EDIT-Southold.indd The hamlet of Southold was settled in 1640 by English Puritans from New Haven Colony in Connecticut. It is reported to be the first English settlement on Long Island and the oldest English town in New York State. Celebrating its 350th birthday in 1990, it will celebrate its 375th birthday in 2015! A quaint village surrounded by farms, vineyards, and beaches, with Long Island Sound to the north, Southold Bay to the east, and Little Peconic Bay to the south, it is ideal for summer vacationers, retirees, and full-time residents alike.