Tag Archives: Drumlin Road

[OPINION] That’s What (Westport) Friends Are For

Fred Cantor was a longtime Westporter. The 1971 Staples High School graduate still feels connected to this town — and our blog. Fred writes:

My wife Debbie and I are moving soon for health-related reasons from Oronoque Village, a senior community in Stratford, to a senior community in Southern California.

So we made a visit to Westport. We stopped by my childhood home on Easton Road — where Debbie and I got married in a small family ceremony in 1982 — and the home on Drumlin Road where we lived for 22 years.

Fred Cantor’s childhood home on Easton Road …

Both houses epitomized the era they were built: the 1950s. The Easton Road home was roughly 1,850 square feet. The Drumlin one was approximately 1050 square feet.

I am fortunate in that, in contrast to many childhood friends, stopping by my old stomping grounds feels almost like a step back in time. Neither home became a “Teardown of the Day.”

… and Drumlin Road, where he and Debbie lived for 22 years.

So being back there triggers a variety of memories.

But in going back, it’s not just the memories of family — many of whom are gone now — that make these places feel special.

I realize too what will always make Westport feel like my hometown are the wonderful neighbors and friends from the times I lived in these houses.

We sold our Drumlin home privately to a friend and former neighbor who was looking to return — and Debbie and I are so glad we did. Cheryl enjoys the home every bit as much as we did, and has put such loving care into the property.

When Debbie and I approached our former longtime home Cheryl, in her 60s, was out in the yard cutting the grass and mulching leaves with her very quiet electric mower. Gotta love that.

And seeing our former Drumlin neighbor, the beloved Staples teacher and administrator Gordon Hall, to wish him an early happy 98th birthday brought back memories of the various kind things he and his wife Dot — and several other Drumlin neighbors as well — did for us over the years.

 

This visit came not long after attending the boys soccer FCIAC championship match in Fairfield. I sat near my former Staples coach, Jeff Lea, former teammate Jim Bacharach, and other Staples soccer alums. This was accompanied by a flood of emails with former Staples teammates during the remarkable postseason run by the 2025 squad.

These combined experiences reinforced the feeling that there have indeed been a number of terrific friends and neighbors over the years who helped make Westport seem like I was living the story in “It’s A Wonderful Life.”

So here’s a farewell toast to all of those people who made me feel lucky to have lived for decades in such friendly and supportive small-town surroundings.

Fred Cantor and Debbie Silberstein wave goodbye. (Photo/Tracy McIntosh)

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Kenneth Walsh’s Weekend In New England

Kenneth Walsh is one of Westport native Don Willmott’s favorite bloggers.

Kenneth lives in Manhattan. But he has a strong Westport connection, through his late grandmother.

He visited here over Thanksgiving, to look into the places she lived. Then he posted photos from his tour.

Willmott calls it “a great, somewhat epic saga of family dysfunction: Westport ‘behind closed doors,’ with lots of before/after photos he took thanks to the cooperation of generous current residents.”

Kenneth and his husband Damian “rented a quirky guest house in Westport, with plans to recharge, see a couple friends (everyone we know is moving that way so we’ve become ‘Connecticut curious’),” then went on a “family-history spree” to see where his maternal grandmother spent the last chapter of her life, before dying by suicide shortly after her 50th birthday.

His long story about his family history — fascinating to people with an interest in such things — is sprinkled with photos from decades ago, and how they look today. They include Hillspoint Road opposite Old Mill Beach, and Drumlin Road.

Kenneth Walsh (right) in front of his grandmother’s former Drumlin Road house (left) …

… and 240 Hillspoint Road.

Kenneth also writes about his grandmother’s neighbor (a former colleague of Albert Einstein), the drinking culture of the town at the time, and more.

He gives a shoutout to the restaurants he and Damian visited (Basso, Spotted Horse, The Cottage, Rive Bistro), and to the “welcoming” Westport Pride rainbow crosswalk on Jesup Road.

It’s an intriguing look at our town, from an outsider who appreciates his inside connections.

Kenneth Walsh and his husband at Old Mill Beach. Decades earlier, Kenneth’s grandmother and her husband posed at the seawall there.

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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.

Neither Snow Nor …

Today’s light but steady snowfall made driving treacherous.

(Except for the usual bozos barreling along the Post Road at their usual breakneck speed. Slow down, guys!)

Our postal carriers were undeterred. They lived up to their motto — as this photo from Drumlin Road shows.

(Photo/Fred Cantor)

(Photo/Fred Cantor)

The truck made its way up the unplowed road with some difficulty, alert photographer Fred Cantor reports.

But it did deliver the mail.

1 Road, 3 Neighbors, 50 Years

In 1952, Mike and Galy Starzyk moved to Drumlin Road.

Two years later, Gordon and Dot Hall moved in across the street. Nine years after that, Bernie and Barbara Dorogusker bought a house next door to the Starzyks.

Much has happened since then. Countless families moved in, had kids, raised them, moved away. Decks were built, 2nd floors added. Trees have grown tall (and fallen).

But nearly 50 years later, all 3 families still live on the horseshoe-shaped drive near Hillspoint and Green’s Farms Road, just south of the railroad tracks (and the “Connecticut Turnpike” — I-95 — which was still being debated when the former cow pasture was developed back in 1952-53).

There may be no other place in Westport where 3 neighbors have lived so close together since the Kennedy Administration.

A 1952 ad for "Compo Manor: A Residential Community Situated in Westport, Beauty Spot of Southern Connecticut" shows "The Perfect Three-Bedroom Rancher" model home. It is "Priced at $14,500. Complete."

The Starzyks are the only original owners left. Mike and Galy were living in Bridgeport. With 2 children, they needed more room. Galy’s brother-in-law — Art Reale — told them about a new development, “Compo Manor.” The lots were small — 1/4 acre — but the $14,500 price was perfect.

Better yet, nearly all their neighbors were like the Starzyks: young, and with kids.

In 1955, Gordon and Dot Hall’s daughter was not yet born. Married 2 years, and both teachers — he at Bedford Junior High School, she at the brand-new Coleytown Elementary — they had rented “tiny, ramshackle places” elsewhere in town.

But they saved their pennies — “literally,” Gordon notes — and loved the little ranch house that was for sale. Other tract homes they’d seen — on Reichert Circle, Bauer Place and Tamarack — all faced in the same direction. The 43 Drumlin homes were built with the same 2 or 3 floor plans, but they were angled uniquely. And each setback was different.

The asking price was $20,600. The Halls paid $19,600. On their salaries — he made about $3,000, she $2,900 — that was manageable. But for 4 summers, when they took graduate courses, they rented the house out. The extra cash helped make ends meet.

“There were lots of strollers, and there was lots of sledding,” Dot recalls. “Everyone was very sociable, because (the adults) were all around the same age.”

Gordon and Dot Hall's house in 1957 (left) and 2012 (right). The 3 families that have been neighbors for nearly 50 years share the mailboxes in the photo at right.

Barbara Dorogusker is the “newest” of the 3 neighbors — but she’s got the longest local connection. A 3rd-generation Westporter, she grew up on 6 acres on Sturges Highway. Her grandmother (a former indentured servant in Poland) lived next door. The property included a pond and barn.

After graduating from Staples in 1952, Barbara married a man from New York City. They wanted to buy a house, but without much land. Bernie was a sailor; proximity to the Sound was key.

With $2,000 in the bank, they searched for a while. Finally they saw a place on Drumlin. With a big field in back — off Jennie Lane — they could look at nature, but not have to take care of it.

“It wasn’t our dream house,” Barbara admits. “But every house is a compromise.”

Her parents were “appalled. They thought we  were moving into tomorrow’s slums because the lots were so small.” But, Barbara says, “it was perfect for us.” And Cedar Point Yacht Club was just down the hill, at Compo Beach.

They built a big sunroom, and a deck. They had 2 children. “We wanted them to grow up surrounded by friends,” Barbara says. “They sure did.”

The kids created secret pathways between bushes. An empty school bus would pull up to the foot of Drumlin Road. It drove away filled.

Every summer, the Drumlin Road neighbors have a block party. Last summer's event showed an enormous span of ages -- but plenty of smiles.

Over the years, the road changed. There were many “older couples, divorced people, one-child families,” Gordon says.

Miraculously for Westport, there have been only 2 demolitions — and both were caused by accidents. One house burned; the other had a tree fall on it.

Of course, many homes have been remodeled. They’re a bit larger than they were (Gordon calls them “mini-mansions, not McMansions”). So they’re once more attractive to young couples. “We’re seeing bicycles and strollers again,” says Dot.

But not every house has been sold, re-sold, and re-re-sold.

“Why would we ever want to move?” Barbara asks. “Everyone looks out for each other here. We’ve got one story, which is great.” (She’s 77; Bernie is 85.)

“And with housing prices going to pot, why leave?”

Similarly, after the Starzyks’ kids grew up and moved away, Mike and Galy stayed. “We were comfortable,” she recalls. “There was no reason to leave.”

Sixty years later, they’re still on Drumlin Road.

“I don’t know how much longer I’ll be in this world,” 93-year-old Galy says. “But I have no plans to move.”

Nor do her neighbors. After 49 years together, there’s no place like home.