A recent research inquiry to the academy’s Archives prompted me to do some investigation into the issue of race integration throughout the school’s history. The research brought me back to the earliest years of the school, when Preceptor (Headmaster) Samuel Moody started his first lessons at the Little Red School House on March 1, 1763. Among the first class of 28 students under Moody was Wentworth Cheswell, a 16-year-old from Newmarket, New Hampshire.
While a formal education was a luxury in the 18th century, what is particularly notable about Wentworth Cheswell’s attendance is that he was accepted, and indeed thrived, at the academy with apparently little concern for his family being multiracial: Wentworth’s father was the famous housewright Hopestill Cheswell—himself the son of a freed black slave and a white woman—and Catherine (Keniston) Cheswell, who was also white. Hopestill’s father, Richard Cheswell, was a black slave in Exeter New Hampshire, who earned his freedom and, in October 1717, purchased 20 acres of land in what is today Newmarket. The transaction represents the earliest known deed in the State of New Hampshire showing ownership by a black man. Hopestill had his own significant achievements, having built several notable structures, including the John Paul Jones House, a National Historic Landmark which today houses the Portsmouth Historical Museum, and the Samuel Langdon House, which is now located at Sturbridge Village. Wentworth Cheswell’s education at Dummer Academy allowed him to achieve many professional successes himself.
After Wentworth Cheswell completed his studies at Dummer Academy, he returned to Newmarket to become a school teacher, but soon became embroiled in the American Revolutionary War. He was elected town messenger for the regional Committee of Safety, one of the many groups established in Colonial America to monitor events pertaining to public welfare. During the American Revolution, these committees communicated with Committees of Correspondence, which disseminated information along the militia units and provided intelligence on British activity. When Paul Revere rode to Portsmouth to alert defenders to the impending arrival of the British frigate Scarborough and the sloop of war Canseau, Wentworth Cheswell, as town messenger, rode on to Exeter to help communicate instructions on where militia men were to be sent. As an enlisted man, Cheswell served under Colonel John Langdon in the Company of Light Horse Volunteers at the Saratoga campaign.
Upon his return to Newmarket, Wentworth Cheswell settled into a long and prosperous life. He and his wife went on to have 13 children, and he remained an active and vibrant part of public life in New Hampshire. He was active in public office, holding positions as a school regulator and Justice of the Peace for Rockingham County.
