As we celebrate our national independence and look ahead to the 250th anniversary of the American Revolution in 2026, Relearning Highlands History explores a local battle fought by a pioneering regiment of Black soldiers in the Revolutionary War.
In 1781, a groundbreaking Black military unit, the 1st Rhode Island Regiment, took position on the Croton River to hold Loyalist marauders at bay, protect residents, and guard critical lines of communication and transportation. Formerly enslaved by colonists, these soldiers were the first Black Americans to gain their freedom by enlisting to battle the British in the war for independence. And here in the Hudson Highlands, they played a vital and heroic role in the brief but brutal battle of Pines Bridge, according to local historian and author Duane Jackson of Buchanan.
“The 1st Rhode Island’s story is such a unique one in the annals of Revolutionary history,” says Jackson. “And their story touches home, because they fought and served right here.” A U.S. Navy veteran with a lifelong passion for history, Jackson is a member of multiple Hudson Valley historical societies. He helps raise awareness about the 1st Rhode Island by giving talks about their Highlands history and serving as a re-enactor in recreations of Revolutionary War events.
Jackson first learned about the regiment some 20 years ago when visiting a local farm stand. A group of residents gave him a flyer and said they were working to raise funds for a statue honoring the 1st Rhode Island. Jackson was intrigued: “I’d never heard of this Black regiment. I was hooked. I had to know more. That’s when I started doing my research.”
Though Black men fought side by side with colonists when those famed first shots were fired at Lexington and Concord in April 1775, at the beginning of the war they weren’t welcome in the Continental Army. In fact, in November 1775, Gen. George Washington decreed that “neither negroes [sic], boys unable to bear arms, nor old men” could enlist.
“Meanwhile, the British were offering freedom to slaves who joined their ranks,” Jackson notes. Over 20,000 enslaved men and women fled their enslavers in the rebelling colonies to find freedom as Loyalists. Initially, most served as laborers, but as more soldiers were needed, Black Loyalists were allowed to take up arms for the Crown—including Harry Washington, who escaped Mount Vernon while his enslaver was away, leading the Continental Army. Fighting with the Black Loyalists, Harry would rise to the rank of corporal. “So, Washington knew the British were training slaves to be soldiers,” Jackson says. “But what was Washington to do, though? The Southern colonists were completely against having slaves fight on our side.”
By 1778, however, Rhode Island couldn’t recruit enough white men to meet the troop quotas set by the Continental Congress. A general from Rhode Island, James Mitchell Varnum, sent a letter to Washington with a suggestion: Why not enlist enslaved men in the 1st Rhode Island Regiment? Washington passed the idea along to the state’s governor, with no indication if he approved or disapproved. On February 14, 1778, the General Assembly voted to allow the enlistment of “every able-bodied negro, mulatto, or Indian man slave” who chose to do so, and voted that “every slave so enlisting shall, upon his passing muster before Colonel Christopher Greene, be immediately discharged from the service of his master or mistress, and be absolutely free.”
Jackson notes that the Assembly agreed to use money from the public treasury to “compensate slave owners for the loss of their property.” They were also relieved of any responsibility for the health and welfare of enslaved men who enlisted. “The slave owners wanted that in writing,” Jackson says. “No liability!”
Enslaved men did enlist in the 1st Rhode Island, along with free Blacks and Native Americans. The regiment’s numbers eventually totaled 225, and as many as 140 were Black. Many of the white soldiers were laborers and farmhands, Jackson says, and some had worked on the same lands as the formerly enslaved men with whom they now served. White and Black soldiers seem to have gotten along. There are no records of fights or disciplinary problems due to racial integration, writes historian Henry Wiencek: “The objections to the black presence came not from the rank and file, but from the highest levels of policy makers and politician.”
Due to this controversy among policy makers, no more enslaved men were enlisted after June 1778. Months later, in August, the 1st Rhode Island—also called the “Black Regiment”—saw action in the Battle of Rhode Island, repelling three charges by Hessians and fighting the enemy to a stalemate. Maj. Gen. John Sullivan praised the regiment, saying they bore “a proper share of the day’s honors.” Maj. Gen. Marquis de Lafayette proclaimed the battle as “the best-fought action of the war.”
Soon after, the focus of the war shifted south, and the 1st Rhode Island shifted with it. The unit marched into the fort at West Point in January 1781. They then crossed the Hudson River and took position near today’s Croton Reservoir. By mid-May 1781, most of the regiment was camped with the Continental Army near Peekskill, but Col. Christopher Greene commanded a detachment near present-day Yorktown. Greene, a white officer, made his headquarters at Richardson Davenport’s house. About two miles south, Lt. Jeremiah Greenman, also white, commanded a major’s guard of about 50 men at Pines Bridge.
Pines Bridge was one of two bridges crossing the Croton River. The river was an essential source of water for residents and waterpower for grist mills in the towns along its banks. The bridge itself was a critical line of communication. Guards posted there checked travelers for “proper passes to proceed, and received enemy deserters and flags of truce,” according to Norman Desmarais, professor emeritus at Providence College.
That may seem like a fairly tame assignment, but danger was never far away. This part of the Highlands had become a kind of no-man’s-land, according to historian A. J. Williams-Myers, “a desolate, sparsely populated buffer zone” between English forces to the south and the colonists/Americans to the north. The 1st Rhode Island was tasked with protecting local residents from “theft, murder, and destruction” by renegade groups like “De Lancey’s Cowboys,” a marauding Loyalist militia that raided farms and villages in the eastern Highlands, seizing food, weapons, and other supplies
“Those Loyalists, they were saboteurs,” Jackson observes. “They were local, they knew the terrain, and they were constantly gathering intelligence for the British. They spied on the regiment, and they knew exactly when there would be a skeleton crew on duty at Pines Bridge. And they planned a sneak attack.”
At sunrise on Monday, May 14, 1781 Col. James De Lancey led a Loyalist militia of 60 dragoons and 200 infantrymen toward Pines Bridge. They crossed a shallow ford just west of the bridge and marched swiftly up the valley along Turkey Mountain. One party attacked Greene’s headquarters at the Davenport House. A second party struck Greenman’s guard at the bridge.
The fiercest fighting was at the Davenport House, where Greene and his small detachment of soldiers were taken entirely by surprise. “Greene died defending himself, sword in hand, with desperate valor,” Professor Desmarais writes. “Major Ebeneezer Flagg was shot in the head reaching for his pistols at the foot of the bed.”
Delancey’s troops killed eight Black soldiers of the 1st Rhode Island at the Davenport House, troops reported to have “defended their beloved Colonel Greene so well that it was only over their dead bodies that the enemy reached and murdered him,” according to Westchester historian Allison Albee in “The Defenses at Pines Bridge.” Greene and Flagg are buried at the First Presbyterian Church in Yorktown. Nearby is a monument to the 1st Rhode Island Regiment honoring the Black soldiers who died defending them; in 2004, this memorial was added to the African American Heritage Trail of Westchester County.
Duane Jackson recalls that long-ago day at the farm stand, when he met that group of folks looking to raise money for a statue honoring enslaved men who became Black soldiers in the Continental Army, “the day that started me on this historical adventure.” And he remembers the day in 2019, some two decades later, when he stood with many of those same folks at the long-awaited dedication of a statue honoring the 1st Rhode Island Regiment. This battle may be a brief episode in the story of the American Revolution, but to Duane Jackson, it still resonates powerfully today: “Pines Bridge may have been a small skirmish, but to me, it’s part of the very intricate and fascinating history of this pioneering regiment.”