Since the day I was born, I have been fortunate enough to call Westport home! I am technically a second-generation Westporter, as my father Steve Crowley was born and raised here as well. My parents moved into the house we still own on Roseville a year before I was born, and the rest was history. Growing up Westport was the ultimate playground, with summers at Compo Beach, going to school at Long Lots and Bedford, and winters sledding down the hills of Staples.
I have always had a love for this incredible town. My first job, at 14 years old, was working for John Cooper at Longshore Golf Course; the “Caddyshack days at Longshore” as I like to call it! I got to know all the people in town, meet some of our celebrity neighbors, and work at one of the gems of our town. On the weekends, riding bikes from the far ends of Post Road East to Downtown with friends nothing was better. Downtown Westport was of course the cool place to hang out and yes, all the money I made at Longshore went to lunch at Onion Alley with my friends and ice cream at Ben & Jerrys.
As I got older, I went to high school at Fairfield Prep but remained faithful to my Westport roots, keeping many of my friends who went to Staples and also my friends who joined me at Prep. When I went to College at Loyola University in Maryland, I was shocked that when I would tell people I live in Westport they immediately knew of it. That was my first time really understanding how well-known our town was. As many kids do growing up in town, I thought, well—I am off to NYC after college and will likely never return to Westport. I was quite wrong. While I loved life in NYC, my friends and I would constantly find an excuse to get out of the city and come back to Westport on the weekends to enjoy Compo, Longshore and a break from City life.
When COVID hit, I moved back to Westport with my wife Alex to live at home. After two years at home during the pandemic, Alex and I realized we didn’t want to leave. After a nine year career in NYC, I came back to work for my family’s real estate business, SCA Crowley, which just celebrated its 42nd anniversary in Westport.
We moved into our new home on Riverside Avenue and quickly loved our life living Downtown. Randy Herbertson introduced me to the Westport Downtown Association which after one year I was elected to become the President! Being a part of this incredible organization shed an even deeper light as to what makes this town so great. Working with the incredible merchants hosting fabulous events like Fine Arts Festival, and getting to build relationships with town officials and first responders you quickly realize what a special place Westport is.
As Alex and I now look to start a family of our own, I feel lucky to be in a place like Westport and soon carry on a third generation of Westporters. We have many of our friends, some who grew up in Westport and others who will be new, who all have visited, and they too want to be out in Westport!
There are not enough words to describe what an extraordinary place Westport is. I feel lucky to call this place home and be a Westporter.
Maxx Crowley, President SCA Crowley Real Estate &
President of the Westport Downtown Association