Southold

Algonquian-speaking tribes, closely linked to those found in New England across Long Island Sound, inhabited eastern Long Island before the arrival of European settlers. Meanwhile, the western region of the island was home to bands of Lenape, whose language also belonged to the Algonquian family.

In the surrounding areas, Dutch colonists had established early settlements to the northwest: Fort Orange, founded in 1615 (later renamed Albany by the English), stood on the upper Hudson River, while New Amsterdam (later renamed Manhattan) was established in 1625. Lion Gardiner established a manor on Gardiners Island in East Hampton in 1639. Just across from Long Island, the Connecticut Colony, or Connecticut River Colony, emerged in 1636. Despite being largely surrounded by Connecticut Colony, the Puritans separately established New Haven Colony in 1638, operating as a theocracy governed solely by church members.

English Puritans from New Haven Colony settled in Southold on October 21, 1640, after purchasing land in the summer of the same year from a group of Native Americans related to the Pequot of New England, who resided in the area they called Corchaug (now Cutchogue). Initially spelled “Yennicott” by settlers, Southold is widely recognized as the first English settlement on Long Island within what would become New York State. Under the leadership of Reverend John Youngs and Peter Hallock, the settlement consisted of families including Barnabas Horton, John Budd, John Conklin, John Swazy, William Wells, John Tuthill, and Matthias Corwin.

In 1650, the Treaty of Hartford established a boundary between Dutch and English claims, roughly passing through Oyster Bay on the North Shore. The Dutch controlled the western part of Long Island, while the English dominated the east. At that time, Southold’s population was approximately 180. The harbor at Greenport, located on the North Fork, grew in importance for trade, fishing, and whaling, particularly because it seldom froze over. Settlers also developed the interior land for agricultural purposes.