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The Truth Behind the Legend: Historical Inspirations for Irving's Horseman-Haunted Sleepy Hollow


“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 still shades of the Rockefeller State Preserve, the gloom of Raven Rock, and the rolling hills of the Old Albany Post Road speak to the story's authenticity. When you read "The Legend of Sleepy Hollow" it feels oddly true -- there is no better word for it -- grounded in a reality of place, culture, and history, and for good reason. While the tale of a comical schemer scared straight by a goblin rider 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 setting, details, and characters are faithfully shaped out of post-Revolutionary Westchester County.


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 local details of the actual Headless Horseman (including his military context), the two still-standing 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.

CHARACTER INSPIRATIONS

THE HEADLESS HORSEMAN

AND THE "NAMELESS BATTLE":

(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 weak, 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 their sleeping garrison was overwhelmed in an early morning raid that turned the tide of the war). 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 (although in reality, the prince -- not the soldiers -- pocketed King George's cash).

The Headless Horseman is only described as a "Hessian trooper" -- a mounted soldier. The Hessian forces had several units of light dragoons who frequently scoured the chaotic no-man's land of Westchester County, including rebel-infested Sleepy Hollow. These dragoons were part of the Jäger Corps (pronounced “YAY-gur,” meaning “huntsman” or “ranger”). Rangers wore dark green uniforms with apple-red lapels, green vests, and leather breeches with tall, black boots. Rangers in the dragoon unit were armed with a curved 33 inch-long steel saber weighing just under three pounds, a brace of pistols, and a carbine flintlock rifle.

The Headless Horseman is usually depicted in a fluttering black or scarlet cape, but this, more than anything else, suggests that the rider who chases Ichabod is Brom in disguise and not the ghost of a dragoon. Dragoons on patrol were very unlikely to wear capes or cloaks, which restricted movement, became entangled in trees and brush, and were too clumsy for these high energy scouts. Instead of a cape, the Horseman would most likely have either worn an overcoat or buttoned up his heavy, wool uniform jacket to keep out the cold or rain.

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, aggression, and horsemanship.

We know virtually nothing about how the Horseman died. Irving only notes that his "head was carried away by a cannonball during some nameless battle." There has been a spirited campaign by some commentators who 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.


One oft-cited report from the battle tells of a Hessian artilleryman who was decapitated by one of Alexander Hamilton’s cannon, and this is certainly interesting, but Irving likely means exactly what he says, and since he later refers to the “Battle of Whiteplains,” I hardly think he imagines this 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 British and Hessian raiders from time to time. My own inference 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 tense few minutes of action, the raiders retreat back down the old Post Road, leaving behind a mutilated comrade. What could be done other than get the headless corpse out of the road? Where better to dispose of it 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. On the brutally cold night of November 17, 1777, a raiding party of Hessian and Tory dragoons under Captain Andreas Emmerick 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 raiding 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 headless Jäger corpse was discovered on the side of the Post Road later the following 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.

ICHABOD CRANE:

Ichabod 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 had a very specific historical significance in post-Revolutionary New York. Enterprising 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 this skill, since it is his unspoken desire -- once he hypothetically marries Katrina -- to liquidate her economy-driving estate, and move to Kentucky to set up his fortune: the late 18th century equivalent of buying a factory and sending its jobs overseas.

In fact, Brom's choice of weapon -- the humble pumpkin -- is a frequently overlooked regional allusion to Ichabod's status as a New England prospector. While we see it as being used because it is a Halloween trope, the pumpkin was actually intended to be a piece of regional rhetoric, urging the pumpkin-chomping Yankee to go back whence he came. Today we imagine the Headless Horseman flinging a flaming jack-o-lantern with its terrifying face of fire: this is only because Irving massively lucked out by picking the ultimate spooky vegetable, a full twenty years before it became associated with Halloween: Jack-o-lanterns, originally made from large turnips, were not made from pumpkins until the 1840s.

The actual reason that Irving chose to arm the Headless Horseman with a pumpkin is because of its cultural significance as a symbol of New England: Yankees were known for adoring this versatile vegetable which grew easily in their cold, sandy soil. I always tell my English students that throwing a pumpkin at a New Englander would have been like throwing hunks of cheese at a Wisconsinite, hurling tea bags at an Englishman, or pelting a Floridian with oranges: the message -- to go back to where you came from -- would be clear.

KATRINA VAN TASSEL:

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 Caterina's niece, Eleanor Van Tassel. 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 "BONES" VAN BRUNT:

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 1777 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 calling 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.

BALTUS VAN TASSEL:

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).

LOCAL TALES AND TWILIGHT SUPERSTITIONS

THE GHOST OF THE WOMAN IN WHITE:

A legitimate Sleepy Hollow ghost: said to haunt Raven Rock – a craggy glacial scar named for its eerie tendency to attract these gloomy birds – the ghostly Woman in White 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.

SLEEPY HOLLOW DURING

THE REVOLUTIONARY WAR:

(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 two violent gangs of mounted bandits: the Skinners and the Cowboys. While the Cowboys were overtly Tory partisans, the Skinners were truly frightening criminals could switch loyalties for money.


Tarrytown was raided by the British at least twice (July 3, 1782 and ), occupied once (October 5, 1777) was the site of the Battle of Young's Corner (February 3, 1780), was used as George Washington's headquarters several times (he is known to have stayed at both Couvenhoven Inn and Hammond House), and was shelled by the Royal Navy once (July 15, 1781), and a cannon was fortified just south of the Old Dutch Church to protect Philipsburg Manor from attacks by Hessian dragoons (specifically, Captain Andreas Emmerick's notorious Jägers), Cowboy gangsters, and Loyalist raiding parties.


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 Elizabeth Van Tassel and her daughter, Leah, were saved from freezing to death by a warm-hearted Hessian dragoon).

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 Washington's Continental Army -- holding the high ground south of town -- and Sir William Howe's British army (supported by General Leopold von Heister's Hessian auxiliaries) invading from the Bronx River Valley below.


From October 27-30, 1776, the Americans held ground on and around Chatterton Hill while waves of Hessians charged their positions, supported by the Royal Artillery Corps. The German battalions were mangled and stalled by a Patriot cannon battery (commanded by Colonel Alexander Hamilton), which delayed their advance until a terrible storm broke out over the battlefield, drenching both sides and blackening the sky. Under the cover of the tempest, the Americans retreated on Halloween night, leaving Westchester to the British, and crossing the Hudson to survive another day.

THE GHOST OF THE

"UNFORTUNATE" MAJOR ANDRÉ:

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 just outside of Tarrytown returning from a meeting with Benedict Arnold. Their plan was to weaken the Hudson River fortress at West Point, and hand it over to the British (which would have alienated New England and likely ended the war). In exchange, Arnold – offended at being passed up for promotions – hoped to become a British hero. As he prepared to cross the creek in Wiley's Swamp, he was jumped by an escaped American prisoner (dressed in a stolen Hessian jacket) and two Skinners who were lurking in the thicket on the side of the road.


Seeing the green coat, Andre assumed that they were Tories and owned up to being British when they asked him which party he belonged to. They immediately began searching him and found the plans to West Point in his boot. Andre tried to bribe them, but realizing that he was more valuable as a prisoner than any cash he might have on him, they took him to the Patriot authorities, and the jig was up. When he heard that his handler had been captured, Arnold fled to British lines, and the dashing John Andre was hanged as a spy.


Much mourned (on both sides: Andre was extremely likeable and quickly made friends with his own 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 100 yards south of Andre Brook -- was long said to be haunted by the sight or sound of a weeping man, and the bridge that spanned Andre Brook (which now runs through Patriots' Park), where the militiamen captured him, is still said to be haunted.


According to legend, Andre's sobbing ghost will only 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)

LANDMARKS

SLEEPY HOLLOW AND THE "HAUNTED BROOK":

The historical Sleepy Hollow was not a village, but the whole valley of the Pocantico River, just east and upriver of the modern suburb. Thankfully, much of this land is currently assigned to protected parkland (Douglas Park and the Rockefeller State Park), where its quiet 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 1996, and 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 all the way back to 1655, but -- as I discuss in "Ichabod's Ride" -- Irving floods his story with Tarrytown landmarks (e.g., Andre Brook, Wiley's Swamp, Raven Rock, the Old Dutch Church, Andre's Tree, etc.).


It is true that North Tarrytown chose to change its name and that it was never considered Sleepy Hollow per se, but "Sleepy Hollow" -- the peaceful valley upriver from the church -- is still 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.