Greenport

A fleet of commercial fishing boats still operates out of this down-to-earth, working-class village, but shops and restaurants have grown increasingly upscale due to an influx of summer visitors and second-home owners. Since the late 1600s, Greenport's saga—which includes a brisk rum-running business during Prohibition—has depended on the sea. In summer the deep waters of Long Island Sound still summon home tall ships reminiscent of the whaling boats that once docked in the safe waters of Greenport Harbor. Waterfront Mitchell Park is the perfect place to watch yachts and sailboats, or to catch an outdoor performance in the landscaped amphitheater.