New Downtown Association Head Blends Youth, Experience

When Maxx Crowley left Westport for college, he figured he’d never return.

Less than a dozen years later, he’s the new president of the Westport Downtown Association. He replaces Randy Herbertson, who resigned after 6 years to chair the Downtown Plan Implementation Committee.

If Crowley’s name sounds familiar. it is. He’s vice president of SCA Crowley, the longtime commercial, residential and management real estate services firm.

It’s a family business he did not expect to be part of. After Long Lots Elementary, Bedford Middle School and Fairfield Prep, Crowley headed off to Loyola University in Baltimore.

Like many peers, he gravitated to New York for work (advertising, then real estate) and play. But, he realized, he missed Westport. “It’s a special place. I took it for granted,” he admits.

When COVID hit, New York’s real estate market ground to a halt. Westport’s, meanwhile, was on fire.

Joining his father Steve, and siblings Bobby and Judy, at the 40-year-old firm was a “perfect opportunity.” Moving here — and working at SCA’s Kings Highway North office, just off Main Street — made him realize how much he had missed.

Maxx Crowley (right) with (from left) his brother Bob Crowley and father Steve Crowley.

“My mom used to drag us to The Gap, and all the little stores. We’d have lunch at Onion Alley,” Crowley — now 29 years old — says. “Other times I’d ride my bike with my buddies to Starbucks and the library. My first date was at a restaurant downtown. My brother’s first job was at J. Crew. I always loved downtown.”

He knows there were years with “lots of vacancies. It lost some excitement, some of the mom-and-pop feel.”

But, Crowley says, downtown is in the midst of a major rebound. When Herbertson asked him to be part of the DMA — offering “a young perspective, and a fresh set of eyes” — he joined eagerly.

Crowley — who calls downtowns “the heartbeat” of a town — hopes to build on recent DMA initiatives like Westoberfest to make Westport’s a place people head to for fun.

Asked for a SWOT analysis of downtown, Crowley ticked off strengths: “attracting serious merchant talent; cool, fun stores; new restaurants — and being on the river is huge.”

Downtown offers shopping, entertainment, the Library — and solitude. (Photo/Patricia McMahon)

A weakness has been “not doing a good enough job connecting downtown with the rest of the town.” Riverside Avenue, Crowley says, has “incredible stores and restaurants. But it’s easily overlooked.”

One opportunity is “making the river a bigger center point. We can really tap into places like the Library, Levitt Pavilion and Remarkable Theater too.”

As for threats, Crowley cites the impact of online shopping, and the possibility that landlords might raise rents quickly in the future.

Returning to his “hearbeat” theme, the new DMA head wants Westport’s downtown to be a place where people “eat, meet and gather.” Recalling a trip to Italy — where entire towns gathered in a central square to watch World Cup matches on giant TV screens — Crowley envisions similar events here.

It’s what people want when they move here, he says. Though many want more space in Westport than in cities like New York, they miss having “everything you need on your block.” The desire to gather together is strong, he says.

So he’s excited about a variety of ideas. Bill Taibe wants to make Don Memo even more of an outdoor gathering spot. Fleet Feet’s Dave Wright has floated a road race from Compo Beach to downtown.

Dining at Don Memo, last summer. (Photo/Katherine Bruan)

And what about a barge/restaurant on the river? A water taxi connecting Compo, Longshore, Saugatuck and downtown?

Maxx Crowley is open to all that — and more. He says he has a strong board in place, and an excellent staff to implement new projects.

Everything and anything is on the table. The new Downtown Merchants Association  president is ready for action — in a downtown he never thought he’d be part of again.