By mid-afternoon Friday, Oct. 31, Massachusetts Avenue was alive with excitement and festivity as families filled Lexington Center for the 23rd Annual “Trick or Treat with the Businesses.” Organized by the Lexington Retailers Association (LRA), the event turned downtown into a flurry of costumes, candy and spirit — a tradition that has become a cornerstone of the town’s autumn gatherings.
Among the crowd of families were Amy and Mike Brown, longtime Lexington residents who have previously attended the event with their son, Xander. Like many residents, the annual Halloween event has become a family tradition for them.
“It’s a great event for families to gather as a community. The kids get to show off their costumes [,and] meet new friends, and everyone just has a nice time,” Amy said. She added that the afternoon schedule is ideal: “You can enjoy downtown and still head home for neighborhood trick-or-treating later.” The Browns said they look forward to the event each year not only for the fun, but for the sense of connection it fosters. “It’s a wonderful way to see neighbors, discover local shops, and hopefully people will come back and support these businesses.”
Founded in 2000 by Eric and Jerry Michelson of Michelson’s Shoes, the LRA emerged from the Lexington Chamber of Commerce’s retail division. When the Chamber stopped running its retail events, the Michelsons created the association to preserve and expand those traditions. Discovery Day came first; a year later in 2002, the Halloween walk was added.
“It first started as an event that was really designed to bring foot traffic to all retail districts in town,” Eric Michelson said. Since then, it has evolved into a gathering that celebrates both local businesses and the people who support them. And two decades later, that mission endures. “Discovery Day and the Taste of Lexington are more like shopping events,” Jerry Michelson noted. “But this event is to give back to the community.”
Around 70 local businesses participated this year, with 15 organizations stationed in Emery Park, including Keys for Kids, Lexington Education Foundation, and Lexington History Museums.
The event also underscores the LRA’s commitment to keeping community traditions accessible. Participation is now free for merchants, a change made after the pandemic. “We realized that businesses were really struggling,” Michelson said. “We didn’t want to add another cost on top of candy and decorations. Most stores are quiet on Halloween afternoon anyway, so we wanted to make it as easy as possible with businesses to participate. And people are happier doing it.”
At the New Legacy Cultural Center’s table, volunteers quickly ran out of candy as families stopped to chat and take photos. The educational and cultural nonprofit offers Mandarin language and culture classes and hosts a range of cultural workshops and events throughout the year. Executive Director Ting Fang said it was the organization’s first year running a booth after previously joining the event as attendees.
“In the past, we were just part of the crowd with the kids,” said Fang. “This year, we saw an opportunity to set up a table; we’ve seen friends old and new, met many parents who got to know us through the event, and reconnected with our existing students, all excited to see us here. It’s definitely one of the best things about this event.”
Outside of The Lexington Venue, staff members handed out candy beneath the glow of the marquee. Jim, an employee at the venue, reflected on how the event unites Lexington’s business community. He said it’s important for residents to see local businesses “not simply as doorways into something to buy or watch, but as neighbors — from the barbers to the ice cream shop, to the theater and pharmacy — all participating together.” Events like this, he added, “strengthen the idea that merchants in Lexington Center are part of the community, people invested in serving it as much as running a business.”
That sense of shared purpose was echoed by Michelson, who emphasized how vital community participation is for keeping local businesses alive. “You don’t get this kind of support from online websites,” he said. “When you shop local, you’re supporting your neighbors. People value the town center as the living room of Lexington. Well, come down and take advantage of it.”
The Michelsons also noted that the Retailers Association includes more than just downtown shops, representing pockets of small businesses across East Lexington, Marrett Road and Bedford Street. “Every area has people doing great work,” he said. “We just want residents to realize how valuable that is and what keeps it alive.”
And behind the scenes, the event also runs on collective effort. The Lexington Youth Commission delivers balloons each year, with help from William Raveis Real Estate, as well as aid from crossing guards.
As the afternoon wound down, the sidewalks were still buzzing. Parents lingered and chatted with one another, and children compared overflowing candy bags, as volunteers packed up tables. The town’s main street had turned into something more than a shopping center; it became a reflection of the enduring spirit that continues to define Lexington.
I love the Michelsons’ costumes!