Fortress of Louisbourg
Whittemore was born in Charlestown, Massachusetts, in 1696, the second son by that name of Samuel Whittemore and Hannah Rix, also of Charlestown. He served as a private in Col. Jeremiah Moulton's Third Massachusetts Regiment, where he fought in King George's War (1744–48). He was involved in the capture of the French stronghold, the Fortress of Louisbourg in 1745. He moved to Menotomy, Massachusetts (present-day Arlington). Recent sources suggest he fought in the French and Indian War (1754–63) at the age of 64, once again assisting in the capture of the Fortress of Louisbourg, and later in a military expedition against Chief Pontiac in 1763. None of them offer documentation to support such claims, though a nineteenth century reference mentions that he had served as a "Captain of Dragoons."