Legends and Lore of Sleepy Hollow and the Hudson Valley

by Jonathan Kruk

  Fairy tale traditions transported from Europe to America, like folk music, were adapted to the new landscape. Once upon a time, in the Old World, people left fields fallow for the little people. Peasants gave gifts in return for medicine from the fairies. Caves and crags were left open for the ancient enchanted races. Passersby sang psalms to ward off those old ones. The New World, especially around Sleepy Hollow, developed its own cautionary ways. Thus tip your hat to salute the imps of Donder-Berg. Sing a psalm like Ichabod Crane’s to frighten away ghosts. And heed the wailings of the White Lady who cries before coming storms.

  The protective nature spirits of Old World White Ladies reappear indeed in Sleepy Hollow’s folklore. Originally these nature fairies captivated lovers, gave gifts of precious stones and spread seeds that eventually became spirits of the wind. Around Sleepy Hollow, heartbreak led them to sound storm warnings.

  The primordial White Lady emerges in another epic story: the Legend of King Arthur. The chieftain who first united tribal Britain against Saxon invaders had a “white phantom” or “apparition” of a wife. Guinevere translates from the ancient Brythonic as “Gwenhwyvar,” meaning white ghost. Clearly, Arthur’s queen foreshadows Sleepy Hollow’s White Ladies.

  Across the ocean, colonists frightened by the wilderness felt something unearthly in the winds off the Hudson. There’s a Native story of an aggravated young woman transformed, like a New World Daphne, into a manitou. Following her to Raven Rock, some European women ignore or miss the Native spirit’s warning. They become fairy-ghosts themselves, wailing new warnings in the wind.

  The Dutch settlers of the lower Hudson Valley may have been the “hard blond traders” described by Carl Carmer. Pragmatists when facing the raw wilderness, strange Native peoples and rival European powers, the Dutch also encountered things unknown. They never experienced the dense forests, jagged palisades and misty coves found along the Hudson. The Tappan Zee’s sudden sail-sheering wind, the moaning in the hills and the gloomy atmosphere turned them back to folklore from home for explanations. Thus new phenomena encountered in the New Netherlands made White Ladies at Raven Rock, imps in the Highlands and other spirits too.

  Finally, the collection of spirit lore that Ms. Cecelia Kingston’s class gathered indicate Sleepy Hollow remains a place fraught with “marvelous tales of ghosts and goblins, and haunted fields, and haunted brooks, and haunted bridges, and haunted houses.” One relatively recent report, however, shows a return of some Old World fairy tale. The son of John D. Rockefeller Jr., son of one of the richest men of all time, found Raven Rock romantic. Sunshine and lush foliage with a river view made his “secret love-seat.” Raven Rock today rises above the noise and dense suburban development of Westchester County. Apparently, the White Lady restored it to idyllic fairy refuge: “If ever I should wish for a retreat, whither I might steal from the world and its distractions, and dream quietly away the remnant of a troubled life, I know of none more promising than this little valley” (TLSH, 3).

  Chapter 6

  “THE TRAGICAL STORY OF THE UNFORTUNATE ANDRE”

  It was connected with the tragical story of the unfortunate Andre, who had been taken prisoner hard by; and was universally known by the name of Major Andre’s tree. The common people regarded it with a mixture of respect and superstition, partly out of sympathy for the fate of its ill-starred namesake, and partly from the tales of strange sights, and doleful lamentations, told concerning it (TLSH, 60).

  The Hudson River served as the stage for nation-shaping ordeals during the American Revolutionary War. Decisive battles along the upper river near Saratoga provided “the turning point of the Revolution.” Significant clashes occurred at Harlem Heights, Pelham, White Plains, Stony Point, the Hudson Highlands and Kingston. The lower Hudson Valley endured terrible raids by both Loyalist Cow-Boys and Patriot Skinners. When George Washington declared West Point on the Hudson “the key to the continent,” both Congress and the British agreed. Two immense chains were stretched across the river to figuratively and literally hold the new nation together. Redcoat forces under General Sir Henry Clinton cut the first like a “Yankee pumpkin vine.” Links later set by the Polish Patriot and engineer Thaddeus Kosciuszko held against British warships like “Washington’s watch chain.” When Washington’s best fighting general, Benedict Arnold, turned traitor, he slipped that strategic key to the entire American bid for independence to a young British major disguised as a traveling merchant. Thus beneath branches of a Sleepy Hollow tulip tree unfolds the tragic story of John Andre.

  The tale of Arnold and Andre remains the most intriguing event of the American Revolution, especially to those in the Hudson Valley. Today the region has two Andre monuments, an Andre Brook, a historic trail and a memorabilia room devoted to the incident at Sleepy Hollow’s historical society. Now, around Halloween, an animatronic effigy of John Andre is hanged at Philipseburg Manor. Every hamlet and house Andre visited on his fateful journey boasts a marker, a plaque and a story. Further, John Andre’s ghost pervades the area, particularly in Sleepy Hollow.

  A TRAGIC STORY UNFOLDS

  He organized an intrepid assault on Quebec, helped commandeer Fort Ticonderoga, saved the American cause at Lake Champlain and heroically led American forces to victory at Saratoga. Benedict Arnold had horses shot out from under him, suffered bullet wounds to the leg and was arguably the new nation’s top fighting general. Congress, however, belatedly recognized Arnold’s battlefield prowess. They actually court-martialed him for using troops to move his personal goods in Philadelphia. George Washington “would have been much happier in an occasion of bestowing commendations” on Arnold. Congress ordered their commander in chief to reprimand Arnold’s actions as “imprudent and improper.” Feeling overlooked and outraged, Arnold believed Congress ruined the Revolution and his career. His young Loyalist wife, Peggy Shippen, then suggested Arnold go turncoat. The jilted general agreed. Peggy sought help from an old flame, the British adjutant general, Major John Andre. They conspired in 1780 to make Arnold a British general, hand America’s fortress at West Point to the Redcoats and put an end to the foolhardy American bid for independence.

  Handsome, ruthless, endearing, ambitious, artistic and careless, John Andre coordinated and executed the plot. Tragically, misfortune and miscalculation marred Andre’s every move. Still, this genteel British officer came tantalizingly close to accomplishing his mission. Alas, three Skinners caught the fated major a few miles from his destination. They apprehended him right beneath a huge tree on the Sleepy Hollow/Tarrytown line. Andre suffered the hangman’s noose. Arnold made brigadier, plus £6,315 sterling. The Revolution succeeded.

  Ghost hunters claim they may detect a supernatural presence when someone dies unjustly or with unfinished business. John Andre’s strange case meets both criteria. This rising officer felt Arnold and circumstance induced him to act like a spy. Many like Alexander Hamilton and the Marquis de Lafayette agreed. They put forth Andre as a man worthy of a far better fate.

  The visionary nineteenth-century writer George Lippard, in his Washington & His Generals, or Legends of the Revolution, said:

  Arnold escapes the hand of vengeance now. No, flushed with triumph, he goes on to complete his career of blood. He will gather gold—renown, aye favor from the hands of his King. But in the hour of his proudest triumph, even when he stands beside the Throne, one form, invisible to all other eyes, will glide through the thronging courtiers, and wither him, with its pale face, its white neck polluted by the gibbet’s rope, its livid lip trembling with a muttered curse—the Phantom of John Andre!

  John Andre, the up-and-coming officer, was distinguished by unswerving service on the battlefield and inspiring performances on stage. Born in London to French Huguenot parents and raised in a merchant’s home, Andre excelled at various arts and languages. Heartbroken after the family of his beloved, Honora Sneyd, rejected his marriage proposal, Andre bought an officer’s commission in the British army. He shipped out with the regiment se
nt to quell restless New England colonies in the early 1770s.

  Andre fought bravely in Canada against American forces under Generals Richard Montgomery and Benedict Arnold. Captured and held in grim conditions, Andre soured on the rebellious colonists. He wrote in a letter to his friend, the poet Anna Seward, complaining that Americans “stripped [me] of everything except the picture of Honora, which I concealed in my mouth. Preserving this yet [I] think myself fortunate.” A prisoner of war exchange in Pennsylvania returned Andre to active duty serving as an aide to Major General Charles Grey. He participated in “No-Flint” Grey’s bayonet-driven assaults on American forces at Brandywine, Germantown and Monmouth and at massacres in Old Tappan and Paoli.

  During the British occupation of Philadelphia in the summer of 1778, Andre wrote, costumed and designed a theatrical extravaganza called the Mischianza. There he engaged in a flirtatious relationship with Peggy Shippen, an irresistible Tory eighteen-year-old. The next year, however, she married thirty-eight-year-old General Benedict Arnold.

  Andre’s efforts in both the theaters of war and stage soon earned him the post of adjutant general under Sir Henry Clinton, commander of Britain’s North American forces. When her new husband soured on Congress and the American Revolution, Peggy knew just who to contact. John Andre could help with her disgruntled Benedict.

  BETRAYING BENEDICT

  Benedict Arnold in America is a synonym for traitor. In September 1780, after years of valiant fighting for American independence, Arnold abandoned his new country and comrades. He accepted his enemy’s offer to become a brigadier general. Scholars, historians and folklorists in the Hudson Valley still debate why Arnold became a turncoat. Many state that had Arnold not switched sides, his heroics would have ranked second only to George Washington’s.

  During the war’s first years, Benedict Arnold not only fought with distinction, but he also secured the new United States. He led, along with Ethan Allen, the attack on Fort Ticonderoga. While Allen held a drunken victory celebration with his Green Mountain Boys, Arnold commandeered the cannons that Henry Knox later hauled to defend Boston. Arnold spearheaded daring and arduous assaults on Quebec City and Montreal. His brilliant tactics at naval battle of Valcour Island prompted historian Alfred T. Mann to declare, “When Benedict Arnold on Lake Champlain by vigorous use of small means, obtained a year’s delay for the colonists, he compassed the surrender of Burgoyne in 1777.”

  Arnold’s brash leadership on the battlefields near Saratoga and his countersiege against St. Legers’ attack on Fort Stanwix foiled the famed British “three-pronged attack.” A strategy devised by General John Burgoyne to divide the colonies along the Hudson River, Arnold stopped two of the three British assaults. Granted, the other American commander at Saratoga, General Horatio Gates, benefited from carefully planned fortifications and troop placements made by Kosciuszko. It was Arnold, however, on a brown charger, who literally led the most decisive attack. American Continentals and militia alike found courage to fight by following Arnold on to victory. “Gentleman Johnny” Burgoyne sniffed, when surrendering to “Granny” Gates at Saratoga, “The fortunes of war have made me your prisoner.” Actually, it was the misfortunes of Benedict Arnold. When Johnny and Granny sat down together to dine after the ceremony, Arnold lay on a hospital table begging to have his twice-wounded left leg spared from the surgeon’s saw. Gates replied to Burgoyne, “I shall always be ready to testify that it [the British defeat] has not been through any fault of your Excellency.” Gates’s report to Congress and George Washington on the American victory at Saratoga omitted Arnold’s action, thus planting in the egotistical Benedict the seed of treason.

  Later, after his marriage, court-martial and reprimand in Philadelphia, Arnold accepted Peggy’s scheme to abandon the United States as a failed experiment in mob rule. Secret letters to Major Andre set up the deal. Arnold would weaken America’s fortress at West Point and remove a link from Washington’s watch chain. He’d ensure the Hudson fell into British control, switch sides and receive about £20,000 sterling for his efforts. They felt their plot to end the American rebellion would make Andre a general and Arnold a viceroy! Lippard, however, divined:

  The Phantom will poison his life…As he presses his wife to his lips, that pale face will glide between, muttering that soundless curse.

  To escape that Phantom, he will hurry from place to place! Now in the snows of Canada, now amid the palm groves of the Southern Isles, now on ship-board, now on shore—still John Andre’s ghost will silently glide by his side.

  Crossing the Hudson, 1780 ink on paper. Copy of sketch by Major John Andre, from Harper's Monthly, April 1876. From the collection of the Highland Studio, Inc., Cold Spring, NY.

  Ichabod Crane, en route to his ill-fated encounter with the Headless Horseman, cringed upon approaching “Andre’s tree.” Worried Andre’s ghost would glide by when the schoolmaster “approached this fearful tree, he began to whistle.” The massive tulip tree stood near “Wiley’s Swamp” just below the Albany Post Road. The whole place was fraught with “mourning cries and wailings.”

  The spot where the American Skinners John Paulding, David Williams and Isaac Van Wart captured John Andre is now marked with a monument and a park. Here people sense an invisible presence of the ghost. The frightened schoolmaster in The Legend, nevertheless, “passed the tree in safety.” This took him off guard for the coming encounter with the region’s dominant spirit. Andre’s spirit, however, is known to haunt in the early morning. Ichabod approached just after “the dead hush of midnight.” The Yankee schoolmaster’s relief when escaping this Sleepy Hollow specter begs the question: what is “the tragical story of the unfortunate Andre”?

  ANDRE’S JOURNEY

  The reverberation of cannon fire disrupted a clandestine meeting in the shadows of Long Clove Mountain. “Gustavus” pressed into the hands of “John Anderson” a sheaf of six pages. ‘Take these to your superior. They show how to take the American fortress at West Point.” Major John Andre objected, “I could be taken as a spy with these on my person.” General Arnold scribbled a pass, permitting John Anderson safe passage through all posts to White Plains. Smiling, British major John Andre bid farewell to American general Benedict Arnold. Dashing down the steep Hudson Highland hill, Andre hoped the shots had not come from The Vulture.

  The British warship The Vulture was set off Croton Point to transport Andre after he met and confirmed Arnold’s readiness to turn coats. One local legend says a slave and an indentured servant spied the warship and alerted an American colonel, Livingston. Lacking Arnold’s approval, Livingston allowed the militia to haul a cannon down to the point. The locals fired, forcing the ship to withdraw from Dobbs Ferry without Andre.

  Fate then doomed Andre. Joshua Hett Smith, Andre’s local Loyalist guide, convinced the British major to take another course back to New York City. “You are a target in your Redcoat uniform,” Smith noted while getting the major to don a disguise of a round beaver felt cap and claret cloak. Smith and his servant rowed John Anderson across the Hudson to Verplanck. Against orders, he carried enemy papers, incognito, into a no-man’s land.

  Wending his way south through the no-man’s land of Upper Westchester, Major John Andre, adjutant general to Sir Henry Clinton, commander in chief of King George’s Third’s Expeditionary Force in North America, anxiously sought Dobbs Ferry. Andre and Smith spent a fretful night at the home of Andreas Miller, near Pines Bridge (Yorktown Heights). Following a couple of close encounters with wary American officers, Smith abandoned Andre, leaving the Englishman to find his way in a county with signs reading, “Dish his di Roode toe de Kshing’s Farry.”

  The sentry at Pines Bridge, the boundary between British lower and American upper Westchester, warned, “Take heed of the Cow-Boys down there.” Andre agreed, showing his pass from Arnold, but he hoped he’d find one of those Loyalist bands driving stolen cattle to British troops in New York City. He forgot about the Patriot Skinners out to make them stop.


  He broke fast with a bowl of mush given to him by a Dutch woman at the Underhill House. Evidently, he also accepted a peach from a child near a well. Several miles later, his horse clattered over the little bridge by the Old Dutch Church in Sleepy Hollow. Glimpsing through autumn-tinged trees the expansive Tappan Zee, Andre took heart. Dobbs Ferry was near! A band of Skinners, however, alerted nearby too.

  The one clad in a red and green coat he swiped to escape from a Hessian guard stepped forward, aiming a musket. Two other Skinners in plain hunter’s frocks hid in the brush, while a handful of others played cards in the next field. They spied a horseman in a common round beaver cap and cloak with military trimmed boots. Relieved to see the coat of a Hessian ally, Major Andre called out, “I see you are with our party!”

  The one in the Hessian coat, John Paulding, replied, “What party are you from?”

  Andre again considered the gunman’s clothes and believed he had finally landed in helping hands. He answered Paulding, “The lower party!”

  Paulding gave a quick nod to his compatriots, Isaac van Wart and David Williams, and told the rider they were all with the lower party too.

  “Thank God!” Andre gushed. “I am a British officer on particular business in this country and cannot be detained. I must get to General Clinton! Here, let me prove it to you.”

  The rider produced a fine pocket watch, indicative of his status. “Now, I warn you. Do not detain me for one more minute.”

  Paulding gave another subtle signal to his compatriots. They stepped up next to the rider. One shot a hand onto the horse’s bridle. The other went for the stirrup. Paulding ordered, “Climb down off your mount. We are American Patriots!”