Cheswill’s Ride

Wentworth Cheswill’s Ride 

by John Christian Herman

Read these words for I shall tell

Of a man whose name should ring every bell,

For his story is revolutionary,

driven by a love for community and liberty. 

Behold the life of Wentworth Cheswill. 


His story begins before America was born,

Before cars, computers, and football scores,

A simpler time, but, as you shall see,

A time full of wonder and opportunity.


Before he was born, or his father before him, 

His grandfather was stolen from his African homeland.

Brought to a strange land, given a new name — and enslaved, 

Richard worked until his freedom was gained.

Despite the trials and hardships he underwent, 

He became New Hampshire’s first landowner of African descent.


Richard’s son, Hopestill, was a housewright by trade.

That means he built houses; some stand to this day.

He built the John Paul Jones House, beautiful and hardy,

But he could never enjoy a housewarming party

Unless granted permission by the homeowner’s hand 

For his appearance was not that of a common free man.


In 1746, on an April morn’ –in Newmarket, 

Hopestill’s son, Wentworth Cheswill, was born.

Known for the trade of sugar and slaves,

Newmarket’s new path would be paved.

Hopestill worked with hammer in hand

To send his son to the best school in the land.


Enrolled in the newly opened Governor’s Academy,

Wentworth studied Latin, Greek, and geometry. 

He fostered a passion for writing and reading, 

Graduated, and returned home to begin teaching. 


A year after marrying Mary Davis of Durham, 

Wentworth was town constable, an elected position.

Not only did Newmarket vote in a great man. 

‘Twas the first elected office held by an African American. 


At no time did Wentworth’s public service decrease.

He even served 12 years as a Justice of the Peace. 

By old age, he was selectman, moderator, auditor, 

Constable, assessor, and even the coroner. 

To think, a slave’s grandson was a judge in 1769,

Seven years before the Declaration of Independence was signed! 


I know in the books you have read, 

Wentworth is not mentioned, just others instead.

But what sets him apart is a tale full of glory. 

History, as remembered, never tells the whole story.

Heroes can be forgotten. Past deeds become blurry.

But now it all changes. You shall learn he is worthy!


As colonial tensions grew against British rule,

Wentworth wished to protect more than his school.

He took an oath to protect his community bravely

As a messenger (like Paul Revere) for the Committee of Safety.


Next Wentworth signed an oath at risk of fortune

To take up arms against the British sovereign.  

The Association Test of 1776 gave the Founding Fathers confidence

To sign, without hesitation, the Declaration of Independence!


Wentworth enlisted in the Continental Army,

As a member of John Langdon’s Light Horse Volunteer Company,

He charged to New York, a 250-mile journey,

And fought in the Battle of Saratoga, America’s first victory.


When Wentworth returned home from the war, 

his love for community only soared.

Not satisfied with being just a teacher anymore, 

he served on his hometown’s inaugural school board.


Meanwhile his passion for archaeological inquiry 

Inspired Jeremy Belknap’s first volumes of history, 

His notes and artifacts, too many to list,

Earn Wentworth the title of New Hampshire’s first archaeologist. 


Can you believe there is more? That isn’t the end! 

How far did Wentworth’s influence extend? 

When Oney Judge, personal slave of Martha Washington,

Escaped to the harbor town Wentworth defended,

His commanding officer at Saratoga, now a senator, hid her. 

Instead of honoring George Washington’s request to return her.


Defying the first president in the name of liberty

Could go down in history as the greatest of ironies. 

But who inspired him to act with such valor?

Was it one who once fought beside him –a friend, patriot, and scholar–

Who taught Senator Langdon that liberty was not bound by skin color?


Regardless, Wentworth always lived by deeds honorary.

In 1801, he led the creation of Newmarket’s first library.

He continued to serve to the end of his time,

Even his end was more adventurous than sublime.

In 1816, there was a year without a summer –a cataclysmic wonder 

Caused by a volcano that brought dark clouds and thunder.


Across the Earth, frosts struck even August and July.

Across the ocean that year’s weather inspired the writing of Frankenstein

With crops ruined, those close to birth or death did not survive.

Following these circumstances, Wentworth Cheswill died.

He passed in the Spring at the age of seventy-one.

Visitors can still view his resting place in the community that he loved.


In the hour of darkness and peril and need, 

We call upon Wentworth Cheswill to inspire a creed

To live as he lived by community and care,

In a world of colonial strife and despair,

An astonishing life beyond all compare.  

Let us tell his tale by song, painting, and pen. 

So that we never forget Wentworth Cheswill again.



John Langdon who commanded Wentworth Cheswill and the Light Horse Volunteers during the Battle of Saratoga went on to be a delegate to the Constitutional Convention, signed the United States Constitution, and was a governor of New Hampshire.

At the end of his life, President George Washington, who had owned slaves since he was eleven years old, freed them in his will, but those freed did not include the slaves of his wife, Martha. After Martha’s death, Oney “Ona” Judge’s ownership was passed to a cousin. Ona lived forever in fear of being recaptured and enslaved.

As for Wentworth Cheswill, despite his continued contributions to his community and nation, he was mostly forgotten, only to be referenced briefly during debate over the Missouri Compromise, a statute designed to limit the spread of slavery. In an address opposing the prevention of people of mixed race from attaining Missouri citizenship, Senator David Morril stated that, “In New Hampshire there was a man by the name of Cheswill, who, with his family, were respectable in point of abilities, property and character. He held some of the first offices in the town in which he resided, was appointed a justice of the peace for the county, and was perfectly competent to perform with ability all the duties of his various offices in the most prompt, accurate and acceptable manner. But this family are forbidden to enter and live in Missouri.”