Founded in 1640, the town and hamlet of Southold, New York is considered to be the oldest English town in New York State. It’s located on the North Fork of Long Island and was the first town settled in that area. It is probably the most historic small town in New York State; if you want to know more, keep reading below!

Southold was populated by Algonquian-speaking tribes before English Puritans from New Haven Colony settled the town on October 21,1640.
Town of Southold
The town is on a peninsula called the North Fork and is separated from Connecticut via the Long Island Sound. It has 163 linear miles of coastline.
Southold Library
Southold went through a period of turmoil and change when the Dutch took over the colony of New York. After New York was retaken by the English, Southold attempted to remain part of Connecticut, though the government of James, Duke of York forced the town to be in New York. Southold yielded to the state in 1676.
Southold Library

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The town’s name is thought to be an elision of Southwold, which is a town in the English county of Suffolk where John Young—a minister and a founder of the town—was born.
Wikimedia Commons
Later in the 19th century, the Long Island Rail Road extended its line, which allowed vacationers to access Southold by train. Many artists were attracted to the town’s outstanding coastal light—among them, the American impressionist painter William Merritt Chase.
Americasroof Wikimedia Commons
For a long time, the area was mostly agricultural, with a focus on potato farming. In the late 20th century, though, many parts of the North Folk were turned into vineyards. The area currently has a thriving wine industry.
Kosboot Wikimedia Commons

Southold, New York is an amazing place with an even more amazing history. If you are interested in the story of New York State, it’s definitely worth a visit. Looking for a place to stay in this historic small town in New York? We recommend the Southold Beach Motel. And, while you are in Southold, you should consider checking out this amazing vineyard that also doubles as a hotel.

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Southold, NY 11971, USA