'Wentworth Cheswill’s Ride': Newmarket teacher puts spotlight on life of trailblazer

NEWMARKET — It was during his daily commute to work over a decade ago that John Herman started to become fascinated by the life of Wentworth Cheswill.

“I drove past his historical marker every morning at 6:45 a.m.,” said Herman. “It mentioned that he was a pioneering archaeologist. It made references to different things that he had done that just wowed me – but it’s not sensationalized, it’s a historical marker.”

A remarkable figure in early America, Wentworth Cheswill is known as the first African American elected to public office in the United States. However, his life transcends a single title, serving as a judge, teacher, Revolutionary War soldier and a prominent member of the Newmarket community.

“I started Googling him, and you’re seeing historical blogs that will call him the Black Paul Revere or America’s Black Founding Father, but I was like, why aren’t people using his name?” said Herman. “I believe that people should be using his name, so I then started digging.”

In April, Herman announced the release of a book, which documents the life of Cheswill.

Titled “Wentworth Cheswill’s Ride,” a play off of a famous poem “Paul Revere’s Ride,” the 100-plus page book was released on Cheswill’s birthday, April 11.

'A long time coming': Exeter’s new park to shed light on Black Revolutionary War heroes

How 'Wentworth Cheswill’s Ride' came to print

After a decade of research, compiling facts and debunking myths about Cheswill, Herman initially had another plan to keep Cheswill’s legacy alive.

“I basically collected all these things for his 275th birthday, April 2020,” he said. “I was going to have this year-long thing where I created art, blog prints. I made a comic strip… there were all these kinds of things that I was going to do to educate the public about this interesting guy, and then the pandemic happened.”

Herman’s ideas and his “93 pages of citations and historical notes” came to a halt during the pandemic, and he was “devastated.”

“I can’t write a history book that anyone’s going to read,” he said. “I’m not a historian, I’m an English teacher.”

It wasn’t until a friend gave Herman a book – Bill Bryson’s “Shakespeare” – which Herman regarded as “a short, biographical book that is kind of funny but also deeply serious, well researched and thoughtful.”

Herman said it introduced him to a different kind of writing.

“A friend just passed that to me and said, ‘You should write a book like this – something small, something personal that shows your passion and see what happens,’” he recalled. “I had been feeling guilty because I had pieced together (Cheswill’s) life. I had 93 pages of notes that were going to die in a Google Doc. I started feeling almost an imaginary pressure that I should do something with all these materials, or else he would continue to be forgotten for another 100 years. So, I started writing during the pandemic.”

More: SOS Recovery closing Hampton location, relocating to Exeter

Wentworth Cheswill: Forgotten no more

“Wentworth Cheswill’s Ride” is split into three sections – the life of Cheswill’s grandfather, father and then himself. It was something that Herman felt strongly about sharing, he said.

The book begins with the life of Cheswill’s grandfather, who was enslaved in Exeter. It then moves onto the life of Cheswill’s father, Hopestill, whose carpentry work includes framing the John Paul Jones house and Strawbery Banke’s Stoodley’s Tavern in Portsmouth.

Hermann said Hopestill would use his skills to build houses for captains and merchants and then “used all that wealth to invest in his son and give him the opportunities that his enslaved father never had.”

“I almost saw three generations of a family transform from enslavement to helping craft the birth of the nation,” said Herman.

Some of the fun facts that Herman found while writing this book include that Cheswill was part of the first 28 kids to attend the Dummer Academy (now known as the Governor’s Academy), an institution that “cranked out some of the most prominent individuals in early America.”

“(Cheswill) roomed with – just to show you with the type of people that went – a young Sam Phillips, the kid who grew up to open Phillips Andover Academy and whose benefactor who sent him there opened Phillips Exeter Academy,” he added.

Following his education at the Dummer Academy, Herman said Cheswill returned to Newmarket and became the first teacher with his own schoolhouse in the community and was regarded as the first African American judge.

Cheswill also served as Newmarket’s town messenger, tasked with the urgent relay of intelligence to Exeter’s patriot leaders for the Committee of Safety during the Revolutionary War. He also fought in the American Revolution's first major victory in the Battle of Saratoga under John Langdon.

"When George Washington came to New Hampshire, he visited John Langdon. John Langdon had a hand in helping Ona Judge escape," said Herman. "Wentworth Cheswill was involved with all these people, yet forgotten."

Hermon said Cheswill was also "prolific" as a public servant, serving in town offices throughout his entire life.

"From what I can gather, he served every year for 50 years except one," said Herman. "That one year that he didn't serve in any office is the year that the Constitutional Convention was happening. John Langdon went down and signed the Constitution for New Hampshire, and there were rumors that (Cheswill) wasn't around that year because he was part of John Langdon's entourage and went down and influenced the creation of the Constitution."

Legacy cemented: Exeter Fire Chief Eric Wilking retires after 42 years

On a mission to keep Cheswill’s memory alive

Herman said when he read Cheswill’s historical marker over a decade ago, he was instantly inspired. He said he wishes to do the same for other members of the community by keeping Cheswill’s memory alive with his book.

“He was a historian, a teacher and was prolifically involved in his community, it seems like someone we should look up to,” said Herman. “If we did have a new type of folk hero, it would be someone who inspired us, who cares more about the community and to be involved and to be passionate about what came before us. … I think we’ve put a lot of people on pedestals that maybe we shouldn’t. I didn’t consider him lightly, I really am inspired.”

Following the book release, Herman said there are still new facts and stories about Cheswill that are coming to light, which might make for a second book. In the meantime, Herman is also behind the effort to remember “Newmarket’s Town Father” and build a life-size statue of Cheswill, which he hopes to unveil on the town's 300th birthday in 2027.

This article originally appeared on Portsmouth Herald: 'Wentworth Cheswill’s Ride': Newmarket teacher chronicles trailblazer