Compared to its more pastoral North Fork neighbors, this picture-perfect seaside village can feel like the life of the party. Greenport carries name-brand recognition for all who venture out east. It’s lively and thriving yet maintains an unmistakable laid-back appeal. A maritime community throughout its existence, Greenport made its mark in whaling, shipbuilding, and other water-borne industries. In 1844, it became the eastern terminus of the Long Island Rail Road, which operated through service to Boston via ferries to Connecticut from its deep-water docks. Today's harbor welcomes mostly recreational vessels, along with the North Ferry to Shelter Island. Over 250 buildings — dating as far back as 1750 — comprise Greenport’s historic district, displaying an impressive chronology of American residential architecture, including Italianate, Colonial Revival, and Bungalow-style homes. Exacting guidelines keep these eye-catching structures timeless throughout generations of Greenport residents and visitors.