holiday shopping, live entertainment and free cookies and hot chocolate. This free event is family‑friendly and highly popular.
More info: citycenterdanbury.com/event/2025-light-the-lights-winter-festival
Kent Barns Holiday Market
When: Saturday, December 6, 2025 | 12:00 PM
Where: 6 North Main Street, Kent, CT
This festive market in nearby Kent brings together local artisans, makers and specialty vendors for a day of holiday shopping in a charming barn setting. Guests can browse handcrafted gifts, seasonal décor, and gourmet treats while enjoying the cozy atmosphere of Kent’s historic village. The event also features live music and family‑friendly activities, making it a perfect stop for holiday cheer and unique finds.
More info: facebook.com/events
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Litchfield Holiday Stroll & Parade of Lights
When: Sunday, December 7, 2025 | 3:00 PM – 5:00 PM
Where: Litchfield Green, Litchfield, CT
Bring your family out to the Litchfield Green for live music, cookies, hot cocoa and visits with Santa and Mrs. Claus. Around 4:15 PM, the sparkling Parade of Lights begins, featuring illuminated fire trucks, ambulances, decorated vehicles and bikes. The evening concludes with the official tree lighting on the Green.
More info: beldenhouse.com/culture/holiday-stroll-tree-lighting-and-parade-of-lights-2025
Yule Celebration at The Maxx
When: Saturday, December 20, 2025 | 2:00 PM – 6:00 PM
Where: The Maxx, 94 Railroad St, New Milford, CT
This festive ball here in New Milford includes music, dancing, vendors and activities for the kids. Highlights include a holiday cookie fundraiser and winter clothing drive, making it both celebratory and community‑focused. Formal attire is encouraged for a magical seasonal gathering.
More info: allevents.in/new-milford/yule-celebration/200029165309012
TheatreWorks New Milford – “What the Dickens”
When: Select evenings December 4 – 21, 2025 | 8:00 PM (2:00 PM matinee available December 21)
Where: TheatreWorks, 5 Brookside Avenue, New Milford, CT
This comedic homage to A Christmas Carol follows community theater actors attempting to perform the classic entirely from memory. Hilarious mishaps often ensue, making it a lighthearted seasonal performance.
More info: theatreworks.us/show/what-the-dickens-2025
Northern Lights Limited Train Ride
When: Select evenings November 22 – December 23, 2025 (after December 3) | Times vary; see website for available timeslots
Where: Railroad Museum of New England, 242 East Main Street, Thomaston, CT
In nearby Thomaston, this illuminated evening excursion takes passengers through a winter wonderland en route to the “North Pole.” Riders meet Santa and Mrs. Claus, sing carols with elves and enjoy festive cheer. Most magical of all, each child receives a special gift from Santa’s toy bag.
More info: rmne.org/excursions/northern-lights-limited
Enjoy the season, make a few memories close to home and have a happy holiday, New Milford!
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