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The History Behind Sleepy Hollow: A Spooky Spotlight on the Real-Life Inspirations behind the characters, the places, and the Headless Horseman

“The Legend of Sleepy Hollow” remains one of the most pervasive and intriguing ghost stories of all time, and the primary reason for this are its deep roots in possibility –

 its uncommon connection to real people and places. Dracula and The Phantom of the Opera have lasted so long for similar reasons, but while debates surround the historical connections of those novels, no one debates that Sleepy Hollow is a real place. The sternly beautiful 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 Preserve, the gloomy crags of Raven Rock, and the winding, hilly bounds of the Old Albany Post Road testify to the story’s realism. There is a sense of truth to it, grounded in place and history – and for good reason. While the actual tale is largely an Americanization of three European folk tales (Burns’ “Tam O’Shanter,” Bürger’s “The Wild Huntsman,” and Musäus’ “The Legend of Rubezahl”), its roots are entangled in local tales, haunted spots, and twilight superstitions. In this article I’ll plunge deep into the historical inspirations behind the “Legend,” including the surprising real-life Ichabod’s race with a sheeted horseman, the Galloping Hessian’s military background, the two houses that inspired the Van Tassel Manor, and some of the genuine ghost stories that Washington Irving snuck into his story – tales which Tarrytown locals still murmur at Halloween. 






 (All military paintings by Dan Troiani)


"Hessians" were German soldiers loaned from the prince of Hesse-Kassel to augment foreign countries’ armies. Hesse-Kassel was a small, forested state in Central Germany with little industry, so it relied on its soldiers-for-hire to boost the otherwise agrarian economy. The soldiers were absolute professionals – raised to fight from youth – and were amongst the best trained fighters in the world. They most famously partook in the battles of Long Island (where they terrified the Americans with their skill and ferocity), Bennington (where they were massacred by vengeful militiamen), and Trenton (where a small garrison was overwhelmed in an early morning raid). 30,000 Hessians fought in the war, and earned the fear and loathing of Patriot families who saw them as a soulless killing machines driven by greed rather than virtue (in reality, the prince -- not the soldiers -- pocketed King George's shillings).


The Headless Horseman is described only as a "Hessian trooper" -- a mounted soldier. While the Hessians had no cavalry corps, they did have several troops of mounted rangers who frequently scoured the wild west no-man's land of Sleepy Hollow's Westchester County. These dragoons– also called chasseurs – were part of the Jäger Corps (pronounced “YAY-gur,” meaning “huntsman” or “ranger”). Mounted rangers wore dark green uniforms with apple-red lapels, green vests, and leather breeches with tall, black boots. They were armed with a curved 33 inch-long steel saber (a lightweight cavalry sword with a simple "stirrup" hand guard and a razor sharp edge), horse pistols, and a carbine rifle.


While the Horseman is usually depicted in a fluttering black or scarlet cape, this was merely the literal cloaking device of Brom Bones, and not likely to have been worn by a dragoon on patrol: cloaks restricted movement, became entangled in trees and brush, and were too clumsy for these high energy scouts. Instead of a cape, the Horseman would have worn an overcoat in inclement weather, but most likely just wore his heavy, green wool jacket.


These soldiers were expert scouts, specializing in shock tactics, reconnaissance, raiding, and guerrilla warfare. Along with British light infantry, Hessian dragoons terrorized Patriots living in Westchester County with their hit-and-run tactics, speed, violence, and horsemanship. 


 Concerning the Horseman's decapitation, Irving only notes that his "head was carried away by a cannonball during some nameless battle." There is a spirited campaign trying to argue that this “nameless” battle was the Battle of White Plains (28-30 October 1776) fought ten miles away from Sleepy Hollow just before Halloween. Reports of Hessian artillerymen decapitated by Alexander Hamilton’s cannon fire are interesting, but Irving likely means exactly what he says, and since he later refers to the “Battle of Whiteplains,” I hardly think he imagines a well-known clash between Washington, Howe, and thousands of combatants to be a "nameless" footnote in history (nor would the braggadocious veterans at Van Tassel's party who loved describing their roles in the battle).


During the war a small cannon was installed and fortified on a slope beside the churchyard (today called Battle Hill) overlooking the Albany Post Road (modern Route 9). Although no major battle ever took place under its watch, it was used to frighten off Crown Force raiders. My guess is that Irving intends us to imagine a squad of Jäger dragoons galloping down the road only to take a broadside from the cannon hidden under the trees – maybe some shots are exchanged, some sabers clatter, but after a few minutes of action, the party hurry on leaving behind a mutilated comrade. What could be done other than get the corpse out of the road? Where better to dispose of it (and the inevitable stench) than in the churchyard thirty yards away?


 In fact, this is almost exactly what happened: the remains of a decapitated Jäger were unceremoniously buried in the old graveyard in an unmarked plot in 1778 (today his body has finally been acknowledged with a simple brass tablet reading: HESSIAN SOLDIER). Suitably enough, the body is said to have been interred by the Van Tassel family as a surprising gesture of thanks. One winter night in 1777 a band of Tories captured the Van Tassel brothers Peter and Cornelius (ardent Patriots and leaders in the insurgent militia), torched their house, and left Elizabeth Van Tassel (Cornelius' wife) stranded with their infant daughter Leah. Torn by pity, one of the Jägers in the party rushed into the burning house and brought back a feather mattresss and blankets to keep the two from freezing, saving their lives.


When a decapitaed Jäger corpse was discovered on the side of the Post Road later that spring, Elizabeth paid for its burial. Whether the soldier was an foot soldier or a dragoon isn't recorded, nor do we know if his ghost was ever reported stalking the shades of Sleepy Hollow. While it is difficult to find genuine folklore prior to 1820 attesting to a local belief in a Headless Horseman, Irving claims that the goblin was a genuine part of Tarrytown ghostlore. According to his short essay “Sleepy Hollow” (included in his late-in-life collection, “Wolfert’s Roost”), he learned about the Headless Horseman from an African American pensioner working at Carl’s Mill (the local haunted house, just downriver of the Dutch Church, in the heart of Sleepy Hollow) and credits this nameless folklorist with many of his childhood nightmares. 




Crane’s appearance is borrowed from Lockie Longlegs – a Scottish teacher whom Irving wrote about cheerfully to Walter Scott, using several turns of phrase that would later show up in Ichabod’s description: “that worthy wight Lockie Longlegs, whose appearance I shall never forget striding along the profile of a knoll in his red night cap, with his flimsy garments fluttering about him.” The name is significant: Ichabod means “inglorious” (or: awkward, ugly, unimpressive) in Hebrew (1 Samuel 14:2-3), and of course “the cognomen of Crane” suggests his gangly frame. While the name was famously borrowed from a robust, grumpy-looking U.S. colonel who served with Irving during the War of 1812, the character is a portmanteau of a lovesick friend named Jesse Merwin and the gangly Lockie. Merwin was a Kinderhook, NY schoolmaster who, according to local tradition, underwent a hazing ritual while he was courting a woman named Jane Van Dyck (a ritual called a charivari which involved being chased by friends dressed as ghosts in order to motivate him to pop the question). More about that later (see: Brom Van Brunt). 


Ichabod's New England background also has historical roots for post-Revolutionary New York. Industrious Yankees were the bane of the Dutch settlers throughout the colonial period for much the same reason that Southerners grew to loathe them as “carpetbaggers” during the Reconstruction: New Englanders seemed to have a knack for taking advantage of a vulnerable community and making money off of their misfortunes. We will later learn that Ichabod harbors both talents since it is his desire to marry Katrina, liquidate her estate, and move to Kentucky to set up his fortune.


In fact, Brom's choice of weapon -- the humble pumpkin -- is a frequently missed allusion to Ichabod's land of origin. Rather than being a Halloweenish trope, the pumpkin was actually a witty piece of rhetoric, urging the pumpkin-chomping Yankee to go back whence he came. Today we imagine the Headless Horseman toting a flaming jack-o-lantern with its terrifying face of fire: this is because Irving lucked out by picking the ultimate spooky gourd before it had earned its reputation. Jack-o-lanterns, originally turnips, were not made from pumpkins until the 1840s (although Irving benefits profoundly for having unknowingly selected the perfect vegetable to enthrone his story in Halloween ambiance).


The actual reason that Irving chose the pumpkin is because of its cultural significance as a symbol of New England: Yankees were known for adoring the versatile vegetable which grew easily in their cold, sandy soil. I always tell my students that throwing a pumpkin at a Yankee would be like throwing hunks of cheese at a Wisconsinite, hurling tea bags at a Briton, or pelting a Floridian with oranges.





Although the name is borrowed from Caterina Van Tassel, whose grave in the Burial Ground is singled out as that of the “real” Katrina, this woman – middle aged during Irving’s youth, and known 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 model for the Van Tassel Manor) and was briefly kidnapped by British soldiers during a wartime raid (before she and her female relatives fought the attackers off). Spirited, feisty, flirtatious, and beautiful, she was in her late twenties during Irving’s childhood and was familiar with both him and his family.





Brom Van Brunt was inspired by two separate men, both blacksmiths named Brom. The most notable is the war hero Abraham “Brom” Martling, who organized Tarrytown’s defenses during the Revolution. Strong, heroic, beloved, and romantic, Martling epitomized the Sleepy Hollow spirit. In his most famous adventure, he and a group of followers rowed a whaleboat from Tarrytown to the British lines in the middle of the night and burned a Tory leader's house to the ground in retaliation for the burning of the Van Tassel brothers' residence. They made it back to Patriot lines and became instant heroes for their daring act of defiance. Like Bones, Martling was the masculine ideal of the area, the local referee, the admiration of children, and the envy of men.


The other “Brom” was Kinderhook, NY's Abram Van Alstyne. According to local tradition, this Brom helped inspire the idea 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 friends' hints to pop the question to his long-suffering fiancée, Jane Van Dyck. Bothered by Merwin’s lack of initiative, mutual friends met and designed a charivari – a rustic hazing ritual meant to frighten ambling lovers into either marrying or call it quits. One night, after leaving Jane’s house, Merwin found himself being followed by a spectral horseman muffled in fluttering drapery. The stalking developed into a race, with the shapeless specter suddenly disappearing in a cackle of familiar laughter. Taking the hint, Merwin proposed and married Jane Van Dyck rather than suffer a lifetime of similar assaults.





The name “Baltus” is a throwback to the family’s Zaandam origin: Baltus was a popular name in this region because it suggested the area’s source of wealth: sawing Baltic timber for shipbuilders. While there is no precise historical model for Baltus Van Tassel, he is a conglomeration of various Dutch landowners whom Irving admired as a child. Open-hearted and open-handed, yet unwaveringly devoted to their traditions, communities, and families, these moderate entrepreneurs fascinated Irving with their easygoing natures, lack of political bile, dedication to community, and receptiveness to strangers. The closest model we have is Jacob Van Tassel, father of the spirited Eleanor and one-time owner of Wolfert’s Roost (the model of the Van Tassel Manor and later home of Washington Irving, who would transform it into Sunnyside).







A legitimate Sleepy Hollow ghost: said to haunt Raven Rock – a craggy glacial scar named for its eerie attraction of the funereal birds – this ghostly woman in white attire has two different backstories. The first is that she was a desperate single mother gathering firewood to heat her cottage before a blizzard, but that she was caught off guard and froze to death huddling under Raven Rock’s jagged walls. The other states that she was a young girl who had arranged to elope with a British officer; she arrived in her dress at the Rock on the appointed date, but he didn’t appear – instead a blizzard began to fall, but she remained steadfast to the appointment, until death overtook her. Either way, the so-called “Lady in White” moans pitiably before harsh snow storms, and has been observed in Sleepy Hollow since colonial times.





 (All military paintings by Dan Troiani)


During the Revolutionary War, Westchester County was a practical wasteland of vigilantism, wild west justice, pillaging, raids, heroics, villainy, and anarchy. Sandwiched between the Patriot lines at Peekskill and the British lines at Kingsbridge, it became referred to as “the Neutral Ground,” but was really a wild no-man’s land of lawlessness. Dozens of brutal skirmishes were recorded between Patriot and Loyalist militias, at least one full-scale battle at White Plains, and countless raids on civilians by the so-called Skinners (Patriot-allied bandits) and the Cowboys (British-allied raiders) – either of whom could switch loyalties for money. Tarrytown was raided by the British at least twice and shelled once, and a cannon was fortified just south of the Old Dutch Church to protect Philipsburg Manor from attacks by Hessian troopers (the notorious Jäger dragoons) and British light infantry. Many harrowing adventures took place in the area, including the famous 1777 raid on the Van Tassel farm (where the two Van Tassel brothers were captured by a mixed force of Hessians and Loyalists, their house burned, and their cattle stolen; meanwhile young Elizabeth Van Tassel’s daughter Leah was saved from the fire by a Hessian soldier, who also saved the two from freezing by bringing them a quilt).


 The most famous local conflict between the Crown Forces and Patriots is the Battle of White Plains. Ten miles east of Sleepy Hollow, White Plains is the county seat of Westchester, and was the site of an indecisive battle between the Continental Army (under George Washington) and the British (under William Howe) and their Hessian allies (led by Leopold von Heister). From October 27-30, 1776, the Americans held ground on and around Chatterton Hill while the Hessians charged their positions. The German battalions were mangled by a gun battery commanded by Alexander Hamilton, and were delayed when a terrible storm broke out over the battlefield. Under the cover of the tempest, the Americans retreated on Halloween night, leaving Westchester to the British, and crossing the Hudson.




 Sleepy Hollow’s most famous ghost (with a head) is the weeping figure of the dashing Major John Andre, a young, ambitious, and tremendously unlucky British spy-master who was captured outside of Tarrytown returning from a meeting with Benedict Arnold. Their plan was to surrender the Hudson River fortress at West Point to the British. In exchange, Arnold – offended at being passed up for promotions – hoped to become a British hero. Instead, the plan was discovered, Arnold fled to British lines, and the dashing John Andre was hanged as a spy. Much mourned (on both sides: Andre was handsome and accomplished, and quickly made friends with his captors), he was considered a tragic sacrifice to Arnold’s treachery (someone, after all, had to hang for it). Since his execution, Andre has been said to haunt the area of his capture. The towering tulip tree which bore his name -- about a football field's length south of Andre Brook -- was long said to be haunted by the sight and/or sound of a weeping man, and the bridge that spanned Andre Brook (now in Patriots' Park), where the militiamen captured him, is still said to be haunted. According to legend, Andre's ghost -- and sobbing -- will dissipate if you ask it "What party are you from?" -- the challenge issued to him from the American soldiers. In real life he responded truthfully that he was with the British (mistaking the Patriots for Loyalists) -- a response that his ghost still seems to regret. Like the Hessian (and later Ichabod), Andre contributes to the “legend” of Sleepy Hollow – the narrative that meddlers, invaders, mercenaries, schemers, oppressors, and raiders of all stripes will be dealt with firmly, and expelled (if not destroyed)






 The historical Sleepy Hollow is not the current village, but the valley of the Pocantico River, just east of the modern suburb. Thankfully, much of this land is currently assigned to parkland (Douglas Park and the Rockefeller State Park), where its quiet, peace, and beauty can still be appreciated. The Pocantico River – a tributary of the Tappan Zee and the black, bubbling stream that Ichabod will race to in the climax – runs northeast from the Hudson River, cutting its way between the hills that define Sleepy Hollow, splashing over boulders and fallen trees. A strange, jealous effort has been made by the town of Kinderhook, NY to argue that Sleepy Hollow never existed and that it was inspired by their sleepy upstate village. For proof they offer that Sleepy Hollow, NY was called North Tarrytown until the 1990s, that the schoolmaster Merwin and the blacksmith Brom Van Alstyne called Kinderhook home, and that Irving frequently journeyed there.


The argument is fragile at best, pathetic at the worst: not only did Sleepy Hollow exist on maps dating back to before the English took New York from the Dutch, but -- as I discuss in "The Old Albany Post Road" -- Irving laces his story liberally with actual landmarks from Andre Brook and Raven Rock to the Old Dutch Church and the "rising ground" of Sleepy Hollow High School. It is true that North Tarrytown chose to change its name and that it was never considered Sleepy Hollow, but "Sleepy Hollow" -- the peaceful valley downriver from the church -- is conveniently located a mile and a half from the center of the town which now bears its name: a quiet, shady vale made up of rolling hills, whispering trees, and monolithic boulders. 





(Map by Michael Kellermeyer)


Ichabod’s journey home lines up more or less with modern Route 9, one of the oldest highways in the country. Based on an old Indian trail, the road was later widened and served as the main artery from New York to Albany, running parallel with the Hudson. Ichabod rides home along this road after leaving the Van Tassel manor in East Irvington (Irving would later purchase the old Van Tassel homestead and renovate it into Sunnyside, the mansion where he would retire). Tracing his way north parallel to the Hudson, Ichabod would enter the shadowy woodlands that loomed on either side of the road. Two-hundred yards south of Patriot's Park, the road curved on either side of the monstrous tulip tree called Andre's Tree, before meeting again and dipping down into the tangles of Wiley’s Swamp. Ichabod would meet the Horseman here at the bridge over Andre Brook, and they would ride alongside each other in mute darkness until the road rose up the slope where the Sleepy Hollow High School currently sits. From this spot – where Ichabod sees the Horseman in stark relief against the sky – he plunges down Route 9 and attempts to turn down Bedford Road (the old Sleepy Hollow Road), but Gunpowder keeps left and leads him towards the church. From here the historic Albany Post Road made an S-shaped curve while modern Route 9 keeps going straight.


Ichabod’s flight would have taken him up Route 9 before merging onto New Broadway (the path of the Old Post Road) for a few blocks, after which it would have curved left, pounding through what is now the Webber Park Neighborhood -- parallel with modern Crane Avenue -- west towards the Pocantico, and across the bridge, just south of Douglas Park. This bridge -- already abandoned by the time Irving penned the story -- was originally positioned some 100 yards upstream of the current “Headless Horseman Bridge,” but almost half a mile downriver from the wooden replica at the northern edge of Douglas Park. From here the road would have swung west (running parallel to the river and just south of the Church), before crooking north again (completing the S-shape) and hooking up again with modern Route 9, running past the Church’s doors and north towards Ossining.   




The Van Tassel Manor is not based on one single estate, but on a combination of places. Geographically and historically, it is based on Wolfert’s Roost (later Sunnyside) in Irvington, New York, three and a half miles from the Old Dutch Church. Wolfert’s Roost was owned by Jacob Van Tassel and his daughter Eleanor, but as a stone farmhouse it doesn’t match the architectural details of Baltus’ sprawling estate. The Van Cortlandt Manor in nearby Croton-on-Hudson is the very picture of Balt’s welcoming Dutch stronghold with its yawning piazza, rolling farmland, and elegant, colonial interior. Ultimately, in Irving’s imagination, the Van Tassels live in the vicinity of Wolfert’s Roost, in a manor that resembles the Van Cortlandt property.





Referred to as Major Andre’s Tree, this historical landmark was so massive that the Albany Post Road split in two and skirted it





The gloomy haunt of the Woman in White can still be found by hikers and sightseers. Raven Rock is located in a particularly quiet part of the Nature Preserve called Buttermilk Hill. During the Revolution, locals would hide their cattle in its shadow when raiders were spotted on the trail, giving the slope its bovine name. Even today, however, Buttermilk Hill is an unsuitably pleasant name for this shadowy glen, and everyone refers to it by the name of its monstrous monolith. It is the largest glacial erratic in the country – a 600 million year old relic of the icy juggernauts that carved their way down the Hudson Valley, strewing the wild landscapes with cyclopean debris. The formation still has an unnerving, magnetic influence on travelers who are often unaccountably disturbed by its immense size and strange, house-like dimensions. It is not an irregular pile of boulders or a sloping promontory, but a flinty non sequitor – a black block of craggy granite – rising like a gloomy manor house out of the maples surrounding it.





Wiley's (or more accurately Wildey’s) Swamp (part of property once owned by Caleb Wildey) – a marshy ravine – has long since been drained, although the rivulet that fed it (now called Andre Brook) still bubbles through Patriots’ Park in Tarrytown today. Named for the three militiamen who arrested Andre and resisted his bribes, the park is also remembered as being the spot where Ichabod first encounters the Headless Horseman. Patriots’ Park is .7 miles from the Old Dutch Church where the race will ultimately conclude. The original bridge – the three rough logs – which Ichabod struggles to get Gunpowder to cross was a few dozen yards east of the stone bridge which currently spans Andre Brook, and their first encounter probably took place just east of Patriot’s Park, on the other side of Route 9.





Currently there are two bridges near the Dutch Church which span the Pocantico: the official Headless Horseman Bridge (an uninspiring multilane concrete structure just south of the church on Route 9), and a romantic wooden structure with trusses and railing made from tree branches (half a mile upriver of the boring modern bridge). Neither of these are in the spot where the original Headless Horseman bridge lay.


There have been five different bridges since colonial times, and the road itself has been moved at least three times. The bridge in the story would have been located some several hundred yards east (upriver) of the current modern structure spanning Route 9. In all likelihood, it would have spanned the river directly east of Washington Irving's grave, crossing over into the middle of Douglas Park at a deep, broad part of the river.  During the Revolutionary War a fortification was built on top of Battle Hill overlooking the Post Road and the river (only a few strides from Irving's grave), and its plausible that the cannon there was trained on the former bridge. This bridge is said to have been plain (bordering on ugly), without architectural embellishments or ornamentations. A photograph of one of the bridges which existed during Irving’s lifetime (but after the colonial structure had been dismantled) shows a sagging wooden span with a triangular support on either side.


It was never, as the Disney version popularized, a covered bridge.





The Old Dutch Church remains the second oldest church in New York, founded in 1685 by the Dutch settlers of Tarry Town. Its Old Burial Ground contains the remains of many models for Irving’s characters as well as Irving himself. Its iconic stone walls, bell tower, and peaked windows have made it a symbol of the area since colonial days. 


Atlas Obscura describes it thus: "The oldest existing church in New York, the Old Dutch Church of Sleepy Hollow (also known as the Dutch Reformed Church) and its two-and-a-half-acre colonial-era burying ground served as the inspiration for Washington Irving’s short story “The Legend of Sleepy Hollow.” Founded in 1685, the church is among the oldest in the United States and still has an active congregation. Construction began around 1682 by Frederick Philipse, lord of a huge manor in the lower Hudson Valley. His lordship built with the church two-foot-thick walls composed of local fieldstone. A carpenter by trade, he built the pulpit himself and lies buried with thirteen family members under the church floorboards.


"The Friends of the Old Dutch Church and Burying Ground, a nonprofit, all-volunteer organization, maintains and preserves the site. It was named a National Historic Landmark in 1961. Today, the church is owned by the Reformed Church of the Tarrytowns and still used for summer services and on Easter and Christmas Eve. Among the notables buried on in Sleepy Hollow Cemetery adjacent to the church’s grounds are Andrew Carnegie, Walter Chrysler, Samuel Gompers, Elizabeth Arden, Leona Helmsley, Brooke Astor, and William Rockefeller. The cemetery also holds the remains of local people who inspired Washington Irving’s “Sleepy Hollow” characters. Every autumn, tens of thousands of visitors flock to the Old Dutch Church and the Sleepy Hollow Cemetery for seasonal events that draw on the legend."


You can find our collection of Irving's best ghost stories (including the annotated, illustrated "Legend of Sleepy Hollow") HERE





"Legends and Lore of Sleepy Hollow and the Hudson Valley," by Jonathan Kruk

"Historical Sketches of the Romer, Van Tassel, and Allied Familes," by John Lockwood Romer


"The Place Names of Historic Sleepy Hollow and Tarrytown," by Henry Steiner


 (All military paintings by Dan Troiani)







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