Wentworth Cheswell was born in 1746 in Newmarket, New Hampshire, to a free biracial father and a white mother. He attended Dummer Academy in Massachusetts, where he studied reading, writing, arithmetic, Latin, Greek, and other subjects. His education prepared him to become a schoolteacher and an influential community leader. In 1768, Cheswell was elected town constable, a position similar to that of a police officer. That made him one of the first African Americans elected to public office in what would become the United States.
Cheswell served in many public roles, including auditor, assessor, selectman, and justice of the peace. During the American Revolution, he was elected town messenger for the Committee of Safety. This position gave him safe passage through battle lines to deliver important news. He also took part in the Patriot capture of Fort William and Mary and later fought at the Battle of Saratoga.
After the war, he returned to teaching, ran a store, and helped found Newmarket’s first library. He is remembered as New Hampshire’s first archaeologist for recording and sharing information about local artifacts. He died in 1817 at age 70. He is buried in Chiswill Cemetery in Newmarket, New Hampshire.