The Historical past Behind Sleepy Hole: A Spooky Highlight on the Actual-Life Inspirations behind the characters, the locations, and the Headless Horseman

“The Legend of Sleepy Hole” stays probably the most pervasive and intriguing ghost tales of all time, and the first purpose for this are its deep roots in chance –

 its unusual connection to actual individuals and locations. Dracula and The Phantom of the Opera have lasted so lengthy for comparable causes, however whereas debates encompass the historic connections of these novels, nobody debates that Sleepy Hole is an actual place. The sternly stunning church peering from its perch above the black waters of the Pocantico River, the rust-colored grave markers of the Van Tassels and Martlings, the shady stillness of the Rockefeller State Protect, the gloomy crags of Raven Rock, and the winding, hilly bounds of the Outdated Albany Submit Highway testify to the story’s realism. There’s a sense of fact to it, grounded in place and historical past – and for good purpose. Whereas the precise story is basically an Americanization of three European folks tales (Burns’ “Tam O’Shanter,” Bürger’s “The Wild Huntsman,” and Musäus’ “The Legend of Rubezahl”), its roots are entangled in native tales, haunted spots, and twilight superstitions. On this article I’ll plunge deep into the historic inspirations behind the “Legend,” together with the stunning real-life Ichabod’s race with a sheeted horseman, the Galloping Hessian’s navy background, the 2 homes that impressed the Van Tassel Manor, and a number of the real ghost tales that Washington Irving snuck into his story – tales which Tarrytown locals nonetheless murmur at Halloween. 






 (All navy work by Dan Troiani)


“Hessians” had been German troopers loaned from the prince of Hesse-Kassel to reinforce international international locations’ armies. Hesse-Kassel was a small, forested state in Central Germany with little trade, so it relied on its soldiers-for-hire to spice up the in any other case agrarian financial system. The troopers had been absolute professionals – raised to struggle from youth – and had been amongst the very best educated fighters on this planet. They most famously partook within the battles of Lengthy Island (the place they terrified the Individuals with their talent and ferocity), Bennington (the place they had been massacred by vengeful militiamen), and Trenton (the place a small garrison was overwhelmed in an early morning raid). 30,000 Hessians fought within the conflict, and earned the worry and loathing of Patriot households who noticed them as a soulless killing machines pushed by greed moderately than advantage (in actuality, the prince — not the troopers — pocketed King George’s shillings).


The Headless Horseman is described solely as a “Hessian trooper” — a mounted soldier. Whereas the Hessians had no cavalry corps, they did have a number of troops of mounted rangers who steadily scoured the wild west no-man’s land of Sleepy Hole’s Westchester County. These dragoons– additionally referred to as chasseurs – had been a part of the Jäger Corps (pronounced “YAY-gur,” which means “huntsman” or “ranger”). Mounted rangers wore darkish inexperienced uniforms with apple-red lapels, inexperienced vests, and leather-based breeches with tall, black boots. They had been armed with a curved 33 inch-long metal saber (a light-weight cavalry sword with a easy “stirrup” hand guard and a razor sharp edge), horse pistols, and a carbine rifle.


Whereas the Horseman is often depicted in a fluttering black or scarlet cape, this was merely the literal cloaking machine of Brom Bones: cloaks restricted motion, turned entangled in timber and brush, and had been too clumsy for these excessive power scouts. As a substitute of a cape, the Horseman would have worn an overcoat in inclement climate, however most definitely simply wore his heavy, inexperienced wool jacket.


These troopers had been knowledgeable scouts, specializing in shock techniques, reconnaissance, raiding, and guerrilla warfare. Together with British gentle infantry, Hessian dragoons terrorized Patriots dwelling in Westchester County with their hit-and-run techniques, pace, violence, and horsemanship. 


 Regarding the Horseman’s decapitation, Irving solely notes that his “head was carried away by a cannonball throughout some anonymous battle.” There’s a spirited marketing campaign making an attempt to argue that this “anonymous” battle was the Battle of White Plains (28-30 October 1776) fought ten miles away from Sleepy Hole simply earlier than Halloween. Stories of Hessian artillerymen decapitated by Alexander Hamilton’s cannon fireplace are attention-grabbing, however Irving seemingly means precisely what he says, and since he later refers back to the “Battle of Whiteplains,” I hardly suppose he imagines a widely known conflict between Washington, Howe, and 1000’s of combatants to be a “anonymous” footnote in historical past (nor would the braggadocious veterans at Van Tassel’s get together who beloved describing their roles within the battle).


In the course of the conflict a small cannon was put in and fortified on a slope beside the churchyard (at present referred to as Battle Hill) overlooking the Albany Submit Highway (fashionable Route 9). Though no main battle ever befell below its watch, it was used to frighten off Crown Drive raiders. My guess is that Irving intends us to think about a squad of Jäger dragoons galloping down the street solely to take a broadside from the cannon hidden below the timber – possibly some pictures are exchanged, some sabers clatter, however after a couple of minutes of motion, the get together hurry on forsaking a mutilated comrade. What may very well be carried out apart from get the corpse out of the street? The place higher to get rid of it (and the inevitable stench) than within the churchyard thirty yards away?


 In reality, that is virtually precisely what occurred: the stays of a decapitated Jäger had been unceremoniously buried within the previous graveyard in an unmarked plot in 1778 (at present his physique has lastly been acknowledged with a easy brass pill studying: HESSIAN SOLDIER). Suitably sufficient, the physique is claimed to have been interred by the Van Tassel household as a stunning gesture of thanks. One winter evening in 1777 a band of Tories captured the Van Tassel brothers Peter and Cornelius (ardent Patriots and leaders within the rebel militia), torched their home, and left Elizabeth Van Tassel (Cornelius’ spouse) stranded with their toddler daughter Leah. Torn by pity, one of many Jägers within the get together rushed into the burning home and introduced again a feather mattresss and blankets to maintain the 2 from freezing, saving their lives.


When a decapitaed Jäger corpse was found on the aspect of the Submit Highway later that spring, Elizabeth paid for its burial. Whether or not the soldier was an foot soldier or a dragoon is not recorded, nor do we all know if his ghost was ever reported stalking the shades of Sleepy Hole. Whereas it’s tough to search out real folklore previous to 1820 testifying to an area perception in a Headless Horseman, Irving claims that the goblin was a real half of Tarrytown ghostlore. In line with his quick essay “Sleepy Hole” (included in his late-in-life assortment, “Wolfert’s Roost”), he discovered in regards to the Headless Horseman from an African American pensioner working at Carl’s Mill (the native haunted home, simply downriver of the Dutch Church, within the coronary heart of Sleepy Hole) and credit this anonymous folklorist with a lot of his childhood nightmares. 




Crane’s look is borrowed from Lockie Longlegs – a Scottish trainer whom Irving wrote about cheerfully to Walter Scott, utilizing a number of turns of phrase that might later present up in Ichabod’s description: “that worthy wight Lockie Longlegs, whose look I shall always remember striding alongside the profile of a knoll in his purple evening cap, together with his flimsy clothes fluttering about him.” The identify is important: Ichabod means “inglorious” (or: awkward, ugly, unimpressive) in Hebrew (1 Samuel 14:2-3), and naturally “the cognomen of Crane” suggests his gangly body. Whereas the identify was famously borrowed from a sturdy, grumpy-looking U.S. colonel who served with Irving in the course of the Conflict of 1812, the character is a portmanteau of a lovesick good friend named Jesse Merwin and the gangly Lockie. Merwin was a Kinderhook, NY schoolmaster who, in keeping with native custom, underwent a hazing ritual whereas he was courting a lady named Jane Van Dyck (a ritual referred to as a charivari which concerned being chased by mates dressed as ghosts with a view to inspire him to pop the query). Extra about that later (see: Brom Van Brunt). 


Ichabod’s New England background additionally has historic roots for post-Revolutionary New York. Industrious Yankees had been the bane of the Dutch settlers all through the colonial interval for a lot the identical purpose that Southerners grew to detest them as “carpetbaggers” in the course of the Reconstruction: New Englanders appeared to have a knack for making the most of a susceptible neighborhood and creating wealth off of their misfortunes. We are going to later be taught that Ichabod harbors each abilities since it’s his want to marry Katrina, liquidate her property, and transfer to Kentucky to arrange his fortune.


In reality, Brom’s alternative of weapon — the common-or-garden pumpkin — is a steadily missed allusion to Ichabod’s land of origin. Fairly than being a Halloweenish trope, the pumpkin was really a witty piece of rhetoric, urging the pumpkin-chomping Yankee to return whence he got here. In the present day we think about the Headless Horseman toting a flaming jack-o-lantern with its terrifying face of fireplace: it is because Irving lucked out by choosing the last word spooky gourd earlier than it had earned its status. Jack-o-lanterns, initially turnips, weren’t comprised of pumpkins till the 1840s (though Irving advantages profoundly for having unknowingly chosen the right vegetable to enthrone his story in Halloween ambiance).


The precise purpose that Irving selected the pumpkin is due to its cultural significance as a logo of New England: Yankees had been identified for adoring the versatile vegetable which grew simply of their chilly, sandy soil. I all the time inform my college students that throwing a pumpkin at a Yankee could be like throwing hunks of cheese at a Wisconsinite, hurling tea baggage at a Briton, or pelting a Floridian with oranges.





Though the identify is borrowed from Caterina Van Tassel, whose grave within the Burial Floor is singled out as that of the “actual” Katrina, this girl – center aged throughout Irving’s youth, and identified for her grounded sobriety – was not the inspiration for the sly coquette. This honor falls to Eleanor Van Tassel, her niece. Born in 1764, she grew up in Wolfert’s Roost (the mannequin for the Van Tassel Manor) and was briefly kidnapped by British troopers throughout a wartime raid (earlier than she and her feminine family members fought the attackers off). Spirited, feisty, flirtatious, and delightful, she was in her late twenties throughout Irving’s childhood and was aware of each him and his household.





Brom Van Brunt was impressed by two separate males, each blacksmiths named Brom. Probably the most notable is the conflict hero Abraham “Brom” Martling, who organized Tarrytown’s defenses in the course of the Revolution. Robust, heroic, beloved, and romantic, Martling epitomized the Sleepy Hole spirit. In his most well-known journey, he and a bunch of followers rowed a whaleboat from Tarrytown to the British strains in the midst of the evening and burned a Tory chief’s home to the bottom in retaliation for the burning of the Van Tassel brothers’ residence. They made it again to Patriot strains and have become prompt heroes for his or her daring act of defiance. Like Bones, Martling was the masculine very best of the world, the native referee, the admiration of youngsters, and the envy of males.


The opposite “Brom” was Kinderhook, NY’s Abram Van Alstyne. In line with native custom, this Brom helped encourage the thought of a prankster wrapped in sheets and mounted on a horse when he pranked the schoolmaster Jesse Merwin. Poor and low in confidence, Merwin was resisting his mates’ hints to pop the query to his long-suffering fiancée, Jane Van Dyck. Bothered by Merwin’s lack of initiative, mutual mates met and designed a charivari – a country hazing ritual meant to frighten ambling lovers into both marrying or name it quits. One evening, after leaving Jane’s home, Merwin discovered himself being adopted by a spectral horseman muffled in fluttering material. The stalking developed right into a race, with the shapeless specter abruptly disappearing in a cackle of acquainted laughter. Taking the trace, Merwin proposed and married Jane Van Dyck moderately than undergo a lifetime of comparable assaults.





The identify “Baltus” is a throwback to the household’s Zaandam origin: Baltus was a well-liked identify on this area as a result of it recommended the world’s supply of wealth: sawing Baltic timber for shipbuilders. Whereas there is no such thing as a exact historic mannequin for Baltus Van Tassel, he’s a conglomeration of varied Dutch landowners whom Irving admired as a baby. Open-hearted and open-handed, but unwaveringly dedicated to their traditions, communities, and households, these reasonable entrepreneurs fascinated Irving with their easygoing natures, lack of political bile, dedication to neighborhood, and receptiveness to strangers. The closest mannequin we’ve got is Jacob Van Tassel, father of the spirited Eleanor and one-time proprietor of Wolfert’s Roost (the mannequin of the Van Tassel Manor and later dwelling of Washington Irving, who would rework it into Sunnyside).







A official Sleepy Hole ghost: mentioned to hang-out Raven Rock – a craggy glacial scar named for its eerie attraction of the funereal birds – this ghostly girl in white apparel has two totally different backstories. The primary is that she was a determined single mom gathering firewood to warmth her cottage earlier than a blizzard, however that she was caught off guard and froze to dying huddling below Raven Rock’s jagged partitions. The opposite states that she was a younger lady who had organized to elope with a British officer; she arrived in her gown on the Rock on the appointed date, however he didn’t seem – as an alternative a blizzard started to fall, however she remained steadfast to the appointment, till dying overtook her. Both manner, the so-called “Woman in White” moans pitiably earlier than harsh snow storms, and has been noticed in Sleepy Hole since colonial instances.





 (All navy work by Dan Troiani)


In the course of the Revolutionary Conflict, Westchester County was a sensible wasteland of vigilantism, wild west justice, pillaging, raids, heroics, villainy, and anarchy. Sandwiched between the Patriot strains at Peekskill and the British strains at Kingsbridge, it turned known as “the Impartial Floor,” however was actually a wild no-man’s land of lawlessness. Dozens of brutal skirmishes had been recorded between Patriot and Loyalist militias, at the very least one full-scale battle at White Plains, and numerous raids on civilians by the so-called Skinners (Patriot-allied bandits) and the Cowboys (British-allied raiders) – both of whom might change loyalties for cash. Tarrytown was raided by the British at the very least twice and shelled as soon as, and a cannon was fortified simply south of the Outdated Dutch Church to guard Philipsburg Manor from assaults by Hessian troopers (the infamous Jäger dragoons) and British gentle infantry. Many harrowing adventures befell within the space, together with the well-known 1777 raid on the Van Tassel farm (the place the 2 Van Tassel brothers had been captured by a blended pressure of Hessians and Loyalists, their home burned, and their cattle stolen; in the meantime younger Elizabeth Van Tassel’s daughter Leah was saved from the fireplace by a Hessian soldier, who additionally saved the 2 from freezing by bringing them a quilt).


 Probably the most well-known native battle between the Crown Forces and Patriots is the Battle of White Plains. Ten miles east of Sleepy Hole, White Plains is the county seat of Westchester, and was the location of an indecisive battle between the Continental Military (below George Washington) and the British (below William Howe) and their Hessian allies (led by Leopold von Heister). From October 27-30, 1776, the Individuals held floor on and round Chatterton Hill whereas the Hessians charged their positions. The German battalions had been mangled by a gun battery commanded by Alexander Hamilton, and had been delayed when a horrible storm broke out over the battlefield. Underneath the quilt of the tempest, the Individuals retreated on Halloween evening, leaving Westchester to the British, and crossing the Hudson.




 Sleepy Hole’s most well-known ghost (with a head) is the weeping determine of the dashing Main John Andre, a younger, formidable, and tremendously unfortunate British spy-master who was captured outdoors of Tarrytown coming back from a gathering with Benedict Arnold. Their plan was to give up the Hudson River fortress at West Level to the British. In alternate, Arnold – offended at being handed up for promotions – hoped to change into a British hero. As a substitute, the plan was found, Arnold fled to British strains, and the dashing John Andre was hanged as a spy. A lot mourned (on either side: Andre was good-looking and achieved, and rapidly made mates together with his captors), he was thought of a tragic sacrifice to Arnold’s treachery (somebody, in spite of everything, needed to hold for it). Since his execution, Andre has been mentioned to hang-out the world of his seize. The towering tulip tree which bore his identify — a couple of soccer discipline’s size south of Andre Brook — was lengthy mentioned to be haunted by the sight and/or sound of a weeping man, and the bridge that spanned Andre Brook (now in Patriots’ Park), the place the militiamen captured him, remains to be mentioned to be haunted. In line with legend, Andre’s ghost — and sobbing — will dissipate if you happen to ask it “What get together are you from?” — the problem issued to him from the American troopers. In actual life he responded in truth that he was with the British (mistaking the Patriots for Loyalists) — a response that his ghost nonetheless appears to remorse. Just like the Hessian (and later Ichabod), Andre contributes to the “legend” of Sleepy Hole – the narrative that meddlers, invaders, mercenaries, schemers, oppressors, and raiders of all stripes might be handled firmly, and expelled (if not destroyed)






 The historic Sleepy Hole shouldn’t be the present village, however the valley of the Pocantico River, simply east of the fashionable suburb. Fortunately, a lot of this land is at present assigned to parkland (Douglas Park and the Rockefeller State Park), the place its quiet, peace, and wonder can nonetheless be appreciated. The Pocantico River – a tributary of the Tappan Zee and the black, effervescent stream that Ichabod will race to within the climax – runs northeast from the Hudson River, chopping its manner between the hills that outline Sleepy Hole, splashing over boulders and fallen timber. An odd, jealous effort has been made by the city of Kinderhook, NY to argue that Sleepy Hole by no means existed and that it was impressed by their sleepy upstate village. For proof they provide that Sleepy Hole, NY was referred to as North Tarrytown till the 1990s, that the schoolmaster Merwin and the blacksmith Brom Van Alstyne referred to as Kinderhook dwelling, and that Irving steadily journeyed there.


The argument is fragile at greatest, pathetic on the worst: not solely did Sleepy Hole exist on maps relationship again to earlier than the English took New York from the Dutch, however — as I talk about in “The Outdated Albany Submit Highway” — Irving laces his story liberally with precise landmarks from Andre Brook and Raven Rock to the Outdated Dutch Church and the “rising floor” of Sleepy Hole Excessive College. It’s true that North Tarrytown selected to vary its identify and that it was by no means thought of Sleepy Hole, however “Sleepy Hole” — the peaceable valley downriver from the church — is conveniently situated a mile and a half from the middle of the city which now bears its identify: a quiet, shady vale made up of rolling hills, whispering timber, and monolithic boulders. 




(Annotations on the Map by Michael Kellermeyer)


Ichabod’s journey dwelling strains up kind of with fashionable Route 9, one of many oldest highways within the nation. Primarily based on an previous Indian path, the street was later widened and served as the primary artery from New York to Albany, operating parallel with the Hudson. Ichabod rides dwelling from the previous Van Tassel home in Irvington, north via the tangles of Wildey’s Swamp, over the bridge at Andre Brook, up the slope the place the Sleepy Hole Excessive College at present sits. From this spot – the place Ichabod sees the Horseman in stark reduction in opposition to the sky – he plunges down Route 9 and makes an attempt to show down Bedford Highway (the previous Sleepy Hole Highway), however Gunpowder retains left and leads him in the direction of the church. From right here the historic Albany Submit Highway made an S-shaped curve whereas fashionable Route 9 retains going straight.


Ichabod’s flight would have taken him down Route 9 till New Broadway (the trail of the Outdated Submit Highway), the place it could have curved close to fashionable Crane Avenue, pounding via what’s now a collection of personal lawns, west in the direction of the Pocantico, and throughout the bridge (initially positioned some 200 yards east of the present “Headless Horseman Bridge”). From right here the street would have swung west (operating parallel to the river and simply south of the Church), earlier than crooking north once more (finishing the S-shape) and hooking up once more with fashionable Route 9, operating previous the Church’s doorways and north in the direction of Albany.   




The Van Tassel Manor shouldn’t be based mostly on one single property, however on a mix of locations. Geographically and traditionally, it’s based mostly on Wolfert’s Roost (later Sunnyside) in Irvington, New York, three and a half miles from the Outdated Dutch Church. Wolfert’s Roost was owned by Jacob Van Tassel and his daughter Eleanor, however as a stone farmhouse it doesn’t match the architectural particulars of Baltus’ sprawling property. The Van Cortlandt Manor in close by Croton-on-Hudson is the very image of Balt’s welcoming Dutch stronghold with its yawning piazza, rolling farmland, and chic, colonial inside. In the end, in Irving’s creativeness, the Van Tassels dwell within the neighborhood of Wolfert’s Roost, in a manor that resembles the Van Cortlandt property.





Known as Main Andre’s Tree, this historic landmark was so huge that the Albany Submit Highway break up in two and skirted it (a notable factor in an age when timber had been seen as inconveniences to the Manifest Future spirit of most Individuals, and infrequently spared the axe after they stood in the best way of human engineering). An enormous 111 ft tall, 29 ft across the base, and 106 ft in diameter on the crown, it was an awe-inspiring sight and was identified for the numerous superstitions regarding it.





The gloomy hang-out of the Girl in White can nonetheless be discovered by hikers and sightseers. Raven Rock is situated on Buttermilk Hill contained in the Rockefeller State Park; this cruel-looking formation was additionally referred to as “Spook Rock” by locals, and is only a few miles away from the Outdated Dutch Church.





Wiley’s (or extra precisely Wildey’s) Swamp (a part of property as soon as owned by Caleb Wildey) – a marshy ravine – has lengthy since been drained, though the rivulet that fed it (now referred to as Andre Brook) nonetheless bubbles via Patriots’ Park in Tarrytown at present. Named for the three militiamen who arrested Andre and resisted his bribes, the park can be remembered as being the spot the place Ichabod first encounters the Headless Horseman. Patriots’ Park is .7 miles from the Outdated Dutch Church the place the race will in the end conclude. The unique bridge – the three tough logs – which Ichabod struggles to get Gunpowder to cross was a couple of dozen yards east of the stone bridge which at present spans Andre Brook, and their first encounter most likely befell simply east of Patriot’s Park, on the opposite aspect of Route 9.





At the moment there are two bridges close to the Dutch Church which span the Pocantico: the official Headless Horseman Bridge (an uninspiring multilane concrete construction simply south of the church on Route 9), and a romantic picket construction with trusses and railing comprised of tree branches (half a mile downriver of the boring fashionable bridge). Neither of those are within the spot the place the unique Headless Horseman bridge lay.


There have been 5 totally different bridges since colonial instances, and the street itself has been moved at the very least 3 times. The bridge within the story would have been situated some a number of hundred yards east (downriver) of the present fashionable construction spanning Route 9. This bridge is claimed to have been plain (bordering on ugly), with out architectural gildings or ornamentations. {A photograph} of one of many bridges which existed throughout Irving’s lifetime (however after the colonial construction had been dismantled) exhibits a sagging picket span with a triangular assist on both aspect.


It was by no means, because the Disney model popularized, a lined bridge.





The Outdated Dutch Church stays the second oldest church in New York, based in 1685 by the Dutch settlers of Tarry City. Its Outdated Burial Floor incorporates the stays of many fashions for Irving’s characters in addition to Irving himself. Its iconic stone partitions, bell tower, and peaked home windows have made it a logo of the world since colonial days. 


Yow will discover our assortment of Irving’s greatest ghost tales (together with the annotated, illustrated “Legend of Sleepy Hole”) HERE





“Legends and Lore of Sleepy Hole and the Hudson Valley,” by Jonathan Kruk

“Historic Sketches of the Romer, Van Tassel, and Allied Familes,” by John Lockwood Romer


“The Place Names of Historic Sleepy Hole and Tarrytown,” by Henry Steiner


 (All navy work by Dan Troiani)







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