Old Saybrook is a town in Middlesex County, Connecticut, United States. The population was 10,242 at the 2010 census. It contains the incorporated borough of Fenwick, as well as the census-designated places of Old Saybrook Center and Saybrook Manor.

in 1624, shortly after establishing their first settlement at Governors Island, Dutch settlers established a short-lived factorij 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 English at Saybrook. During an eight-month time period, the Pequot killed and wounded more than twenty English at and near Saybrook Fort. The English were attacked when they ventured far from their palisade, and the Pequot destroyed English 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 English assessed each other's military capabilities, and adjusted counter-tactics. 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).

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