The death of Col. Christopher Greene of the Rhode Island Regiment during the Loyalist raid at Pine’s Bridge on the Croton River in May 1781 represents one of the most brutal and dramatic episodes of irregular warfare in the American Revolution. Drawing upon contemporary correspondence, eyewitness testimony, military reports, and later historical compilations, this surprise attack led by Loyalist commander Col. James De Lancey can be reconstructed. Situating within the violent context of Westchester County’s “Neutral Ground,” the episode reveals the critical role of intelligence networks, local informants, and mounted Loyalist raiders in shaping military operations during the final years of the war. Greene’s death illustrates both the vulnerability of advanced Continental outposts and the brutal character of frontier warfare along the Hudson River corridor.
(Artist unknown, eighteenth century portrait. Public domain)
By the spring of 1781 the American Revolution had entered its seventh year, during most of which the region immediately north of British-occupied New York City was one of the most volatile theaters of the war. Westchester County, lying between the British garrison in New York City and the American defenses in the Hudson Highlands, had become widely known as the “Neutral Ground.” The phrase suggested a buffer zone between opposing armies, but the reality was far different. It functioned as a violent frontier where Loyalist raiders, Patriot militia, and Continental detachments fought a constant shadow war of raids, ambushes, intelligence gathering, and retaliatory violence.
The Neutral Ground was defined less by formal battle lines than by mobility and information. Mounted Loyalist units operated from British-controlled territory around New York City, striking suddenly at isolated American posts, farms, or supply routes before retreating to safety. American forces attempted to counter these raids by establishing a chain of advanced outposts designed to monitor key roads and river crossings. These posts served as an early warning system protecting the Hudson River corridor and the vital fortifications at West Point, the strategic centerpiece of American defense in the region.
One of the most important natural barriers in this defensive system was the Croton River, which flows westward into the Hudson approximately thirty miles north of Manhattan. Several bridges crossed the river, including Pine’s Bridge, which connected the interior settlements of Westchester County to the Hudson Valley and the American lines in the Highlands. Control of these crossings was essential, for a successful Loyalist raid across the Croton could penetrate deep into Patriot territory before the Continental Army had time to respond.
To guard these crossings the Continental Army stationed small detachments along the river. Such posts were strategically necessary but inherently vulnerable. Isolated from the main army and often composed of only a few hundred men, they could easily be overwhelmed if surprised by a larger raiding force.
In early May 1781 Col. Christopher Greene of the Rhode Island Regiment commanded one such advanced post guarding the Croton River near Pine’s Bridge. Greene was a veteran officer whose reputation had been firmly established earlier in the war. In October 1777 he commanded the American garrison at Fort Mercer during the Battle of Red Bank, where his small force successfully repelled a powerful Hessian assault led by Count Carl Emil Kurt von Donop. The victory brought Greene considerable recognition throughout the Continental Army.
By 1781 Greene commanded the Rhode Island Regiment, one of the most experienced units in the Continental Army. The regiment consisted largely of seasoned soldiers who had served through years of campaigning and hardship. Its officers were well acquainted with the dangers of frontier warfare.
Greene established his headquarters at the house of Richardson Davenport near Pine’s Bridge. Several officers were quartered there, including Maj. Ebenezer Flagg, while detachments guarded the nearby crossings of the Croton River.
Lt. Col. Jeremiah Olney, who later succeeded Greene in command of the regiment, described the disposition of the American outposts:
The advance guard of the American army were on Croton river, which falls into the Hudson about 30 miles above New York; over this were two bridges at several miles distant from each other; near that on the main road was stationed the principal part of the guard, consisting on the whole of a Major’s command; a Captain’s command being detached some miles on the right and left. Small parties patrolled below the bridges.[1]
Despite the apparent security of the position, the American officers believed the Croton River could only be crossed at the bridges. Olney later admitted the river “was not supposed to be fordable,” a mistaken assumption that would prove fatal.
Across the American lines Loyalist forces commanded by Col. James De Lancey operated from Morrisania near British-occupied New York City. De Lancey commanded a regiment of Loyalist cavalry and refugees who frequently conducted raids into Patriot territory. These troops were highly mobile and intimately familiar with the terrain of Westchester County.
Intelligence concerning Greene’s outpost was supplied by a Loyalist named Gilbert Totten. Several witnesses later recalled that Totten had previously been insulted by American troops and vowed revenge. One account remembered him declaring that the next flag sent to the American lines would be “a bloody one.”[2] Another witness recalled that when Totten was insulted at Pine’s Bridge, just before the capture of Davenport’s house, he said on parting to the officer who commanded the guard, “When I come up again it will be with a red flag,” implying violence, and that Black soldiers stationed at the American post would soon disappear.[3] These recollections illustrate the intensely personal animosities that fueled violence in the Neutral Ground.
During the night of May 12–13, 1781, De Lancey assembled a raiding force and marched north toward the Croton River. A contemporary Loyalist newspaper reported the strength of the expedition:
The party who made the attack marched from Morrisania under the command of Col. De Lancey, and consisted of about one hundred cavalry and two hundred infantry.[4]
The Loyalists crossed the Croton River at a ford and divided their force. One detachment moved toward Pine’s Bridge while the other advanced directly toward Davenport’s house. Because the Americans believed the river could only be crossed at the bridge, they were completely unprepared for such an approach.
The attack occurred shortly before dawn on May 13, 1781. Inside Davenport’s house the officers were asleep when the alarm was raised. According to Lieutenant Colonel Olney, the officers sprang from their beds as firing erupted outside. Major Flagg was near a window when a musket ball fired from outside struck him in the head. Olney later described the moment:
The ball passing through his head, he fell forward upon the bed and there continued. The enemy breaking into the room found him in that situation and thinking him to be sullen gave him several cuts in the back with their broad-swords.[5]
Flagg died almost instantly.
Colonel Greene attempted to rally the defenders as the Loyalists burst into the house. Lydia Vail, granddaughter of Richardson Davenport, later recalled Greene shouting to the soldiers below, “Stand to your arms men! Courage! They are only a parcel of cow boys, fire away!”[6] Despite Greene’s efforts the Loyalists quickly overwhelmed the defenders.
Several sources indicate that Greene fought fiercely once the attackers burst into the room. According to one account, the first Loyalist entering the house was seized by Greene himself. Joshua Putney described the moment:
When Davenport’s house was taken one Ackerly broke in and entered first; Col. Greene seized and threw him down, and was on the point of dispatching him with his sword, when he received a cut in his arm, which disabled him.[7]
Henry Lee later described Greene continuing to resist even after receiving serious wounds, writing that he “singly received them with his drawn sword” until he was overwhelmed.[8]
The most detailed description of Greene’s injuries appears in a letter written the day after the attack by Capt. Thomas Hughes, paymaster of the Rhode Island Regiment. Writing to Greene’s son, Hughes described the wounds inflicted during the assault:
his right wrist almost cut off in two places, his left in one, a severe cut in the left shoulder, a sword run through his body, a bayonett into his right side, another through his body, his head cut to pieces in several places, his back and body cut and hacked in such a manner as gives me pain to inform you.[9]
Despite these terrible injuries Greene remained alive. Hughes wrote that the Loyalists carried him away during their retreat and that he was “carried about three-quarters of a mile from his quarters, where they left him to dye . . . through the loss of blood and not strength to go forward, finished his days in the woods.”[10]
Lydia Vail later recalled that Greene was forced onto a horse as the Loyalists withdrew. As they approached the road near Pine’s Bridge he collapsed from the loss of blood:
Green held on the horse till they were just coming out of the wood into the main road. He then fell off, and they found he had fainted and was dying from loss of blood. They then laid him on the bank by the side of the road, and passed on.[11]
According to Vail’s testimony, Greene was left lying beside the road among whortleberry bushes. When he was later discovered he had been stripped of most of his clothing and was wearing only his shirt and drawers.[12]
Gen. George Washington confirmed the sequence of events in a letter to the President of Congress written on May 17:
Colonel Greene, who commanded our party, was mortally wounded in his quarters. . . . The enemy attempted to carry him off, but he died upon the road.[13]
The following day Greene’s body was recovered and brought back to the American lines. He and Major Flagg were buried with military honors in the churchyard at Crompond. Lydia Vail described the funeral:
The widow of Col. Greene was present at this ceremony, which was conducted with great pomp; a large number of the military, as well as of citizens, moving in the procession, while the bands played the most solemn airs from the dead march.[14]
Col. Christopher Greene was forty-four years old when he died. His widow Anne Lippitt Greene and their children survived him in Warwick, Rhode Island.
The destruction of Greene’s outpost illustrated the dangers facing advanced Continental positions in the Neutral Ground. Loyalist raiders had demonstrated that even experienced troops could be overwhelmed through intelligence, mobility, and surprise.
Although the loss of Greene and several officers was deeply felt, the broader strategic situation remained unchanged. Washington’s defensive line along the Hudson remained intact, and the British never succeeded in breaking through the American positions guarding West Point. Yet the events at Pine’s Bridge revealed the brutal realities of irregular warfare during the Revolution. In the contested frontier of Westchester County, the war was fought not only by armies maneuvering across battlefields but also by raiding parties, scouts, and local inhabitants whose loyalties and grievances shaped the violence of the Neutral Ground.
[1] Jeremiah Olney letter describing the Croton River outposts, quoted in Robert Bolton Jr., A History of the County of Westchester, from Its First Settlement to the Present Time, vol. 1 (New York: Alexander S. Gould, 1848), 265–266.
[2] Nathaniel Montross testimony regarding Gilbert Totten, Macdonald Manuscripts, quoted in Bolton, A History of the County of Westchester, 263.
[3] Abraham Weeks testimony, Macdonald Manuscripts, cited in Bolton, A History of the County of Westchester, 263–264.
[4] “Account of the Surprise at Croton River,” Rivington’s Royal Gazette (New York), May 16, 1781.
[5] Bolton, A History of the County of Westchester, 266.
[6] Testimony of Lydia Vail, October 19, 1844, recorded in Bolton, A History of the County of Westchester, 267.
[7] Testimony of Joshua Putney, Macdonald Manuscripts, quoted in Bolton, A History of the County of Westchester, 264.
[8] Henry Lee, Memoirs of the War in the Southern Department of the United States, vol. 1 (Philadelphia: Bradford and Inskeep, 1812), 297–298.
[9] Thomas Hughes to Job Greene, May 14, 1781, in Bolton, A History of the County of Westchester, 270–271.
[10] Ibid.
[11] Ibid.
[12] Ibid.
[13] George Washington to the President of Congress, May 17, 1781, in John C. Fitzpatrick, ed., The Writings of George Washington, vol. 22 (Washington, DC: U.S. Government Printing Office, 1937), 150–151.
[14] Testimony of Lydia Vail, recorded in Bolton, A History of the County of Westchester, 269.
One thought on “The Death of Colonel Christopher Greene at Pine’s Bridge, May 1781”
Dear Mr. Bruckshaw,
The subject of the Pine’s Bridge Massacre has fascinated me since boyhood because I grew up a short distance from the event at a place called Croton Heights in Yorktown Heights, NY,
Your article captures the extent of the animosity that evolved between the Loyalists and Patriots, in my opinion. It is also my opinion that the willingness of DeLancey’s Refugees to give no quarter is indicative of a greater level of anger that may be based on the use of “colored” and non-local troops by the Continental Army while there were plenty of local Continentals at the Peekskill encampment.
And, based on the McDonald Papers’ and historian Mr. Allison Albee’s field maps, it is beyond my comprehension how Col. Greene’s troopers were unaware of the several fords across the Croton both east and west of Pine’s Bridge.
If your readers should wish to dig further into this subject, I recommend the 12-part series called “Defense of Pine’s Bridge” by Mr. Alison Albee [Pres. and Co-Editor of the Westchester County Historical Society and its quarterly publication, The Westchester Historian, in the late ’50s & ’60s] which can be read in the magazine’s Vol. 34-#3 through Vol. 37-#2 digital archives at https://westchesterhistory.com/quarterly-journal/ .
Again, your article was enjoyable to me.