Don't be tempted to simply pass through Southold on your way to its next-door neighbor, Greenport, because its wineries, restaurants, outdoor activities, and hotels make it a destination in itself, perfect for a low-key, relaxed getaway. The wineries are set amid beautiful farmland, and the village 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.