Cutchogue, NY [Neighborhood Guide]

Get to know Cutchogue

Resembling the shape of a top hat with an arrow jutting south into Little Peconic Bay, Cutchogue is a hamlet in the town of Southold, on Long Island’s North Shore. Bordered by Mattituck to the southeast and Peconic to the northwest, Cutchogue was once upon a time inhabited by members of the Algonquin tribe. Settlement by the English came early; the hamlet boasts the Old House, which dates from around 1699 and is one of the oldest and best-preserved houses in the United States. The hamlet was the stomping grounds of none other than Albert Einstein, who was enchanted by the area. No wonder: With picturesque ponds and a prime position on Long Island Sound, Cutchogue is a lovely spot to settle down in.

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Cutchogue Commerce & Culture

Some Gatsby-esque homes grace Nassau Point and the bluffs overlooking the Sound, but locals regard Cutchogue as the un-Hamptons — a quiet place where half the land is dedicated to agriculture, from orchards to vineyards. Residents sail, kayak, or head to Southold’s many beaches. The few dining venues that dot modest Main Road include myriad sit-down restaurants and the adorable Cutchogue Diner, which opened its doors in 1941. This is the place to grab a stool at the counter and sit back in time to enjoy meatloaf, fried flounder, and a slice of homemade pie. Rural sophistication — on the North Shore, that’s not an oxymoron — can be found at McCall Wines, an eco-friendly purveyor complete with a tasting room and a cattle ranch.