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The Cowboys of the Ramapos

The Legend of Claudius Smith

The following essay was written in 1969 by Dr. Charles A. Huguenin, an adjunct professor of English at Pace College.  It is perhaps one of the best accounts of the escapades of the outlaw Claudius Smith that we are aware of.  It was originally published in Pace College’s quarterly; vol. 20, No. 3, summer 1969, and is reprinted here, with permission of Pace College.
(The following version has been edited and modernized.)

by Charles A. Huguenin

Under the leadership of the notorious Claudius Smith, a gang of marauders known as the Cowboys of the Ramapos operated in lower New York State during the Revolution.

During the early part of the Revolutionary war (1775-1783), with the county of Westchester on the east side of the Hudson River and Orange County on the western side, which then included Rockland County, there was comprised a somewhat neutral ground.  This area lay between the British army who were quartered in New York City, and Washington's Continentals who were spread out along the Hudson River between Fort Montgomery and Newburgh.   This so called neutral ground, however, was infested with lawless bands of marauders, called “Cowboys” and others known as “Skinners.”  The Cowboys were largely refugees, belonging to the British side engaged in plundering nearby inhabitants of their cattle and valuables. The Skinners generally professed attachment to the American cause and lived chiefly within the Patriots lines.  More unprincipled than the cowboys, they committed depredations indiscriminately upon friends and foes alike.


Those residing within neutral ground endured much suffering during the war, for they were sure to be abused and plundered by one party or the other. If you were to take the oath of fidelity to the American cause, the Cowboys were sure to plunder you; and if you did not, then the treacherous and rapacious Skinners would denounce you as a Tory, loyal to the British cause, and seize your property confiscating it in the name of the state. The execution of law was assumed by outlaws, and partisans on both sides in the intercontinental struggle were reduced to common ruin.

Lines between the two factions of marauders were not rigid. One day they would be engaged in a broil; the next day they would be in league with each other in plundering their own friends as well as their enemies. Both parties were enemies to any farmer or lonely traveler whose unprotected situation offered a prospect of booty.

On the east side of the Hudson River, the neutral ground extended for about 30 miles, with Tarrytown as the theater of stormy scenes between the supporters of the British Crown and those of the American Congress.  

On Watermelon Hill, about a mile and a half southeast of Lake Mahopac, Cowboys built pens to shelter stolen horses until they could drive the animals in safety to New York City for use in the British Army.

On the west side of the Hudson River, plunder, outrage, inhuman barbarity, and even murder ran rife in the dubious neutral ground that covered an area more than 55 miles in extent.  Historian Joshua Hett Smith, who lived in Haverstraw, has left a contemporary account of the plight of its terrified inhabitants of that area:

“No one slept safely in his bed. Many families hid themselves at night in barns, wheat-ricks, corn-cribs, and stacks of hay; and on each returning day, blessed their good fortune that their houses had escaped the flames. The composition of these predatory gangs of Cowboys was loose, including confirmed Tories, British deserters, runaway slaves, and Indians; their number was indeterminate; and their tastes in thievery were undiscriminating. Despite the name by which they were known, they did not confine their attentions to driving off the live stock from the farms of their unfortunate victims. Anything portable and marketable with the British in New York City fell within the scope of their acquisitive proclivity, and their booty comprised not only money and silver plate but also saddles and articles of clothing. An itemized list of articles stolen from a resident of Wallkill included shirts, jackets, sheets, pillow cases, .and handkerchiefs, besides silver plate and money.

From every period of havoc in the onward march of civilization emerge names of individuals whom history has endowed with the responsibility of leadership.  In this period, tradition has settled upon the loyalist Claudius Smith as the leader of a gang of these Cowboys.  It has further imbued him with daring and wickedness.  The host of Claudius Smith’s booty, it is alleged, consisted of horses and cattle, for which he found a ready market among the British in British-held New York City.  This earned him the nick name from those benefiting from his operations “The Cowboy of the Ramapos.”

Claudius Smith’s so called headquarters of operation were located in Smith's Clove (now Monroe) and in lairs in the Ramapo Mountains.  Two caves, located about a mile east of the railroad station in Tuxedo, are known  locally today as the “Claudius Smith Caves.”  They are not cavernous caves as one might expect, but rather a pair of long, horizontal rock shelters at the foot of successive cliffs. The upper of this pair, allegedly the den of this notorious Cowboy, is some 8 to 10 feet high, 30 feet long, and 10 feet deep. In Revolutionary times his gang, it is said, improved upon the natural shelter of the cliffs by rolling huge boulders in front its entrance, protecting it from winds and storms.  It can be noted that this was done at great labor to the members of the gang.  The boulders have long since fallen from their original positions, but they can be seen today scattered around the vicinity of the cave.

The lower cave, which is longer and deeper but not so high, served as a rude stable to shelter the horses of the opportunists and the stolen livestock that they had garnered in their marauding expeditions through the Ramapos.  Both caves, removed from each other by about 150 yards of rough terrain, were large enough to accommodate a considerable number of men, horses, and cattle. A spring that ran along the mountainside between the caves furnished a convenient source of water for both Cowboys and beasts.

An inland promontory, offering one of the most spectacular views to be found in the Ramapos, lies in the mountains only a short distance from the pair of caves. Today’s sightseer may appreciate the strategic value of such a location to Claudius Smith and his followers.  The main road in Revolutionary times wound for 16 miles through the valley below. Traffic along this highway could be detained at pistol point and looted within a short distance of the lairs. The robbers could find security in their customary hide-out, in the shaded glens, or in some fault in which the region abounds.

The wild, Tory-infested "Clove,” which was chiefly the Ramapo Valley, extended northward to Smith's Clove (now Monroe), which was named after Claudius Smith's father. “This district was celebrated for the attachment of the inhabitants in general to the British interest,” wrote Joshua Hett Smith. "Almost all communications between Canada and New York passed through this place, there being a regular connection of the King's friends, where they could take their stages during the whole war, in the greatest safety.” “Through this clove, by way of Ramapo,” maintained historian Benson J. Lossing, “was the best route for an army from New Windsor (near Newburgh) into the upper part of New Jersey.”

Over it moved George Washington’s army northward from Middlebrook, New Jersey, to encamp in July 1777, eleven miles above the Ramapo Pass. The region was so overrun with Cowboys and other Tories that Washington could not get reliable accounts of British General Howe’s proposed operations.

The following incident will give some indication of the serious ways in which the Cowboys interfered with Washington's conduct of his campaign against the British-

While the Colonial troops were encamped at Montgomery, a soldier by the name of John McLean was selected to carry a message to Newburgh, where Washington was stationed.  In a lonely place where Stony Brook crossed the Shawangunk Road, a number of men leaped from ambush, seized him, gagged him, robbed him of his dispatch, and tied him to a tree. There they left him. Night came on, and with it an ominous and bone chilling coldness. McLean wriggled throughout the night within his bonds to maintain circulation in his numb body. He prayed fervently that some chance passerby would see him in that deserted spot and save him from death by freezing. Not until morning did a lone traveler come upon the helpless captive. Through frost-bitten lids McLean watched the man approach, stare, and finally rush to release him from his gags and bonds. Mclean suspected that the men who had attacked him were members of the gang of Claudius Smith. It is not improbable. Claudius Smith’s interest in the property of others did not exclude dispatches carried on the persona of victims he waylaid. Mrs. Ashman's grandfather, who lived near Blooming Grove, was captured by the cowboys and was threatened with a dunking in a deep well unless he delivered over the important papers he carried.

Although the active and influential Whigs (supporters of the American cause) were the special objects of Smith's hatred and vengeance, his pro-British sympathies prompted him at least on one occasion to make an attempt to acquire property belonging to the Continental Army. He and a trusted follower named John Brown broke into an enclosure near the American lines and proceeded to drive off a number of oxen. However, what they didn’t anticipate apparently was the plodding pace of their apprehended booty.  Before the pair could reach a retreat, the two were seized and jailed in Kingston.

The Council of Safety, July 18, 1777, ordered that “Sheriff Dumont cause to be removed from the jail in Kingston to the jail in Orange County, Claudius Smith and John Brown charged with stealing oxen belonging to the Continent.”

After the transfer had been effected, one of Claudius Smith's cronies carried the news of his confinement to scattered contingents of his band in their different places of rendezvous. A number of his followers converged upon Goshen and seized the sheriff, who had custody of their leader. They placed a rope around his neck and issued a threat that was not at all unclear to the sheriff. He discreetly surrendered Smith and Brown to their comrades.  They left Goshen in triumph assuring that their lucrative ventures could continue in the future.

Only a very few of the marauding exploits of Claudius Smith and his band have been preserved. One of them deals with a beautiful mare, owned by Colonel Jesse Woodhull.  Woodhull was a brother-in-law of Fletcher Matthews, one of Claudius Smith’s trusted followers, and a second cousin of Austin Smith, another member of Smith's Cowboys.  After Claudius Smith's acquisitive admiration of the mare became known to the colonel, he quickly transferred the horse from his barn to his cellar, which served as her stall for a number of weeks.

In broad daylight Claudius Smith quietly slipped into the colonel's house while the family was upstairs at tea, led forth the horse, leaped upon her back, and galloped off.   The first indication that the members of the household  had of the theft, was a yell of defiance from the Cowboy as he was riding off on his stolen prize.  A guest of Woodhull’s sprung up from the table, seized a gun, and leveled it at the outlaw through the window.  As he was about to squeeze the trigger on the receding target, Woodhull knocked the poised rifle aside.  The colonel cautioned, “If you shoot and miss him, he will kill me.”

The theft of his favorite mare was base repayment for the colonel's befriending members of Claudius Smith's own gang.  Loyal ties among friends during the Revolution, however, were repeatedly broken, and even loyalties among family members were put on hold. “All friendly [associations were] at an end,” observed historian Joshua Hett Smith, in a district where “literally, brother was against brother, and father against son, frequently imbruing their hands in each other's blood.”  At the same time that an intercontinental war was being waged with England, a civil war disturbed every home.  One of Claudius own brothers, David, was a patriot in the Second Regiment of the Orange County Militia- another brother, Julius, had gone to New Brunswick to fight on the side of the Crown. Claudius himself had four sons, three of which had adopted the politics of their Tory father and rode with him on many of his nefarious exploits.  Samuel, the eldest of his sons, had defied the Tory politics and cast his lot with the patriots in Colonel William Allison's Fourth Regiment of Orange County Militia.

Whether Claudius Smith ever committed murder in cold blood will always remain an unresolved question, but on the morning of October 7, 1778, Major Nathaniel Strong was lying dead.  According to the testimony of thirteen citizens of Orange County, “a company of armed men one of them supposed to be Claudius Smith,” had broken into Major Strong's house between one and two o'clock in the morning, and “three men fired at him.”  The deceased major's wife swore in a deposition that when the party of marauders had attacked the house, "she heared hur husband say” that it was Claudius Smith.  

The Cowboy has never tried for murder, but tradition has accorded him credit with the capacity of murder.  Charles E. Stickney, author of the History of the Minisink Region, contended that Claudius Smith kept inhabitants of Orange County from sleeping peacefully in their beds for fear of "getting their throats cut before morning.”

Because the slaying of Major Strong was leveled upon Claudius Smith, justly or otherwise, the events of the night of October 6, 1778, take on a context of paramount importance.

It was a night rich in prospective designs. If it were a typical one, Smith must have led an exceedingly active nocturnal existence. The gang’s first stratagem involved the looting of the house of Captain Woodhull in Oxford and the capture of its owner “ded or a live.” The object of the larceny was a set of silver. When Claudius with four of his party, some of whom were his sons, sought admittance to the home about twelve o'clock at night, the captain was absent on duty in Clarkstown.  After his wife had refused to unfasten the 1atch, the gang proceeded to break down the door.  Mrs. Woodhull surmised their identity and their intent and while the desperadoes were still busy at the resistant door, she hastily gathered valuable articles together and hid them in her child's cradle.  On top of then she deposited the child.

The rogues finally burst into the room and conducted a search of the house.  Mrs. Woodhull, meanwhile, pretended to be very busy beside the cradle, trying to quiet little Fanny.  The artifice succeeded.  The frustrated felons finally left the house with several valuable articles, but short by a wide margin of the spoils they had anticipated in garnering.  Before galloping away, the desperadoes spied in a meadow near the house the horse belonging to Luther Conklin, a relative of the Woodhull’s who was also absent from the house of his host at the time of the robbery.  The acquisition of the horse by the band was an elementary procedure. 

From Oxford the felons rode to Blooming Grove to pay a call in their inimitable lawless fashion on Major Nathaniel Strong. The purpose of this second project was also murder.  With better luck then their last assault, they found that the major was within, but because the gang did not reach the house until about 1 AM, the prospective victim was asleep in an inner room.  The customary method of gaining admittance by breaking down the door aroused the major who then promptly armed himself with a pair of pistols and a musket.  After the desperados had demolished the outer door, they rushed into the first room and proceeded to break through one of the panels of the door to the inner room. Dismay overcame them when they saw through the smashed panel that their intended victim was armed to the teeth.  The predicament called for the exercise of either courage or cunning and the situation seemed to evoke no courage. Taking shelter behind the walls of the room, the assailants promised the major they would not harm him if he should surrender his arms. Vastly outnumbered, the trusting major set his musket against the wall. 

As he approached the door to open it, the outlaws shot at him through the shattered panel.  Their fire had no chance to miss at such a close range.  The major sank to the floor and died without uttering a word.  Appropriating two bridles and a saddle, the gang cantered off to its old haunts.

If Claudius Smith earned his reputation for courage, shrewdness, and marksmanship through such conduct, then it should be noted that the legend has been grossly misleading in the conferment of its honors.  The murder of  Major Strong evoked a storm of protest.  An account of this fresh instance of villainy along with a plea for the capture of the gang was dispatched to Governor Clinton.  The governor acknowledged the request with a proclamation offering a reward of $1,200 for the apprehension of Claudius Smith and $600 for that of his sons, Richard and James.

With a price on his head, Claudius Smith fled from his old haunts in the Clove with British-held  New York City his immediate destination.  His object now was to find a place that offered security from harassment by the law and longevity for his misguided life.  Probably under the impression that the eastern reaches of Long Island would be more advantageous because of their remoteness, he moved thence to take up lodgings with a widow near Smithtown. His luck was running out fast and fate accorded him fewer than two weeks of freedom.

After the British had taken possession of Long Island, a number of Whigs had moved with their families across Long Island Sound into the more congenial atmosphere of Connecticut.  Among these was Major Jesse Brush, a stout anti-Tory farmer, who left his property in Long Island in the care of tenants.  The major made occasional clandestine visits back there though to personally look after things. On one of these visits he accidentally learned about Claudius Smith's residence in the neighborhood of Smithtown.

Returning to Connecticut, he imparted his discovery to an acquaintance, Mr. Titus, also a native Long Islander and a man possessed of unusual enterprise and resolution. Titus agreed to join Major Brush in a daring plan to capture the outlaw for the attractive bounty.

They engaged three other men to assist them, armed themselves muskets and pistols, and prepared a whale boat to transport them to Long Island. One November night, under cover of darkness, they crossed Long Island Sound. Reaching the Long Island shore about eleven o'clock, they guided the boat into a small bay north of Smithtown.  Leaving one of their number in charge of the boat, they proceeded about a mile southward across the island to the retreat of the Cowboy.  When they reached the house, they entered without knocking for fear of alerting Smith and found his landlady seated by the fire.  Major Brush, who was apparently acquainted with the woman, asked her if Claudius Smith were in the house.

She replied, “He is in bed. I will go and call him.” Instantly Major Brush retorted, “No, tell me where he lodges.”
“Upstairs in the bedroom,” replied the puzzled woman.
The major warned the landlady to be quiet.  He promptly took a candle, and leaving one of his companions below, he with the other two crept cautiously up the stairs.  As soon as the three intruders entered the room they seized the sleeping outlaw.  Smith awoke with a start and made violent resistance and a futile attempt to grab his pistols concealed under his pillow.  The major and his posse lost no time in binding Smith’s arms with a cord. They then marched him bound, and covered with their firearms, to the waiting whaling boat.  Without incident they re-crossed Long Island Sound and the next morning landed on the Connecticut shore. The captors placed Smith in irons and a guard over him.

Major Brush forthwith sent word to Governor Clinton in Poughkeepsie that he had Claudius Smith in his custody.  Clinton authorized him to conduct the Cowboy through the southern part of Connecticut to Fishkill Landing and to turn him over to a party of guards, including Colonel Isaac Nicoll, Sheriff of Orange County.  On the twentieth of the month, the accounts of Governor Clinton show an entry for 480 pounds, charged to “cash paid Major Jesse Brush for apprehending & securing the body of Claudius Smith.”

Claudius Smith was apparently led, not directly to Fishkill Landing, but to Poughkeepsie after his capture. It may have been some time before he was eventually turned over to Sheriff  Nicoll because his trial at Goshen was not held until two months later. Upon his arrival in Goshen, the outlaw was cast into jail, ironed hand and foot, and chained to a ring in the floor.  A strong, round-the-clock guard was posted at the "grief hole" that opened into his cell.  The guard was under orders to shoot the Cowboy if an attack on the prison to effect his escape were likely to succeed.  Sheriff  Nicoll's precautions are easily understandable.  The prisoner had escaped from the Goshen jail more than a year before under circumstances that in retrospect, made the sheriff's blood run cold.

On Wednesday, January 13, 1779, Claudius Smith was taken forth for trial in the Court House in Goshen. Three indictments, all for theft, were lodged against him.  They were for burglaries in the houses of John Earle, Ebenezer Woodhull, and William Bell.

It is alleged that he conducted himself with admirable firmness during the course of the trial.  When the verdict of guilty was rendered and the sentence of execution by hanging was read, he was asked if he had anything to say in his defense.  “No,” he allegedly retorted. “If God Almighty can't change your hearts, I cannot.”  This statement, however, does not appear in the minutes of his trial, filed under PLP no. 1773 in the New York Hall of Records. 

On January 22, 1779, nine days after his trial, Claudius Smith marched with firm step toward the improvised gallows, comprising a cart over which a noose ominously dangled from a tree.  Crowds flocked to witness the execution of a man whose name had long terrorized their county and whose mere threat had prevented Colonel Jesse Woodhull (and many others, no doubt) from sleeping in his own house for months.

Dressed in a suit of rich broadcloth adorned with silver buttons, the Cowboy presented a noble appearance as he strode with a manly air toward the place in the western corner of the park, set for his execution.  His eyes were fixed intently upon Slate Hill east of Goshen, to ascertain some signs of an attempted rescue on the part of his comrades or particularly his two sons.  If throughout the term of his incarceration, he had entertained a hope of deliverance, he was sorely disappointed.  To his anxious eyes as they lingered hopefully on the distant prospect, none was to manifest.

As he was led, he bowed to several whom he knew in the crowd and evinced no outward sign of emotion.

Among the many legends about this Cowboy was his mother's early suspicion of criminal tendencies that lurked within his soul, even in his youth.  “Claudius,” she allegedly predicted, “you will die like a trooper’s horse, with your shoes on.”  Now, on the day of his demise, to rebuke his mother’s prediction, he calmly unbuckled and kicked off his boots.

The cart was withdrawn from under him, and he was strung into eternity- forever immortalized as a reprehensible felon.  If the American Revolution had failed and we were still colonists under the jurisdiction of the Crown, Claudius Smith would have died a martyr, and descendants may well point with pride to their noble heritage. 

After Claudius Smith was hung in the jail yard on ground that today comprises the Presbyterian Church Park, his death was immortalized by many objects connected with it.  An old Balm of Gilead tree, that remained standing until about 1920 when decay made its removal imperative, it was known thereafter as the “Hangman's Tree” A fifty seven pound iron weight that may still serve as a doorstep to the men's restroom of the Goshen Court House was once attached to one end of the noose in early Goshen hangings,  one of which might have been that of Claudius Smith's. The scaffold was allegedly still lying about in 1920 in the attic of the Goshen Court House. The first park bandstand was erected in 1855 over the very spot that Smith's feet first touched as he dropped to the ground from the scaffold and Smith's skull was allegedly bricked in at the keystone one over the Goshen Court House door, where a rough circular spot in the masonry just over the present court house betrays its location.

During the first half of the nineteenth century, tradition in the town of Monroe was rife with stories of caches filled with buried treasure.  During the Revolution, according to legend, the Cowboys had stolen at different times and among other things a large number of American muskets, pewter plates from governmental wagons, and a silver stand, the last from a British officer.  At the time that the plates were stolen, the gang was pursued, and one of the band was shot.  His bones, exposed to the winds and
snows of winter and the heat end rains of summer, lay bleaching for years wanting a friendly hand to bury them beneath the sod of the Clove or the rocks of the mountains.  The muskets and plates, according to tradition, were hidden in the mountains, and the silver stand was submerged in the mud of a spring in the vicinity.  During the first decade of the nineteenth century, a group of descendants of the refugee Cowboys arrived in Monroe from Canada with the location of the caches in writing. These treasure hunters included grandsons of Claudius Smith.  They remained in Monroe several days and searched diligently all the localities specified in the instructions of their fathers. They found nothing except the muskets, the stocks of which has been gnawed by mountain mice.

About 1823, two sons of Eduard Roblin, a Cowboy involved in the theft of the pewter plates, journeyed from Canada to Monroe, also with paternal instructions about the location of the caches. They remained several days and made a thorough search of the localities designated, but for all their pains, they found nothing. Soon after their return to Canada, the native who passed the story of these futile searches on to the recording historian of Orange County went  with others to re-explore the same localities in the mountains. They fished the spring and spent several days looking among the rocks and in the glens. Finding nothing, they finally gave up. In all probability, the caches had been emptied of loot by members of the gang who remained within the country or by their friends.  Legends, unlike outlaws, however, are blessed with longevity, and as recently as 1951, the editors of the New York Walk Book undoubtedly induced more forays with this intriguing sentence:

“Some of Smith’s loot was never recovered and is said to be still awaiting an exploring pick in the recesses of these hills.”


To view the original unedited version, and additional credits, click here.

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