Southold

With its wineries and beautiful farmland, the village of Southold is at the heart of the North Fork. Like its neighboring villages and hamlets, it exudes New England charm. Southold was settled in 1640, at the same time as the South Fork's Southampton, making them the oldest towns in New York State. Southold Township originally stretched from Orient Point all the way west to Wading River, but the new western boundary was drawn in Laurel when Riverhead Township was created. Southold Township today comprises several villages, including Cutchogue, Greenport, and the eponymous Southold, where you'll find the town hall.

Back in 1757, a young surveyor from Virginia, George Washington, recommended that a lighthouse be built off Cliff Lot to assist sailors who had to face the perilous glacier boulders just below the surface of Long Island Sound's Deadman's Cove. This lighthouse still stands atop a 110-foot bluff.