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. Maritime endeavors have defined Greenport’s existence, as the village made its marks in whaling, shipbuilding, and other waterborne industries. In 1844, Greenport 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.