Old Saybrook is a town in Middlesex County, Connecticut, United States. Its population was 10,481 at the 2020 census. It contains the incorporated borough of Fenwick, and the census-designated places of Old Saybrook Center and Saybrook Manor. History In 1624, shortly after establishing their first settlement at Governors Island, Dutch settlers established a short-lived factory at present-day Old Saybrook. The trading post was named Kievits Hoek, or "Plover's Corner". Kievits Hoek was soon abandoned as the Dutch consolidated settlement at New Amsterdam. In 1633, Fort Goede Hoop (Huys de Goede Hoop), was established at present-day Hartford. The Pequot siege of Saybrook Fort took place from September 1636 to March 1637 during the Pequot War. Following the August 1636 Massachusetts Bay attack on Manisses, Pequot, and Western Niantic villages, the Pequot retaliation fell on the settlers at Saybrook. During an eight-month time, the Pequot killed and wounded more than 20 settlers at and near Saybrook Fort. The settlers were attacked when they ventured far from their palisade, and the Pequot destroyed their provisions and burned warehouses while they attempted to interrupt river traffic to Windsor, Wethersfield, and Hartford. During the Siege and Battle of Saybrook Fort, the Pequot and New England colonists assessed each other's military capabilities, and adjusted countertactics. Each side's tactical modifications show a high degree of sophistication, planning, and ingenuity. Lessons learned during the siege of Saybrook escalated the Pequot War in Connecticut Colony, and indirectly resulted in the attack and destruction of Mistick Fort (May 1637). The Saybrook Colony was established in late 1635 at the mouth of the Connecticut River, in what is today Old Saybrook and environs. John Winthrop, the Younger, son of the Governor of the Massachusetts Bay Colony, was designated governor by the group that claimed possession of the land via a deed of conveyance from Robert Rich, 2nd Earl of Warwick. Winthrop was aided by Colonel George Fenwick and Captain Lion Gardiner. As the principals of the group who had planned to settle the colony were supporters of Oliver Cromwell and remained in England during the English Civil War, the colony struggled. In 1644, Fenwick agreed to merge the colony with the more vibrant Connecticut Colony a few miles upriver, which purchased the land and fort from him. The design of the Flag of Connecticut comes from the seal of Saybrook Colony. The seal was brought from England by Colonel George Fenwick,