Jolly, Santa, festive food, horse-drawn carriages. On the first Friday of December every year, the Downtown Milford Business Association (DMBA) holds the annual Lamplight Stroll. Starting in the early 2000s, the Lamplight Stroll has become one of the most popular Christmas events in Milford.
The Lamplight Stroll started as a way to encourage the community to come out and shop downtown for the holidays, focusing more on the small businesses.
During the Lamplight Stroll, families will be able to visit Santa and his elves, take festive candid photos for their Christmas cards, and see the local small businesses and vendors on the Milford Green. Families can participate in a scavenger hunt called the Passport Adventure, where they visit shops and vendors to collect stamps. To win a prize, collect 20 or more stamps. Prizes include a big screen TV, iPads, and more.
The Foran High School band has been playing the Lamplight Stroll for the past 20 years through connections with people in the DMBA. Ms. Jessica Turner, the band and orchestra teacher, brings only the brass instruments, but sometimes expands to other band instruments if they are playing inside.
Turner says, “We do it each year because it is something the student Musicians look forward to and a great opportunity to be connected to the Milford Community.”
Kids in the band get to jazz up their instruments for the Stroll. “I enjoy playing the Lamplight Stroll; it makes me really feel the Christmas spirit,” said a member of the band.

The DMBA is a group of 200-plus businesses located in downtown Milford. Their mission is to build a stronger community and better the environment of downtown Milford. Tray Bonosconi has been the president of the DMBA for the past nine years, having been nominated by her fellow members. Bonsoconi also owns a clothing store called Lovet located at the downtown Harborwalk.
Becoming part of the DMBA is a straightforward process; those interested in joining can visit their website, click on “Apply for Membership,” and complete a simple application. Prices can range based on the membership level. Becoming part of the DMBA will help boost business and strengthen relationships with other businesses.
2025 marks 23 years of the Lamplight Stroll. It will be held on December 5 from 5 p.m. to 9 p.m. This year, there will be 80 to 90 vendors and 24 DMBA businesses participating. The Lamplight Stroll embodies a classic New England evening, reminiscent of scenes commonly seen in movies.
“You have the vendors on the green, you have all of the Christmas lights, all sparkly, and people walking around, they’re all bundled up with hot chocolate, I love it every year,” stated Bonosconi.
With festive music in the air and the glow of holiday lights guiding every step, the Lamplight Stroll continues to be the kind of event that makes even the chilliest December night feel warm.
