On summer afternoons in Woburn, Mass., the familiar jingle of the neighborhood ice cream truck once meant a few extra dollars for two local school teachers. But to their young son Dylan Archambault, it meant something more: a glimpse into entrepreneurship.

“My parents were both teachers, and they had an ice cream truck in the summer to supplement their income,” Archambault says. “I would always tag along and kind of grew up around that. And in college, I took over the business and started continuing along those lines.”

That summer side hustle became Dylan & Pete’s Ice Cream and Catering, which today Archambault proudly describes as “New England’s largest ice cream catering company; maybe even in the country.” With a fleet of trucks, a wholesale operation, and partnerships ranging from colleges to corporate offices to the Lowell Folk Festival, Dylan & Pete’s has been a community staple for over 30 years. 

Breaking into new territory

In those early years, Archambault juggled his business while studying physical therapy at UMass Lowell, often daydreaming about ways to reach new customers. With the help of his brother-in-law Pete, his first employee, he began expanding routes into nearby towns — first Winchester, then Lexington.

From there, Archambault pushed into a different kind of market. He started cold-calling companies out of the Yellow Pages offering corporate catering services. Demand grew, and with it, the business’s scope.

“I never thought I’d be an ice cream man,” Archambault says with a laugh. “But it’s a fun business. We’re delivering smiles. Everyone is happy to see the ice cream man.”

Building a business with community at the core

Over the past two decades, Dylan & Pete’s has evolved far beyond the neighborhood ice cream truck. Today, the company is organized around three core components: catering, special events, and mobile marketing. Trucks appear at colleges, corporate campuses, and festivals. Companies rent branded trucks for promotions and giveaways. The wholesale division supplies ice cream to other vendors.

“It’s very rewarding and very busy,” Archambault says. “From May to the end of September it’s jam-packed and nonstop, seven days a week.”

That pace requires more than trucks and freezers. It requires people. Many employees are college students who cycle out by late summer, leaving gaps during peak season. To bridge them, Archambault leans on family, including his wife and their eight children. “Growth is always the challenge. You never know from year to year where you’re going to be,” he says. “But we’ve had a lot of long-term employees we consider family.”

The company has also made community giving a pillar of its mission. Dylan & Pete’s supports organizations like the Jimmy Fund, the Boston Children’s Hospital Walk, Scooper Bowl, and local police departments. “We’re all about community. We give back and donate wherever possible,” Archambault says. “It’s a way for us to show our appreciation for everything the community does for us.”

The right partners make growth possible

As Dylan & Pete’s grew, so did its operational needs. When the company moved its headquarters from Lowell to Chelmsford after 25 years, Archambault needed financing to buy a new building and invest in a walk-in freezer. That support came from Enterprise Bank — now Rockland Trust, following a recent acquisition.

“The bank was there every step of the way to provide financing at a very competitive and fair rate,” Archambault says. “We have lines of credit with the bank. With all of these receivables out there, it’s comfortable knowing we have that tool when we need it.”

What stood out to him wasn’t just the financial products, but the relationship. “With all of these things going on, it’s pretty busy. But having a partnership with a local bank like Rockland, formerly Enterprise, it’s great to be able to walk in and know people by name, to be able to call and say, ‘Hey I need some funding for this,’ and to know that you’ll get the support you need,” Archambault says. “They simplified the process. We didn’t have to go through a ton of paperwork or interviews. They knew us, they knew our history.”

That relationship-first approach is part of Rockland Trust’s heritage. Founded in 1907 as one of the first “mobile banks,” Rockland Trust has long prioritized accessibility and community connection, a philosophy that mirrors Dylan & Pete’s approach to meeting customers where they are.

David Twiss, the Rockland Trust banker who works closely with Dylan & Pete’s, says that personal connection is what makes the partnership so strong. “As Dylan & Pete’s banker, I’ve focused on being a proactive financial partner who understands both their short-term needs and long-term goals,” Twiss says. “We (Rockland Trust) are committed to supporting their business growth. In 2024, we provided financing for their new headquarters. We also provide digital banking tools to streamline their payments, improve cash flow visibility, and reduce administrative burden.”

“It’s not uncommon for my banker to just check in and say, ‘Hey, what’s going on? Is there anything I can help you with?’” Archambault says. “That’s great because we get so busy in the daily operation of the company. It’s nice to know that there’s someone out there thinking of you and ready to step in and help when the time comes.”

Looking ahead

As Dylan & Pete’s continues to grow, Archambault sees opportunities for expansion, whether by adding trucks or possibly opening a brick-and-mortar store. But his philosophy remains rooted in people, community, and partnership.

“It’s great having partnerships with the Bank, but if you don’t have the people to help you grow, then there really is no company,” he says. “You can only do so much as one person.”

From the jingle of a single truck to a multifaceted enterprise, Dylan & Pete’s Ice Cream and Catering has shown how vision, persistence, and the right support can turn a seasonal side hustle into a regional success story. And with Rockland Trust by their side, the business is well-positioned to keep delivering smiles for years to come.