SoutholdBeginnings: Puritans from the New Haven colony founded the hamlet of Southold in 1640 after acquiring title to the land from Orient Point to Wading River from the Corchaug Indians, who called the area Yennecott. The Rev. John Youngs left New Haven with his followers in October, 1640. Eventually, the Indians, who were not hostile, were forced out of the area or enslaved.

Because almost every commodity had to come in or out by boat, shipping developed into a large industry by the 1670s. Two decades later, it had become so big, Thomas Dongan, the governor of New York, began requiring every boat sailing out of Southold to first report to New York to clear customs. Dongan dispatched a ship to the hamlet to enforce the regulation, but his captain proved amenable to accepting bribes. Shipping remained an important industry until the railroad arrived nearly two centuries later.

The Revolution: Many Southolders remained loyal to the crown, but almost half fled to Connecticut. From 1776 until the war ended in 1783, the British occupied the town, transferring the seat of government to Mattituck to better control the population. The Redcoats closed churches, plundered grain and horses, and chopped down trees for firewood.

In 1777, Lt. Col. Jonathan Meigs led 170 Continental soldiers across Long Island Sound and through Southold in his successful raid on the British garrison at Sag Harbor. Jared Landon, later the first surrogate of Suffolk County, was imprisoned by the British after a Tory alleged he had guided the raiders. The Tory, Parker Wickham, who was also the town supervisor, was later declared a traitor and banished from the state. After the British left, many of the refugees returned. But the economy remained in ruins even as a second war with Britain broke out in 1812. The British sent foraging parties ashore and established a blockade of the East End, but it was so porous, most ships were able to sail to and from New York unmolested.

Turning Points: After Greenport was incorporated in 1838, it became a prosperous whaling center and attracted much of the shipping and shipbuilding industry that had been centered in the hamlet of Southold. More changes came with the arrival of the Long Island Rail Road in 1844. Trains now carried farm products to market in the city and returned with tourists for new hotels and boarding houses. But the community remained primarily agricultural. There was already a long history of horse racing when Southold became the home of large breeding farms in the 19th Century.