Located on the south shore of the North Fork of Long Island, Greenport fronts the Peconic River and Greenport Harbor. The village, set within the town of Southold, sprawls in a haphazard jumble geographically and even nearly touches the northern coast of the North Fork. Greenport’s diminutive size (little more than a square mile) belies its history, which looms large and is especially colorful. Settled in 1682, Greenport has known whaling, ship building, and Prohibition-era rum running. With more than 200 buildings dating from 1750, the village’s historic district is on the National Register of Historic Places. Perhaps more than any other North Fork town, pretty Greenport has prestige and pedigree: The village is lively, thriving, and sophisticated by area standards, but it still maintains its laid-back appeal.