By Angela Matthews, for Black Heritage Trail NH

Hopestill Cheswell was born about 1712 to Richard, a Black man, and an unknown White woman. His father is believed to be the first Black person to own property in the colonies; there is a 1717 deed in his name for land in what would become Newmarket.

Though it probably was impossible for Richard’s son, Hopestill, to have apprenticed in a trade, he became a highly successful carpenter and housewright. Two of his constructions still stand in Portsmouth: the John Paul Jones House on State Street and Stoodley’s Tavern, which was moved from Daniel Street to Strawbery Banke in the 1950’s. A third building, formerly the home of Samuel Langdon, was scheduled for demolition when it was purchased by and moved to Old Sturbridge Village in Massachusetts, where it serves as the administrative building.

An enterprising and shrewd businessman, by 1749 Hopestill had amassed more than 100 acres of farmland in Newmarket and acquired part ownership of a mill in Durham and milling privileges at Wadleigh’s Falls. In these ventures, Hopestill was better able to control both the price and the quality of the lumber and building materials he put to use.

Despite his successes, Hopestill lived in a world of discrimination. For example, upon the completion of Bell Tavern on Congress Street “…there was, according to the custom of the day, a merry gathering to commemorate it. Though Hopestill had performed an important part of the work, he did not venture to approach the board, until it was decided by the company that he should be permitted to come in and partake with them on the joyful occasion.” (Brewster’s Rambles About Portsmouth) Further complicating the experience, Bell Tavern was owned by Hopestill’s half-brother, Paul March, a White man.

Hopestill and his White wife were able to send their son, Wentworth, born in 1747, to Dummer Academy, a boarding school in Massachusetts. Wentworth returned to Newmarket as a school teacher. He soon became the first Black person in the state, and probably in the nation, to hold elected office. He was elected to many offices during his life, including constable, selectman, auditor and assessor. He served in the Continental Army and, as a member of the Committee of Safety, helped Paul Revere spread the word that the British were coming.

Wentworth, who was the father of 13 children, was among the most educated and wealthy men of his town and a significant donor to the construction of the local church. During Congressional debate on the Missouri Compromise two years after Wentworth’s death, New Hampshire Senator David Lawrence Morrill cited him as a model of patriotism and public service, arguing that, “were this worthy citizen alive, he would be forbidden from entering Missouri.”

Angela Matthews has volunteered for  PBHT and BHTNH since the 1990s.  She has served as a tour guide, grant writer, fundraiser, and speaker and was an incorporator of PBHT in the 1990s and in 2016 an incorporator of BHTNH, then serving on the first board of directors. 

This article is part of an ongoing series aimed at highlighting and honoring the stories of notable Black historical figures and families who helped shape New Hampshire and Maine. These stories were originally collected by the Black Heritage Trail of New Hampshire for a project with the Episcopal Church of New Hampshire. Stories are being shared with the partners in The Granite State News Collaborative."