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.

11 responses to “New Downtown Association Head Blends Youth, Experience

  1. Annette Norton

    As a local business owner downtown, a board member of the Westport Downtown association, I am very excited to welcome Maxx as the new president. Looking forward to making even more memories in our uniquely Westport Downtown.

  2. Congrats Maxx! It’s really great to have homegrown talent stepping up to help the town.

  3. Dredge the river and we could have a dinner barge or water taxi to Longshore. Could be great.

  4. Thumbs up for the water taxi! We had them in Sydney and they’re such an entertaining way to get around.

  5. Kathryn Sirico

    Congrats Maxx…..we need young, smart, forward thinking people moving Westport into the future ….your father did it in the 80’s and forward and you will carry the baton for the next generation!

  6. Eric William Buchroeder SHS ‘70

    A water taxi to Longshore. How bucolic!!! Carbon footprint much?

  7. Elisabeth Keane

    The Black Duck is a barge restaurant.

  8. Bill Strittmatter

    Not a big fan of dogs in stores or restaurants. Well, maybe those tiny ones that fit (and stay) in a purse are OK in stores. Any mistakes they make are probably just the owners problem.

    On a related note, how about real estate open houses? As in someone walking their dog sees an open house and decides to check out their neighbor’s house. With their full sized standard poodle. When approached by realtor, claimed it was a service dog. Seriously.

  9. Donald Bergmann

    I take the opportunity of this story to express my strong support for Randy Herbertson and the work Randy is doing as Chair of the DPIC. Under First Selectwoman Jen Tooker, Westport has just issued an RFP for extensive design services for Parker Harding, Jessup Green and more. The task and its success will confront many hurdles. All interested need to be supportive. First Selectwoman Tooker also needs to generate momentum for the dredging of the Saugatuck.
    Don Bergmann

  10. Congrats and welcome back to the “Port” Maxx!

  11. Celeste Champagne

    Always great to see news of downtown and revitalization.
    Unfortunately I seem to have dropped off the “06880” eMail list as this was one of the last I received. Don’t know how this happened or how to get back on!