Issachar Andrews came to Carlisle with their father Solomon and brother Edmund from Ipswich on ox sleds during the frigid winter of 1765. The family purchased a three-hundred-acre tract of land near the Concord River where they cleared a small farm and built a homestead and fulling mill. In the 20th century, this historic farm would become the Greenough Conservation Land.
Issachar is said to have participated in the Concord Fight on April 19th 1775. He was the first Lieutenant in Captain Samuel Heald’s company in Colonel Francis Faulkner's 3rd Middlesex County Regiment. On Feb 4, 1779, he was commissioned an officer, and he later became Captain. Issachar was very active in town affairs serving as Selectman. As the war was coming to an end, he was one of the residents chosen to serve on a five member committee to recruit local boys to join the Continental Army.
in 1780, Issachar was appointed one of the District's Tythingmen. One of the main responsibilities of the Tythingmen were to maintain decorum at Church services and Town Meeting. If someone fell asleep during one of these meetings, the Tythingmen were responsible for waking them up by hitting them over the head with a stick.
Many of Issachar's his descendants would also go on to help shape our community’s development in countless ways. These include Waldo Wilson, Carlisle’s first fire chief.
Issachar Andrews is buried in Carlisle's Central Burying Ground.