Isaac Wilkins, according to local tradition, fought in the Battle of Lexington and Concord along with his slave, a black man named Toby. Toby supposedly was killed during the day’s fighting, somewhere along battle road. Issac later served in the Battle of Fort Ticonderoga in 1776. At the time of his last discharge, Isaac had reached the rank of Lieutenant.
After the war in 1780, Wilkins served as one of the Districts' "Surveyors of Highways" overseeing the creation of new roads throughout the community, many of which still exist today. He also served on the prestigious committee tasked with hiring a minister to serve the District. In 1795, Issac constructed the stately yellow house next to the Gleason Library at 44 Bedford Road.
It is worth noting that Isaac Wilkins was among the longest-lived Carlisle patriots. He died on January 10th, 1826 at the age of 92.
Isaac Wilkins is buried in Carlisle's Green Cemetery.