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Get to know Greenport

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, ship-building, 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 — make up Greenport’s historic district, displaying an impressive chronology of American residential architecture that includes Italianate, Colonial Revival, and Bungalow-style homes. Exacting guidelines keep these eye-catching structures timeless throughout generations of Greenport residents and visitors.

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Greenport Commerce & Culture

While you could spend days simply reading the historic plaques, there is much more to the Greenport experience. Head to Mitchell Park near the waterfront for attractions that include a bustling marina, an ice skating rink, an antique carousel, and ample lawns. During Prohibition, rum-running and speakeasies were a vital part of Greenport’s economy — residents knew the waters so well they could smuggle anything without detection. Nowadays, alcohol plays a far more licit role in bolstering this village with beloved craft breweries, distilleries, and wineries. There’s farm-to-table cuisine, a historic waterfront restaurant with centuries of provenance, happening spots featuring seasonal menus, and — of course — delectable seafood. Front Street and Main Street run perpendicular to each other and house much of Greenport’s commerce — from shops selling furniture, books, and vintage clothes to an Art Deco movie theater. Ferry service can connect you to the enchantingly idyllic Shelter Island in under 10 minutes.