Whittemore was born in England. He came to North America in 1745 as an officer in the British Army, where he fought in King George's War. He was involved in the capture of the French stronghold, Fort Louisburg. After the war he stayed in the colonies, settling in Menotomy, Massachusetts (present-day Arlington). He subsequently fought in the French and Indian War at the age of 64, once again assisting in the capture of Fort Louisburg.
On April 19, 1775, British forces were returning to Boston from the Battles of Lexington and Concord, the opening engagements of the war. On their march they were continually shot at by colonial militiamen. Whittemore was in his fields when he spotted an approaching British relief brigade under Earl Percy, sent to assist the retreat. Whittemore loaded his musket and ambushed the British from behind a nearby stone wall, killing one soldier. He then drew his dueling pistols and killed a grenadier and mortally wounded a second. By the time Whittemore had fired his third shot, a British detachment reached his position; Whittemore drew his sword and attacked. He was shot in the face, bayoneted thirteen times, and left for dead in a pool of blood. He was found alive, trying to load his musket to fight again. He was taken to Dr. Cotton Tufts of Medford, who perceived no hope for his survival. However, Whittemore lived another 18 years until dying of natural causes at the age of 98.
Samuel Whittemore Monument is located in Arlington, Massachusetts.
In 2005, Samuel Whittemore was proclaimed the official state hero of Massachusetts and his memory is commemorated on February 3rd each year.[1