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Stamford: Shippan — Gateway to the Sound



On a clear morning, mist rises over Dolphin Cove on Shippan Point and, like Brigadoon, the New York City skyline appears, shimmering in the distance. Offshore, otters are at play; an egret swoops down to catch a fish for breakfast and seagulls exchange raucous cries. Against a blue sky, cattails wave in the breeze. On the beaches horseshoe crabs scuttle, seashells wait to be discovered and the sand is made for building castles. It’s a little bit of paradise, five minutes by car from the Stamford train station.

Dolphin Cove is just one of several beaches on Shippan Point, a delightful part of the city of Stamford. The peninsula, which juts out into Long Island Sound, was purchased in 1640 from Native Americans by English settlers who farmed the land. In the late nineteenth and the twentieth centuries, its coastline attracted the attention of wealthy New York City businessmen with a passion for sailing. The two yacht clubs formed in that early era, Stamford Yacht Club and Halloween Yacht Club, still thrive today and continue to be hubs of Shippan social life. 

Today’s version of community, while still water-oriented, is all about being neighborly. It’s what makes this completely residential enclave so special, the kind of place where instead of moving out, people move from house to house.

“We call it doing the Shippan shuffle. It’s not unusual for a family to have lived in four or five different Shippan homes over the years,” says Gail Malloy, a local Realtor whose own extended family is happily settled on the peninsula. Of seven Malloy brothers, six are Shippan residents, including her brother Dan, the current mayor of Stamford.

From quarter-acre and half-acre lots to much larger waterfront properties, Shippan is a wonderful mixture of sizes and styles. Large houses sit next to small cottages, and it all works. A walking tour might include several notable homes. The house at 141 Stamford Avenue was given as a wedding gift to a Rockefeller niece, and 34 Saddle Rock Road was built at the height of the Roaring Twenties by Charles Davenport Lockwood, a founder of Stamford’s Cummings and Lockwood law firm. European artisans were brought in to lavish attention on every single detail. The house is still extraordinary today.

Over the years Shippan was home to the family of the Gillespie brothers, publishers of the Stamford Advocate. That house no longer exists today, but the one at 75 Rogers Road that belonged to the family of United States Congressman Schuyler Merritt, who chaired the commission that created the Merritt Parkway, is still there. Moira Lyons, former speaker of the Connecticut House of Representatives, currently lives at 37 Ocean Drive West. And actress Faye Dunaway and singer Harry Connick Jr. used to call Shippan home.

Architecturally, it’s a comfortable hodgepodge. Whether a converted barn moved from one of the original estate farms, a venerable 1875 Queen Anne Victorian or more modern variations on Tudor and Mediterranean styles, nothing seems intrusive — not even Marion Castle at 1 Rogers Road, completed in 1916 and built in the style of a French chateau by European craftsmen. Listed on the National Register of Historic Places, it is currently a private home, often made available for community functions by its owner.

According to residents, it’s a good bet that the people inhabiting the houses relate to one another the good old-fashioned way. Some are satisfied with just a wave hello. But most want more of a connection, and they find it through neighborhood organizations like the Shippan Point Gourmet Club, Shippan Point Garden Club or Shippan Point Association.

Unlike Rowayton, a waterside community in nearby Norwalk, there is no central village, but Shippan Avenue offers restaurants, grocery shopping, and a major art and antiques center. “The city is very accessible, but I feel like we live in the country,” says Susan Flynn, president of the Shippan Point Garden Club and an at-home mother of two who moved from East Haddam, Connecticut, eight years ago. “It was easy to meet people,” she says, adding that the local clubs have multigenerational memberships, which create an additional sense of family. 

On a sunlit spring morning, children’s laughter mixes with birdsong. This is the ideal “it’s safe to send your kids out to play” neighborhood — a big plus for the area’s many young families. The occasional car goes by, as do joggers who seem to enjoy the scenery and conviviality as much as the exercise.

A woman out walking stops a friend to pass along the happy news that a neighbor just had triplets. Shippan attracts a lot of individuals who share an interest in each other and in their community. Residents include businesspeople, academics, bankers, diplomats and artists. Multicultural and international, people are refreshingly different.

On many streets, Long Island Sound is visible at either end. You can’t walk very far in any direction without falling into the water, but it’s more than just the view. The peninsula has been described as having its own temperate zone. It’s warmer in the winter and a bit cooler in the summer. Even the fall foliage lasts longer.

Although summer is here, Susan can’t resist mentioning a winter tradition — the Doors of Shippan competition. Sponsored by the garden club every Christmas, the contest challenges residents to decorate their front doors according to specific guidelines. The results reliably attract attention from other parts of Stamford and beyond. “It’s a local holiday tradition,” Susan says, “definitely a reason to drive by and take a look.”

Betsy Levinson, a very energetic new grandmother, is someone who drove by and decided to stay. After living in the woods of North Stamford for thirty-four years, she had begun to feel isolated. “Moving here was like moving to a different continent,” she says of her house on the water. “Shippan Point is its own resort. It’s a fabulous fishbowl. Everybody’s out and about.”


A visit to Shippan Point, whether for shopping,eating or just breathing the salt air, offers the perfect opportunity to unwind from the hustle and bustle of downtown. Here are a few places you might not want to miss.

Agabhumi, the Best of Bali
22 McGee Avenue; 325-2274
“In translation Agabhumi means ancient earth,” say Regina and Mike Kirshbaum, Shippan residents who fell in love with Bali on a visit years ago and decided to bring the magic back to Connecticut. Check out the exquisite Indonesian jewelry and exotic home furnishings.

Center for Arts & Antiques
614 Shippan Avenue; 353-0222
They buy,  they sell and they take on consignment at this international design source with more than 125 dealers ready to offer the finest antiques and contemporary art at wholesale prices. AGA certified appraisers on site.

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