Drumlin Does It The Old-Fashioned Way

Fred Cantor graduated from Staples High School in 1971. After Yale University he got a law degree, married, and worked and lived in New York.

But his heart was always in Westport. He and his wife, Debbie Silberstein, bought a place here for weekends and summers. Then they moved in fulltime.

It’s a decision Fred never regretted — in part because of his close-knit neighborhood.

That friendly spirit remains. Fred reports:

Fred Cantor (Photo/Lynn U. Miller)

My family moved to Westport in 1963, when I was in 4th grade, and I have many fond memories of my childhood here. Our home was on Easton Road. I spent many afternoons and weekends playing and/or hanging out with friends on nearby Silverbrook. It was a true neighborhood — at least for kids.

I know a number of “06880” readers lament some of the changes in town in the decades since that time. But I can attest that the small-town, neighborhood feeling is alive and well on the street my wife and I have lived on for the past 20+ years: Drumlin Road.

One prime example: This past weekend we had our annual road barbecue. Close to 50 residents turned out.

The ages ranged from 91 to just under 2 years old. Homeowners who lived on Drumlin since the mid-1950s chatted with a family with young daughters, who moved here just a few months ago.

Every household brought a dish (many were homemade).

Generations mixed (and ate) together at the Drumlin Road party. (Photo/James Delorey)

The friendly interactions during the party reflect the year-round atmosphere.  It’s not unusual to see residents helping out each other out. One man put his new snowblower to use in a winter storm, clearing the sidewalks of his elderly neighbors.

One of my favorite sights is seeing kids come off the school bus and — believe it or not — not stare down at their iPhones but instead talk and mess around with their friends or siblings as they head up the street to their homes. Later in the afternoon, they kick a soccer ball in the front yard, or shoot a basketball in the driveway.

Kids had a great time too at the neighborhood event. (Photo/James Delorey)

Perhaps the size of the lots — 1/4 acre — and the horseshoe shape of the road contribute to the neighborly character of the street. Whatever the reason, my wife and I feel fortunate to have lived more than 2 decades in a place that — to borrow from the slogan of the old Westport Bank & Trust — is truly a small-town neighborhood in a town of homes.

All ages posed for this Drumlin Road party photo, by James Delorey.

3 responses to “Drumlin Does It The Old-Fashioned Way

  1. the Drumlin Rd neighborhood is a wonderful example of what Westport is all about!

  2. I meant to add that 8 or so Staples alums have moved onto the road, and a former resident who rented here years ago recently bought a home on the street, which I think also says something about the appeal of Drumlin.

  3. We’ve been doing the same thing on Ledgemoor Drive for many years.We need to start taking a group photo too! So nice.

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