Maxx Crowley: Downtown’s Revival, And The Rest Of Town Too

As 2020 began, downtown Westport looked bleak. Boarded-up storefronts, empty parking spots, questions about its very future — Main Street and environs were grim.

When COVID struck, downtown looked even bleaker. More stores closed. Fewer people strolled. The cancellation of big events like the Fine Arts Festival seemed like one final cruel blow.

Yet to the surprise of many, life sprouted amid all the real and metaphorical death.

GG & Joe opened in an out-of-the-way Parker Harding corner. Their acai bowls and pastries were instant hits.

Plywood and butcher block paper came down. New stores opened.

Two restaurants — Capuli and Basso — opened to rave reviews. Two bookstores — one new, one used — opened too, within days of each other. Two gelato shops announced their arrival. A highly regarded bakery will soon move in on Church Lane.

Capuli is one of several new restaurants opening downtown.

Counterintuitively, downtown has come back.

And no one is happier than Maxx Crowley.

He’s an unlikely champion for Main Street. He’s young (a 2010 graduate of Fairfield Prep). He worked in New York City, in advertising and real estate. He’s single. You wouldn’t figure him for a suburban guy.

But he comes from a storied family. His father Steve is the “S” in SCA Crowley, a residential and commercial real estate services firm. Since starting work in September with them, Maxx has jumped head first into the downtown renaissance. He’s already a co-vice president of the Westport Downtown Merchants Association.

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

Despite his youth, Maxx remembers “exciting stores,” Onion Alley with its rooftop music, and mom-and-pop shops like Liquor Locker.

He recalls took when chain stores — even big names like Nike and Banana Republic — swooped in. “They took some of the character” of Main Street away, he admits.

COVID was “a weird perfect storm” for Westport, Maxx says.

“There was a lot of loss. People died. Businesses closed. Restaurants struggled.”

But the virus drove people out of New York. Westport welcomed a surge of newcomers. And people who already lived here — but spent 12 hours a day, 5 days a week working elsewhere — suddenly had time to focus on their town.

They walked. They biked. They picked up coffee and lunch, clothes and furniture in places they had never known about.

Landlords struggled. Rents — quite a bit north of $100 a square foot — took a significant hit. But some of those same landlords also realized this was a time for a re-set. They lowered rates, and looked for new tenants. And those were not always the same-old, same-old national brands that could be anywhere.

Some landlords lowered their rents, or accepted late payments. Some offered a few free months, or help with certain expenses.

It was not easy. COVID or not, landlords still have their own fixed costs: taxes, insurance, maintenance and more.

Downtown depends on foot traffic. (Photo/Lynn Untermeyer Miller)

Commercial real estate is “a relationship business,” Maxx says. Relationships often extend far. When one landlord sees another succeeding, they want to be part of the action.

Downtown has many things going for it, Maxx says. One key element is walkability.

“I can park my car. I get my coffee at GG & Joe. I cross the street to Savvy + Grace. My kid” — he doesn’t have one, but you get the point — “goes next door to Brandy Melville.”

That’s not the case in other parts of town. Anyone wanting to cross from Stop & Shop to the cute Peggy’s Cottage Irish store across the street takes his life in his hands.

But the right business in the right spot can succeed anywhere. Maxx points to Terrain: “a beautiful, redeveloped place. No one minds driving there.”

Terrain attracts customers with intriguing displays.

He’s bullish on both Compo Shopping Center too. “Torrey (Brooks, the landlord) is phenomenal,” Maxx says. “He builds relationships with all his tenants.”

There are vacancies there right now. Maxx is hopeful that a “memorable store” comes into the spaces previously occupied by Olympia Sports and Compo Barber Shop.

He also thinks the shopping plaza at the foot of the Sherwood Island Connector — with Restore Cryotherapy, among others — has great visibility.

Further east on the Post Road, Maxx has mixed feelings about Amazon Go, the automated grocery store that’s the rumored replacement for Barnes & Noble.

“People will always want to talk to the butcher and the deli guy. But it’s exciting to see a brand like Amazon come to Westport. There aren’t many Amazon Gos on the East Coast.”

And at the Southport border, Maxx notes that the Home Goods shopping center always has solid occupancy.

The one piece missing from downtown Westport, he says is “experiential” places. He cites the lack of restaurants on Main Street (though a new one will at some point replace Tavern on Main). “In a perfect world,” Maxx adds, “the ice rink would move from Longshore. And music always brings people together. We might not have bars with bands anymore, but they played on Church Lane last summer. That was great. And what about a stage downtown?”

Westport’s Fine Arts Festival is an “experiential” event. It has moved back to Main Street, from Parker Harding Plaza.

He’d also like to see downtown connected, somehow, to Saugatuck. “So many great stores across the river don’t get the attention they deserve,” he says.

“Europe has pedestrian bridges. It’s a beautiful walk along the river. This isn’t Amsterdam. But a bridge or two couldn’t hurt. Can you imagine having dinner at Bartaco, then walking across a bridge — without traffic whizzing by — to have a gelato on Main Street. Then you window shop, and run into friends. That’s a real downtown.”

Meanwhile, Saugatuck itself is filled with “wonderful, local restaurants and markets and shops. Viva and the Duck are anchors. It’s very walkable. There will always be activity there.”

The “ultimate connection” to downtown, he believes, is Longshore and Compo. A restaurant at the beach — and a shuttle between there and downtown — would be “amazing.”

Though not yet 30, Maxx says he has “always” been excited about downtown. Now he sees newcomers getting excited too.

All over town.

24 responses to “Maxx Crowley: Downtown’s Revival, And The Rest Of Town Too

  1. Cathy Walsh

    Max-keep going. So refreshing. Music everywhere please and expand the events.

  2. Ferdinand G. Jahnel

    How about putting cobble stones on Main Street, and make it a pedestrian zone – Europeans have enjoyed walkable downtowns like that for a long time, and it draws people in. I say do it!

    • Elisabeth Keane

      Indeed, European cobblestone streets have been around for centuries. Cobblestones are visually attractive but difficult and imprudent for someone with compromised vision or recovering from an injury or surgery when being sure-footed is key. Folks wearing a leg or foot cast or using crutches, walkers, and wheelchairs would be excluded from Main Street. Perhaps there is a safer way.

      Campbell, CA. (next to San Jose) has a marvelous downtown. The narrow Main Street is lined with shops for several blocks, many places to eat, and the area ambience encourages strolling. Lights strung across the street here and there provide a festive element at night. (Be alert for the occasional Stop sign.) Granted, their climate is more temperate than ours but Campbell’s Main Street is terrific. When I was there last it was still open to two-way traffic.

  3. Fred Cantor

    Maxx: in case you haven’t read about it, Laguna Beach has closed off the bottom one-way portion of its Main Street equivalent, Forest Avenue, and turned it into an outdoor pedestrian mall with temporary structures. Obviously Laguna Beach has more temperate weather and I think Forest Avenue might be less critical than Main Street to local traffic flow, but, in any case, here are some photos of what they have set up:

  4. Matt Bannon

    Great article and hope for future business’s to come to our town
    Your comment on Torrey B is right on target. We at New England Hemp Farm have seen first hand how landlords and tenants can work together, especially during the height of Covid

    The Future is Bright

  5. Maxx

    Your idea of a summertime shuttle between Compo Beach, Longshore and downtown hits the nail squarely on the head. As the Director of the Westport Transit District it’s one of the projects I’ve already thought about implementing. For more information about the Westport Transit District’s current shuttle service, Wheels2U Westport, including fares, service area and hours of operation, see

  6. Nancy Vener

    A restaurant like the old standby SHIPS would draw all ages and families.

    • Caryl Beatus


  7. Robbie Guimond

    Dare I say a summer “water taxi “connecting Saugatuck to downtown? Anyways….. Great job Crowleys !!!

  8. Pamela Long

    How about shutting down main st. to traffic on Saturday nights in the summer? Bring in food trucks, a band, stores could stay open late for shopping.

    • Isabelle Breen

      Love this idea Pam! I miss the roof top bands that used to play at Bobby Q’s.

  9. Irene Mastriacovo

    Love the ideas and enthusiasm. Wheels2U shuttles on weekends with pick ups not only from the beach but also from the Park & Ride lots and train stations; Water Taxi is a fun idea though scheduling around the tide might be tricky, closing Main and Church to traffic is ideal and keeping stores open later will keep these streets lively. I say “Yes” (though my knees say no) to a downtown skating rink – ice in winter and roller skating in spring, summer & fall. And while I’m at it, can we get David’s Tea back?

    • If we can get the Wheels2U shuttle going the thought is it would stop at Longshore and the Senior Center as well as Compo Beach.

  10. Bill Strittmatter

    Meh to ice rink. A roller coaster on the other hand….

  11. What happened to the group who wanted to do a distillary a few years ago? I think there are some Main Street spots open that would work. Cornor of Main and RT 1 now vacated by Pop T’art. or the Kleins building? Love the outdoor ice rink and skating rink idea too. Water taxi is cool but tough but could be done if it’s kept unstructured and could be event driven. Tie it up at library and go to dinner, shopping and catch an outdoor concert.

  12. Rozanne Gates

    Recently I watched the film “Roman Holiday” and toward the end of the movie there was a scene that took place on a floating dance barge on the river in Rome. It was beautifully lit with string lights and there was a bar to order drinks. Why couldn’t Westport do something like that on the Saugatuck River at Parker Harding Plaza? Plenty of parking. A dance floor on the river just like in the movie.

  13. James Waldron

    With the legalization of marijuana n CT looking like it’s going to happen, a piece of legislation strongly supported by our own Senator Will Haskell, and with the proliferation of gelato shops now opening downtown, Maxx I think you know what store is next or Main St to get it, buzzing.

    Best of luck.

  14. Arline Gertzoff

    How about a Dollar Store or General Store with more affordable merchandise.An affordable store or two goes together with affordable housing ./Sat marketplace .

  15. Caryl Beatus


  16. I love Laguna as much as I do Westport and that looks like a great idea Fred!!

  17. Thank you all for the kind comments! These are all great ideas. Please feel free to shoot me an email with any more ideas people have. I will do my best to make a rally around it. We have such a wonderful town and it will only continue to get better with these support efforts. Maybe a mix of the closed streets in Laguna and cobble stones from Europe?!

    LOVE the water taxi idea!!