When does the holiday season actually begin in New Milford? This year the answer is a date. The trees on the Village Green light on Saturday, November 28. Two Saturdays later, on December 12, the bandstand hosts the Carol Sing and Water Witch's fire trucks roll out lit up for the Parade of Lights. The 14 days between those two evenings, and the weekend in the middle, make up the season.
Plan around that sequence and it becomes clear which nights to save for the Green and which ones the indoor venues cover.
Weekend One: The Lights Go On
The Greater New Milford Chamber of Commerce lists its Annual Tree Lighting on the Green for Saturday, November 28, starting at 5:30 p.m. and running until 7:30 p.m. The lights on the Green's trees go up through the United Methodist Church's Men's Group, and Santa comes to visit with children.
The date carries more than the lighting. November 28 is the Saturday after Thanksgiving, and last year the town's Economic Development Commission connected Small Business Saturday to the tree lighting, writing in its 2025 holiday roundup that the pairing brought shoppers into downtown stores and restaurants. In 2026 the timing lines up the same way, so a day of shopping downtown runs straight into the lighting at dusk.
The same weekend has an indoor option. The Silo Cooking School is running gingerbread-house decorating workshops on Friday, November 27, Saturday, November 28, and Sunday, November 29, with sessions at 9 a.m., 11:30 a.m. and 2 p.m. If you book the 2 p.m. Saturday session, the gingerbread is done before the lights go on.
Weekend Two: The Middle Moves Indoors
The first weekend of December has nothing scheduled on the Green. The indoor calendar is the busiest it gets all season.
| Date | Event | Where | Time |
|---|---|---|---|
| Thursday, Dec. 3 | Almost, Maine opens | TheatreWorks New Milford | 8 p.m. |
| Friday, Dec. 4 | Family Ornament Painting Party | Greater New Milford Chamber event | 5 to 8 p.m. |
| Friday, Dec. 4 to Sunday, Dec. 6 | Gingerbread-house workshops, second round | The Silo Cooking School | 9 a.m., 11:30 a.m., 2 p.m. |
| Friday, Dec. 4 and Saturday, Dec. 5 | Almost, Maine continues | TheatreWorks New Milford | 8 p.m. |
The Chamber lists the Family Ornament Painting Party for Friday, December 4, from 5 to 8 p.m. The Silo's second round of gingerbread workshops runs that same Friday through Sunday, at the same three session times as Thanksgiving weekend. If you couldn't get a spot over Thanksgiving, the workshops come back a week later.
TheatreWorks New Milford opens Almost, Maine on December 3 and runs it through December 20, with 8 p.m. evening shows and 2 p.m. Sunday matinees on December 13 and 20. The run covers three stretches: December 3 to 5, December 10 to 13, and December 18 to 20. The middle stretch includes the night of the Carol Sing, so if you want both the Green and the play that weekend, the Sunday, December 13 matinee at 2 p.m. keeps Saturday evening free.
Weekend Three: The Bandstand and the Fire Trucks
The New Milford Commission on the Arts has set its Annual Carol Sing for Saturday, December 12, 2026, at 6:30 p.m. on the Green. The tradition dates to 1977, when it began under bandleader Skitch Henderson, and it still centers on the bandstand, with songbooks handed out and luminaries lit. The Commission's own invitation tells people to bring "hats, mittens, and some holiday spirit," and in mid-December after dark that advice is practical.
The parade starts once the singing ends. The Commission says Water Witch's Parade of Lights follows the Carol Sing immediately. Water Witch Hose Company No. 2 organizes the parade, which CT Insider described in 2019 as a procession of decorated fire trucks and other vehicles. The tradition is much younger than the Carol Sing. By 2020, CT Insider was calling it a newer holiday event that had started several years before. In other words, a carol tradition from the late 1970s and a much newer fire company procession now share one evening.
Here is how it ran last year, on Saturday, December 13, 2025, according to the event listing:
- Participants lined up starting at 5 p.m.
- The parade ran from 6:30 to 8 p.m., right after the caroling.
- The route circled the Green, followed Bridge Street between Main Street and Patriots Way, went along Patriots Way and past Young's Field, then came back up Bridge Street.
- The convoy broke up at Grove Street and East Street.
- Spectators were told to leave downtown heading north, toward Route 7 or by way of Elm Street to Route 202 and Grove Street, and not to try exiting Young's Field toward the bridge.
The 2025 entry call also went beyond the fire company. Businesses, organizations and residents were invited to enter decorated cars, trucks or company vehicles, with registration done in advance by email. If your business or group wants a vehicle in the lineup on December 12, Water Witch's own channels are where the 2026 details will come out.
Where to Eat on Either End of the Evening
Two places that opened this fall bracket downtown on Route 7, one to the north and one to the south.
North of downtown, Contempo Kitchen & Bar is serving lunch and dinner at 300 Kent Road, near the historic Boardman Bridge. The Hartford Courant reported in October that owner Robert Basar, who ran a restaurant in Brooklyn in the 1990s and has spent three decades building homes in Connecticut, opened it in a building that housed the Mattiace family's River Bistro until around 2014. According to the Courant, the menu leans mostly Turkish, Lebanese, Italian, Greek and French, and local pianist Hank Mulligan plays from 6 to 9 p.m. on Fridays and Saturdays. That puts live piano on both of the season's big Saturdays, so dinner after the tree lighting on November 28 or after the parade on December 12 has music. Contempo's website is the place to check current hours.
South of downtown, Alltown Fresh opened on September 3, 2026, at 61 Danbury Road, with a made-to-order kitchen, coffee, a market and fuel. Patch covered the ribbon cutting in September, and the store's location page lists it as open 24 hours a day, seven days a week, with separate kitchen hours. The kitchen keeps its own schedule, but hot coffee before a 5 p.m. parade lineup or on the drive home from a December 20 matinee is easy to find.
Building the Season Around Two Saturdays
On November 28, the Green lights up while downtown shops are in their post-Thanksgiving Saturday. From December 3 to 6, the evenings move indoors to ornament painting, gingerbread, and the first three performances of Almost, Maine. On December 12, the Green returns for luminaries at the bandstand and a procession of lit trucks heading down Bridge Street. TheatreWorks then carries the season through December 20.
Last year the EDC's roundup also listed a Sip and Stroll organized by the Bank Street Group with more than two dozen downtown merchants, held on the Friday between the two big Saturdays. That was December 5, 2025, from 6 to 9 p.m. If something similar returns this year, it would land in the same middle weekend that already holds the ornament party and the play's opening.
For anyone hosting family over the holidays, the timing is convenient. Thanksgiving guests who stay through Saturday get the tree lighting. Anyone visiting around the second weekend of December gets the Carol Sing, the parade and a TheatreWorks performance within 24 hours.
New Milford is home base for Lisa and the team at Bowman Properties, so we plan around these dates the same way you do. If you're hosting relatives this season and they start asking what life is like on this side of Route 7, bring them to the Green on December 12, and when they want a closer look at the town after the parade, Work with Lisa.
