Wentworth Cheswell (11 April 1746 – 8 March 1817) was an American assessor, auditor, Justice of the Peace, teacher and Revolutionary War veteran in Newmarket, New Hampshire. Elected as town constable in 1768, he was elected to other positions, serving in local government every year but one until his death.

Some sources consider Cheswell to be the first African American elected to public office in the history of the United States, as well as the first African American judicial officer. Others are less sure, noting he was biracial and recorded as "white" in censuses.

Wentworth Cheswell

Around the time of his marriage, Wentworth purchased a plot of land from his father Hopestill. His grandfather Richard is believed to be the first African American in New Hampshire to own land. A deed shows that Richard purchased from the Hilton grant in 1717. In 1801, Wentworth was among the founders of the first library in the town and provided in his will for public access to his personal library.

Wentworth Cheswell

Early life and education

Wentworth was the only child born in Newmarket, New Hampshire, to Hopestill Cheswell, a free black man of biracial ancestry, and his wife, Katherine (Keniston) Cheswell, a white woman. The senior Cheswell was a master housewright and carpenter who worked mostly in the thriving city of Portsmouth. Among other projects, Cheswell helped to build the Bell Tavern on Congress Street and the John Paul Jones House, originally owned by Captain Gregory Purcell and now a designated National Historic Landmark. The Jones house was an example of classic mid-eighteenth century elite housing. The Jones House for years served (and continues to) as the Portsmouth Historical Society Museum. Cheswell also built the Samuel Langdon House, which was moved to Sturbridge Village; it is a central exhibit demonstrating 18th-century construction technology.

Wentworth Cheswell

Hopestill Cheswell was born free to a white mother and Richard Cheswell, an indentured black laborer in Exeter, New Hampshire, who was the first Cheswell recorded in New England. (Because his mother was free, the boy was free, according to the principle of partus sequitur ventrem, by which children followed the mother's status, which was incorporated into slave law in the colonies.) After completing his servitude, Richard Cheswell purchased of land from the Hilton Grant. The deed, dated 18 October 1717, is the earliest known deed showing land ownership by a black man in present-day New Hampshire. The land was located in what was to become the town of Newmarket. Hopestill was the only known child of this union.

Hopestill Cheswell earned enough as a housewright to purchase a total of more than of land between 1773 and 1749, which he farmed while working as a housewright. Later, he had part ownership of a sawmill and stream in Durham, New Hampshire, as well as "mill privilege" at another falls, to handle his need for lumber. His prosperity helped provide for his son's education.

He sent his son Wentworth to Governor Dummer Academy in Byfield, Massachusetts. There the youth studied with the Harvard graduate William Moody, who taught the classical subjects of Latin and Greek, reading, writing, and arithmetic, as well as swimming and horsemanship.

As Erik Tuveson noted in his master's thesis on the first three generations of Cheswells, the youth's education was: an unusual privilege for a country boy of that time. Few people of the colonial era were formally educated, mostly due to cost and lack of inexpensive public schooling. Education of any formal sort in colonial New England carried a significant degree of elite social status.

Early career

After completing his education, Wentworth Cheswell returned to Newmarket to become a schoolmaster. In 1765, he purchased his first parcel of land from his father. By early 1767, he was an established landowner with more than and held a pew in the meetinghouse. By 1770, he owned .

Cheswill was first elected to public office in 1768 as the town constable, and later was elected to local offices every year (except for 1788) until his death in 1817, to positions such as town selectman, auditor, assessor, and others. In 2008, George Mason University in Virginia declared Wentworth Cheswell to be the first African American elected to public office in the history of the United States. He preceded Alexander Twilight of Vermont (1836), Joseph Hayne Rainey of South Carolina (1870), and John Mercer Langston of Virginia (1888) for the title.