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.