Most of my life, I was a Manhattanite. I’m 55 and if I do some rudimentary math it breaks down like this: 15 years in Westport (two in high school, 13 as an adult), three years in Greenwich (which I can’t remember, because I was a toddler), about two years in Dallas (but I was traveling for work most of the time), one year in Westchester as a high school sophomore, and the other 33 years in Fun City (a semi-ironic nickname for New York City popularized by my father, Dick Schaap). Like a lot of transplants to the suburbs, I miss the energy of New York, more than the museums or the theater or any of the other cultural attractions, which frankly I did not avail myself of as much as I could have (who does?). And I miss walking to get somewhere.
As for Westport, I love it. Which feels a little weird to confess because I still think of myself as a New Yorker, and a New York loyalist. Let’s face it. It takes a long time to let go of the city. But my wife and I did not end up here raising our family by accident, or on a whim. We knew the town. After all, I am a Staples High School graduate (class of 1987)—and we spent a lot of time when we were still living in the city imposing on our friends who lived out here, namely Joe and Debbie Valerio, of Minuteman Hill, especially on hot summer weekends. Westport also happens to be halfway between midtown Manhattan and the headquarters of my employer, ESPN, in Bristol, Ct. From Westport, you can be in Bristol in about 50 minutes, which explains why you see so many sports tv people in these precincts.
So we never really considered anywhere else. Which was a good decision.
Why? There is the stuff we all know about, important stuff, especially the school system, which has impressed us tremendously. I have never met Tom Scarice, Westport’s superintendent, but I was awed by the job he and all of our educators did during the worst days of the pandemic, keeping the kids safe and at the same time emphasizing the importance of in-school education. The Schaaps are going into our ninth consecutive year in the school system. Then there are the beaches (especially Burying Hill), Longshore (including the skating rink) and the playhouse, riding bikes down around Saugatuck Shores, the incredible Westport Public Library and Bedford Family YMCA, the worthy and usual suspects.
(Do I miss some of the things that have vanished? Naturally. Back in the mid-‘80s, there were all those bookstores on Main Street, including Remarkable and Klein’s, and there was Hay Day. The great Allen’s Clam House is now a park, which I guess is ok.)
But what really makes Westport special for me are the people around town I have come to know. Living for nearly a quarter century just north of Times Square, in one of the busiest neighborhoods on planet Earth, I knew some of the local characters, but on any given day I might not have occasion to speak to a single person with whom I was actually acquainted. Here in Westport, it is rare for me, and probably for you, to venture out of the house without encountering someone you know. When we moved here, frankly I thought that would be a negative. In the city, we put a premium on privacy. But now I look forward to the stop and chats, all the bonhomie, at Coffee ‘n’, or Colonial Druggist, or Gold’s, or Stiles’, or Saugatuck Provisions, or the UPS store, or Westport Hardware, in other words the most indispensable institutions in town.
Yes, when I think of what I treasure about Westport, I think about Stacey and Elias of Coffee ‘n’ fame—even though, as a Mets fan, it can be tough to be around Elias after a big win for the Yankees. I think about Nancy, the Knicks fan who presides over the counter at Gold’s, which I would stack up against any of the smoked fish emporiums of Gotham. I look forward to chatting with Paul, king of butchers, who has made a triumphant return to Saugatuck. The whole crew at the UPS store across from Fresh Market is incredible. They could have planned the invasion of Normandy. And who doesn’t love Anthony at Stiles’ Farmers Market? We all depend on the cutlets.
But if Westport handed out an MVP award, my first place vote would go to Russell Levine, the nonagenarian pharmacist/irrepressible wit/inveterate whistler. Russ has been working in Westport since the early 1950s and he hasn’t taken a vacation since the first lunar landing. The sign on the door says that Colonial, his pharmacy, closes at 6 pm, but everyone knows that Russ will still be there long after 6, closer to midnight. My wife and I were ignorant of the excellence of Colonial until our pediatrician urged us to move on from the chain where we were customers. That was great advice. Dr. Marc Oestreicher, another of my local favorites—also a Yankees’ fan, but he’s from the South Bronx, so he gets a pass—calls Russ a giant. He would know. And I concur. They should erect a statue of Russ—and put it right there in the Colonial parking lot. There should be a big button on it. Press it, and the statue starts whistling, slightly but winningly off tune.