In 1640, a group of "straitened" English pioneers left the town of Lynn in the Massachusetts Bay colony in search of land and a better life. They thought they had found it when they reached a pleasant cove on the northwestern coast of Long Island (believed to be the site of the present-day city of Oyster Bay). As far as they knew, this land fell under the patent of the English Lord Stirling, and so they entered into an agreement with the aristocrat's agent for them to found a community. What they didn't understand was that the Dutch claimed the whole of Long Island, and when news of their settlement made its way back to New Amsterdam, the director, Willem Kieft, sent a contingent of soldiers to the spot. After an altercation, the Dutch imprisoned some of the Englishmen, convincing the settlers to try another place. They moved further east, and established a community, which they named Southold-the first European settlement of what would become Suffolk County. Soon other English villages-Southampton and East Hampton-sprang up, and the English takeover of eastern Long Island was under way.
When Petrus Stuyvesant took office as the new director-general of New Netherland in 1647, he was alarmed at the incursions the English had made on Long Island. In some places his predecessor had invited English settlers, making them swear an oath of loyalty to the Netherlands. But as tensions between the two nations rose, culminating in the first Anglo-Dutch War of 1652-54, Stuyvesant didn't put much faith in those oaths. Indeed, throughout the rest of the lifetime of New Netherland, the "East Riding," as English residents of eastern Long Island referred to their territory, did its best to maintain the illusion that it was a part of England.
The town of Southold would have one moment of glory in its long standoff with the Dutch. In 1673, nine years after the English takeover of New Netherland, the Dutch staged a surprise maneuver and retook control of the province. Dutch warships sailed into New York Harbor and won control of New York City. But when a Dutch ship sailed out to the eastern end of Long Island to force its residents to swear loyalty to the Netherlands, the residents of Southold opened fire on it. After an exchange of gunfire, the Dutch ship sailed off, its mission a failure. Fourteen months later, the Dutch recapture of the province was over as well.
Biographies of the English founders of Southold
The East Hampton Historical Society
The Shinnecock and Montauk Indians
The Mill House Inn, a Bed-and-Breakfast in East Hampton