Holiday Traditions Bring New Milford Together This Winter

New Milford enters the holiday season with a full calendar of long-standing events that bring people downtown year after year. Residents and visitors will see familiar traditions return across the Town Green and business district, each offering a clear sense of continuity for a community that values shared experiences. Together, these activities support local engagement, draw foot traffic to small businesses, and reinforce the Town’s identity as a place where history and public life intersect during the winter months.

Tree Lighting Brings the Green to Life

The annual tree lighting, held on the Saturday after Thanksgiving at 5:00 pm, signals the start of the season for many families. Organized by the Greater New Milford Chamber of Commerce, the event continues a tradition that dates back to 1967. Volunteers from the United Methodist Church Men’s Club work with Angevine Farm to cut, place, and prepare 17 trees that line the Green. Their work reflects decades of steady commitment from residents who return each year to help maintain this practice.

The ceremony is held in conjunction with Small Business Saturday (November 29), which draws shoppers to the downtown stores and restaurants. Families gather at the bandstand, meet Santa, and walk the Green after the lights turn on. For many, this marks the beginning of the local holiday season.

Sip and Stroll Supports Local Nonprofits

On December 5 from 6:00 pm - 9:00 pm, the Sip and Stroll will bring participants to downtown shops for an evening of tasting and browsing. Organized by Bank Street Group with more than two dozen participating downtown merchants, the event directs proceeds to Camella’s Cupboard and the New Milford Animal Welfare organization. It also increases evening activity in the business district at a time of year when local spending is essential to many retailers. Tickets are $30.00 and the event is 21+ only.

Caroling on the Green Continues a Nearly 50-Year Tradition

On December 13 at 6:30 pm, the Town will host its annual Carol Sing around New Milford’s bandstand. Started in 1977 under bandleader Skitch Henderson, the event remains a familiar gathering that connects longtime residents with newer community members. Songbooks, luminaries, and a straightforward focus on group singing keep the program accessible. This year, local vocalist Nancy Reid will lead attendees through a collection of holiday songs.

The Caroling on the Green is free and open to the public, and its consistent format helps maintain stability. It continues to draw people who value local traditions that are simple, predictable, and structured around participation.

Parade of Lights Follows Right After

Water Witch Hose Company 2 will hold the annual Parade of Lights. This event brings decorated vehicles through a designated route around the Green and nearby streets, providing a community activity that relies on strong volunteer participation. Clear safety measures guide the procession, and local organizations and residents often enter vehicles. The parade has become a recognizable December fixture for families who gather downtown to watch.