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

M. Grant Kellermeyer
Sep 4, 2018
34 min read

Updated: 3 days ago

“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 (cf. 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

&

THE "NAMELESS BATTLE":

(The above painting by military historian Don Troiani actually depicts a Hessian patrol of Jäger scouts -- including a mounted dragoon -- in Sleepy Hollow: they are crossing the bridge over the Philipsburg Manor Mill Pond, just across from the Old Dutch Church, near

the modern Headless Horseman statue.)

"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 and Fort Washington (where they terrified the Americans with their skill and ferocity), Bennington (where they were slaughtered by vengeful militiamen), and Trenton (where their exhausted 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. Like the Americans and French, the British and Hessians had no heavy cavalry in North America, only dragoons, chasseurs, and hussars: three terms (with no significant difference in meaning) for lightly armed horsemen trained and armed to fight either on horseback or one foot, who served primarily as scouts, shock troops, and raiders. Dragoons needed to be athletic, intelligent, and stealthy, and every army in the Revolutionary War employed units of these fearsome horsemen.

The Hessian forces had only one company of light dragoons who frequently scoured the chaotic no-man's land of Westchester County (including rebel-infested Sleepy Hollow) -- but these troopers were thoroughly used and widely feared. They belonged to the larger Jäger Corps (pronounced “YAY-gur,” meaning “huntsman” or “ranger”).

Jägers were feared scouts -- skilled light infantrymen trained in skirmishing, raiding, reconnaisance, and foraging -- recognizable for their dark green uniforms and short rifles (they were among the very few Crown troops armed with rifled guns). Jägers were recruited from the Prince of Hesse-Kassell's own foresters and game-keepers, and were required to be "good shots, agile, intelligent, and self-reliant." As such, they were well-suited to fighting in the American forests and were a formidable match to the Yankee riflemen.

Most Jägers -- five of the six companies -- were infantrymen, but one company of 100-some men and 20-plus officers were called the Jäger zu Pferd Kompanie: literally, the "Hunters on Horseback" or, colloquially, "Mounted Rangers." All Jägers wore dark green uniforms with crimson-red lapels, green vests, and leather breeches. Jägers in the light dragoon company were armed differently, however, with a curved 33 inch-long steel saber, a brace of pistols, and a carbine rifle and wore tall black boots instead of green, canvas gaiters.

The dragoons were "recruited primarily from the service of professional hussars and cavalrymen; a breed of men who by the very nature of their previous service were reckless and daring," and one researcher remembered them as "really tough buggers [who] drew many complaints from the rebels who were roughly handled by them. These were 'the fellows who wore the boots.'"

The Headless Horseman (following Ichabod's observation of a lumpy-looking figure suspiciously "muffled in a cloak") is usually depicted in a fluttering black or scarlet cape, but this, more than anything else, reinforces the idea that the rider who chases Ichabod is Brom wrapped up in a disguise and not the ghost of a dragoon scout.

Dragoons on patrol would never have worn 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. They were led by a captain -- not a colonel or general -- who would have looked pretentious and irresponsible sauntering about in a cloak used as a sign of rank.

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 the action in which 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 unequivocably the Battle of White Plains fought ten miles away from Sleepy Hollow just one day before Halloween in 1776.

One oft-cited report from the battle tells of a Hessian artilleryman who was decapitated by one of Alexander Hamilton’s cannons, and while this is certainly interesting, Irving likely means exactly what he says, and since he later specifically refers to the “Battle of Whiteplains,” I hardly think he imagines this well-known general action between Washington and Howe themselves, involving ten thousand combatants, and resulting in 500 casualties to be a "nameless" footnote in history (nor would the braggadocious veterans at Van Tassel's party who loved describing their roles in this specific battle).

However, there is a much more interesting a realistic solution to the problem of where the battle took place.

During the war a small cannon was installed and fortified on the churchyard's southern slope (today called Battle Hill) guarding the famous church bridge and the Albany Post Road (modern Route 9). The earthwork redbout gazed down at the bridge and the road, and was manned by Patriot militiamen from 1778 on. The gun (or pair of guns) there was certainly no larger than a six-pounder (maybe even as slight as a four-pounder), but the little fortification seems to have been effective.

Although no pitched battle ever took place under its watch, it was used to frighten off British and Hessian raiders from time to time. At least one skirmish is recorded where a hurry-scurry squadron of Cowboy raiders was immediately scattered following a single discharge from the field piece trained on the bridge.

My own inference is that Irving intends us to imagine a similar situation. Using a heaping spoonful of creative license, I would envision this action as involving a squad of Jäger raiders galloping down the road, trying to make the bridge before they're noticed, only to take a broadside from the cannon aimed at them from the wooded slope overhead. The round crashes into the woods behind them, and they spur their horses all the faster: if they can but reach the bridge and gain the opposite side, soon they'll be too close to the slope for the gun to bear on them and they can blaze past the church in safety to complete their mission.

But the cannoneers have reloaded and recalibrated their aim, and before they gain the planks, the second shot sends a six-pound ball barrelling right in their midst (some feel its heat as it passes over their shoulders). There is a spray of maroon mist and a thump as the rider at their head is dragged backwards off of his horse by the momentum of the 3.5-inch wide iron ball that just vaporized his head.

Maybe some frustrated pistol shots are fired back at the gunners, but before the militia can swab the gun a third time, the patrol whirls around -- horses whinying, scabards clattering -- but the raiders turn tail and thunder back down the Post Road amid snarls of "Zum Teufel!" and "Potz Blitz!" As the breeze blows away the creamy blackpowder smoke, all are gone except for the one left behind in the melee.

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? (Again, this is all picture painting on my part; we have no such records of a Hessian horseman being decapitated like this).

It is, however, reasonable to speculate that if any Hessian soldier was actually killed, specifically, by cannon-fire in the vicinity of the Church – close enough to be buried there instead of in situ – that he would have been hit by a round from Battle Hill, and if he was shot down from the field piece trained the bridge, it is natural to suppose that the stretch of road before the crossing was also the site of his demise.

This is intriguing, if for no other reason, than in the literary parallelism: the Horseman is known for racing towards the bridge but disappearing in a blaze of sulfurous fire and a cannonade of thunder and lightning before he can make it, almost as though he is stuck in a loop reliving his explosive death at the crossing. More casual speculation, though, so let us get back to what we do know or what little, at least, traditions have told us about a Hessian body in the Old Dutch Burial Ground.

Whether or not there is a Hessian of any variety buried in the old churchyard is impossible to confirm. Oral traditions suggest "possibly yes," but we simply don't know and there is not even a single stroke of the pen written about a Headless Horseman or a buried German that predates Irving's tale. This doesn't mean that he invented the folklore (there are no writings from locals that describe it as his invention or complain about reckless myth-making), but we truly have no evidence in either direction until probably the 20th century.

However, there is the following tradition connected to an excessively documented wartime atrocity, which has been reverted to by such local luminaries as late sexton of the Old Dutch Church and amateur historian William "Bill" Lent and Jonathan Kruk as a potential link between historical events and a headless hessian.

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 cousins 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.

Elizabeth was tied up outside while her furniture was being stolen, her house aflame, and her baby girl left inside. It was about to become an incredibly dark episode of the Neutral Ground, when, hearing Elizabeth's frantic pleas, one dragoon rushed inside and wasn't seen for awhile. To Elizabeth's relief, he reemerged with the baby in his arms before the house caved in. Once they were reunited, he saved the pair (a second time) from freezing by recovering a quilt, feather mattress, and bedding for them to keep warm in before rejoining the raiders on their march back to New York.

Both cousins, Elizabeth, and Leah would be reunited and survive the war (though, sadly, their teenage son, Cornelius Jr., died three years later from an illness he incurred from exposure during the attack). But the story doesn’t end there – at least according to some.

As energetically relayed by Kruk and Lent (sexton of the Old Dutch Church and a collector of oral traditions) there is a tradition – unattested to by any primary sources, though its claims are not at all outlandish – that, a year or two after the Van Tassel Raid, the corpse of a decapitated Jäger was discovered in the mud of the Albany Post Road near the Church.

Reminded of the kindness shown to her family by his countryman on that terrible November night, Elizabeth Van Tassel is said to have paid for this unknown soldier’s burial in the churchyard (Kruk pp. 117 - 118). His unmarked grave, according to local lore, can still be identified today, and was one of Lent’s most famous stops during his graveyard tours before his death in 2013. The conspicuously empty patch of ground can be seen when facing Caterina Van Tassel's gravestone "l ooking towards the east boundary of the churchyard -- just above where the old bridge crossed the Pocantico River."

(Photo taken during a tour with Lent, showing the spot he indicated where the Hessian is reported to have been buried according to oral tradition)

Whether the dead German was a foot soldier or a dragoon isn't recorded, but we do know that by the time Washington Irving was a young boy, some fifteen years later, he claims to have heard stories about the ghost of a headless Hessian dragoon in Sleepy Hollow.

While there is absolutely no extant record of authenticated folklore prior to 1820 attesting to a local belief in a Headless Horseman, Irving claims that the goblin rider 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, two miles upriver from the Dutch Church, in the silent heart of Sleepy Hollow) and credits this nameless folklorist with many of his childhood nightmares.

For more details on the Hessian Jäger Corps during the campaigns of '76 and '77, read this excellent article from the Journal of the American Revolution and this reenactor page on the Jäger company of dragoons.

See more: Jonathan Kruk pp. 111 - 118

ICHABOD CRANE:

Ichabod Crane’s physical appearance is borrowed from Lockie Longlegs – a Scottish teacher whom Irving wrote about cheerfully to Sir 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, and quicly earned Dutch settlers' contempt as trecherous schemers. 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.

During the 18th century, New Englanders were called "pompkin [sic] heads" or "pumpkin-growers" and the Bay State was derisively called "Pompkinshire" and the "Pumpkin Dominion" by their trading rivals. 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.

See more: Kruk pp. 105 - 109

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 affectionately nicknamed Laney. S he became a local legend in her own right during a British raid on Wolfert's Roost while her father was away. A British naval landing party plundered the home and attempted to kidnap the young, attractive Eleanor.

In response, Laney, her mother, her aunt, and a family servant armed themselves with household items and fiercely fought off the soldiers, forcing a disorderly retreat and securing her release. Spirited, feisty, flirtatious, and beautiful, she was in her late twenties during Irving’s childhood and was familiar with both him and his family.

See more: Kruk pp. 103 - 104

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 two whaleboats from Tarrytown to the British lines (pp. 96 - 98) 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 cousins' residences (pp. 46 - 48). 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, N.Y.'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.

Finally, the surname "Van Brunt" came from an influential Dutch family -- magistrates, landowners, and patriots -- who settled in the Brooklyn neighborhoods of New Utrecht and Gravesend. In the snug world of 18th century New York, this family would have been well-known to the Irvings living in the Manhattan financial district just across the East River.

This just continues Irving's trend of stitching local lore, geography, history, and family names into his "Legend." (My thanks to history buff, geneologist, and "Sleepy Hollow" fan, Valerie, for pointing this out!)

See more: Kruk pp. 101 - 103

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).

See more: Kruk pp. 96 - 98

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 three different backstories. The most famous and least sensational has it that:

“A woman, so we have read, wandered out of the path of a blinding snowstorm and sought shelter from the blast of the wind in the ravine behind Raven Rock. The snow drifted in upon her and she went to sleep never to waken again. Ever since, that cleft has been a melancholy place of refuge, for it is said that the spirit of the poor wayfarer meets the belated wanderer with cries that sound like the screaming of the wind, and gestures that remind one of the sweep of snowdrifts, warning others away from the spot that she found so fatal.”

Another claims that she was a desperate Indian maiden who committed suicide by jumping from its top while running away from a would-be rapist. A slightly different version of this same story describes the victim as a Patriot-affiliated local beauty who was being persued by a lustful Loyalist before she jumped to her death. Some versions of this feature a murder rather than a suicide. Both stories are attested to by folklorist Edgar Mayhew Bacon in his Chronicles of Tarrytown and Sleepy Hollow as early as 1897.

A fourth rendition, shared by Jonathan Kruk, states that she was a young girl who had arranged to elope with a British soldier; she arrived in her dress at the Rock on the appointed date, but he didn’t appear – instead a blizzard began to fall. Undaunted and trusting in her beau, she remained steadfast to the appointment, until the snow and death overtook her.

Either way, the so-called “Lady in White” is said to be heard moaning pitiably before harsh snow storms, and has been observed by Sleepy Hollow locals since at least the late 18th century.

See more: Kruk pp. 67 - 75

See more: Henry Steiner pp. 112 - 113

SLEEPY HOLLOW DURING

THE REVOLUTIONARY WAR:

(These paintings by military historian Dan Troiani depict Jäger dragoons in action: on patrol in the first, and in action near Sleepy Hollow in the second, which

depicts the bloody Battle of Edgar's Lane,

a skirmish on the Albany Post Road,

just seven miles south of the bridge)

During the Revolutionary War, Sleepy Hollow's 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 both parties were ostensibly partisans devoted to their respective causes who waged war as humanely as circumstances could permit, some were truly frightening vigalantes who were known to switch loyalties for profit and delighted in revenge with mafia-like creativity and relish.

Tarrytown was raided by the British multiple times, including: the Decmber 1778 raid at Young's Corner

a May 26, 1779 assault by Cowboy raiders who were repelled by the firing of the gun on Battle Hill, a naval engagment outside the harbor on August 4, 1776, a repulsed amphibious invasion of the port on July 15, 1781, and the July 3, 1782 skirmish where the American Mulan, Deborah Sampson, was wounded and her gender discovered.

It was 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). Of course, all this violent activity led to the fortification of a Patriot cannon just south of the Old Dutch Church (Steiner p. 20), which was used to protect the famous bridge and Philipsburg Manor from attacks by Hessian dragoons, Cowboy gangsters, and Loyalist raiding parties.

See more: Steiner pp. 19 - 20

Westchester County during the American Revolution, 1775-1783, by Otto Hufeland

Westchester County in the American Revolution: Neutral Ground, by Steven Paul DeVillo

Many harrowing adventures took place in the area, including the famous November 17, 1777 raid on the Van Tassel farm – where the two Van Tassel cousins, prominent Whig leaders and militia officers Peter and Cornelius – were captured by a mixed force of Hessians and Loyalists, their house burned, and their cattle stolen.

The two men were marched back to New York barefoot in the freezing sleet and tied to their own horses' tails and made to drive their own cattle back behind British lines. Meanwhile Cornelius' wife, Elizabeth Van Tassel and her infant daughter, Leah, were saved from freezing to death by the warm-hearted Hessian dragoon referred to above.

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. The dashing André was tasked with managing the defection of American war hero General Benedict Arnold (the new husband of one of his past Loyalist lovers – the beautiful and affluent Peggy Shippen).

Jaded because of being passed over for promotions, Arnold allowed his wife to arrange a contact with André, who sold him on handing over the Hudson River bastion of West Point in exchange for money and career advancement. Their plan was to weaken the fortress, and hand it over to the British (which would have alienated New England and likely ended the war).

Andre – a handsome and romantic socialite, poet, artist, party-planner, and man-about-town cosmopolitan turned spymaster – had been dropped off by a British warship, but the ship had been shelled by American gunners and was forced to abandon him. Arnold recommended he travel south by the country roads in civilian attire.

On the morning of September 23, 1780, he made his way back to safety escorted by one of his Loyalist spies as far as the Croton River. The flamboyant young officer was now on his own. Armed with a pass from Arnold (in case he was stopped by rebel pickets), he hoped to first be intercepted by one of the many Hessian, Loyalist, or Cowboy patrols scouring the Neutral Ground, and thus afforded a safe escort back to British lines with the plans for West Point hidden in his stocking.

Disobeying Arnold's advice, he left the country lanes and began progressing southward down the main Albany Post Road, where he would certainly expect to encounter Cowboys (or Skinners). He passed the Old Dutch Church, rounded the shadowy cemetery, and plodded over the Pocantico Bridge before heading down into the gloom of Wildey's (or as Irving spells it, "Wiley's") Swamp, a shaded, tangled ravine dominated by thick alder, willow, and swamp oak growth, where visibility collapsed to a few yards. This tight, wooded marsh-glen featured a narrow brook-crossing choke point and heavy vine cover that made it, as Irving notes, uniquely dark and claustrophobic.

As he prepared to cross the rickety bridge over Clark's Kill Brook, he was surprised by John Paulding, a recently-escaped American P.O.W. (dressed in a faded-green jacket he had taken from a Hessian Jäger), and two un-uniformed Patriot militiamen (Isaac Van Wart and David Williams) who were on picket duty, lurking in the thicket on the side of the road.

(Robert Van Nutt's depiction of Ichabod at the

Andre Brook bridge in Wiley's Swamp)

Seeing the instantly recognizable uniform -- forest green faced with crimson -- Andre assumed that they were Loyalists and cheerfully quipped that he hoped they belonged to "our party." When suspiciously questioned as to which party he meant, he quickly specified the "Lower," or British, side.

Their distinctly unpleasant reaction to this caused him to back-track (he claimed to be a Patriot spy who had been fooled by the Hessian coat into thinking they were Loyalists), but it was too late. Even showing them Arnold's signed pass for him wasn't enough to dissaude them from taking him into custody.

(After being drained and cleared, Wiley's Swamp was cultivated into Patriot's Park, named after the three militiamen who refused Andre's bribe and turned him in. This is a shot of Andre Brook)

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.

(Arthur Rackham's depiction of Andre's Tree)

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).

See more: Kruk pp. 78 - 93

The Gentleman Spy: The True Story of the British Officer who might have prevented the American Revolution by Adele Gutman Nathan

Washington's Spies: The Story of America's First Spy Ring by Alexander Rose

LANDMARKS

SLEEPY HOLLOW AND THE "HAUNTED BROOK":

THE HISTORICAL SLEEPY HOLLOW (1):

NEW NETHERLAND, TARRYTOWN,

AND THE PHILIPSE FAMILY

Much of Irving’s landscape remains surprisingly accessible today in Irvington, Sleepy Hollow, and Tarrytown. Part of the tale’s enduring appeal also lies in its remarkable historicity. The communities now known as Sleepy Hollow (“Slapershaven” -- lit., Sleeper's Haven), Tarrytown ("Terwe Dorp" -- lit., Wheat Town), and Philipsburg Manor emerged from the Dutch colonization of the Hudson Valley during the seventeenth century.

Following Henry Hudson's voyage of 1609, Dutch settlers established farms and trading posts along the river, gradually expanding into the fertile lands east of the Hudson. In 1693, the English-born merchant Frederick Philipse, one of the wealthiest men in colonial North America, received a royal charter creating the vast Manor of Philipsburgh, a semi-feudal estate stretching across much of present-day southern Westchester County.

Tenant farmers—most of Dutch descent—worked the manor's fields, while the gristmill and trading complex at Philipsburg Manor became important centers of commerce (both were located across the Albany Post Road from the Church where it used the Pocantico to feed a millpond; both manor and mill can be visited and explored today).

Nearby, the small Dutch farming settlement of Slapershaven (named after the sheltered mouth of the Pocantico on the Tappan Zee) grew around the Old Dutch Church, completed in 1697, while the neighboring port-town of Tarrytown developed as a modest river landing and agricultural community. Together these settlements preserved a distinctly Dutch character through their language, architecture, religious traditions, and folklore long after the English conquest of New Netherland in 1664.

(Philipsburg Manor and Mill located across Route 9

from the Old Dutch Church -- and depicted in

the earlier painting by Dan Trioani of the

Hessian dragoon and light infantry)

By the eighteenth century, the region had become a prosperous patchwork of farms, mills, taverns, and river commerce, yet it remained deeply rooted in its Dutch heritage. The manor's tenant system bound many families to the Philipse estate, while the Old Dutch Church served as the spiritual and social center of the surrounding countryside.

During the years leading to the American Revolution, however, political loyalties divided the population. The Philipse family remained firmly Loyalist, supporting the Crown, while many local farmers and tradesmen increasingly favored the Patriot cause.

When war erupted in 1775, the Hudson Highlands and lower Westchester became a strategic frontier between British-held New York City and American-controlled territory to the north. The villagers and farmers in Sleepy Hollow, Tarrytown, and Philipsburgh Manor found themselves on the edge of the notorious Neutral Ground, a lawless zone plagued by raids, military patrols, and partisan violence.

Following the Revolution, the vast Philipse estate was confiscated by the state of New York for the family's Loyalist allegiance, ending the manor system and opening much of the land to private ownership, while the old Dutch settlements evolved into the communities immortalized decades later in Irving’s writings.

The original Sleepy Hollow is a very real place, though it isn’t the village of the same name north of Tarrytown, which was part of Philipsburg Manor. Just as it was in 1790 and 1820, Sleepy Hollow is the name for a geographic feature rather than a town – namely, the wooded Pocantico River Valley. Thankfully, the majority of this land is maintained as protected parkland (between Douglas Park and the Rockefeller State Park Preserve), where its quiet beauty can still be appreciated. The Pocantico River – a tributary of the Tappan Zee and the same black, bubbling stream that Ichabod must cross 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.

The valley is a glacially sculpted drainage basin in western Westchester County. The Pocantico River itself is small—only about 9 miles long—but it threads through a surprisingly dramatic terrain of rolling glacial hills and knolls, steep little wooded ravines, open meadows and pasture-like clearings wetlands, ponds, and slow creek bends.

Inside the Rockefeller Preserve, the river doesn’t feel like a “river” so much as a moving spine of water weaving through forested folds. In places it’s brook-like and intimate; in others it opens into marshy flats or reflective ponds like Swan Lake.

A strange, jealous effort has been made by the town of Kinderhook, NY to argue that such a place as Sleepy Hollow never existed and that it was entirely inspired by their sleepy upstate village. For proof, they offer that Sleepy Hollow, NY was called North Tarrytown until 1996, 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 to that of the adjacent river valley, 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.

See more: Steiner pp. 121 - 124

ICHABOD'S RIDE

(THE OLD ALBANY POST ROAD):

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).

See more: Steiner pp. 8 - 10

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 (which was located 100 yards east of the Andre Captors' Monument at the Broadway entrance to Patriots' Park, near the front doors of the John Paulding elementary school), and they would ride alongside each other in mute darkness until the road rose up and over the large, sloping hill where the Sleepy Hollow High School currently sits.

See more: Steiner pp. 13 - 17; 153

From this spot – where Ichabod sees the Horseman in stark relief against the sky – he plunges down the Post Road (which dips over the "rising ground" and runs north, past the west-side of the modern Korean Church, facing Route 9) and attempts to turn down Bedford Road (the old Sleepy Hollow Road), towards the safety of Hans Van Ripper's homestead.

However, Gunpowder keeps straight and leads him towards the Old Dutch Church. From here the colonial-era Albany Post Road followed modern New Broadway, before veering left -- near modern Crane Avenue -- and charging towards the Pocantico. The road would have finally crossed the river 100 yards northeast of the modern bridge, behind rather than in front of the Old Dutch Church.

While we don't know where the bridge was exactly, we can estimate that it was likely in line with modern Holland Avenue (likely between 18 and 38 Dell Street). From here it would continue to run parallel with the stream, passing the Church on its south side, before reconnecting with modern Route 9, and making a sharp turn northward.

See more: Steiner pp. 8 - 10; 125 -127

See more: Kruk pp. 98 - 101

THE VAN TASSEL MANOR:

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 south of 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.

See more: Kruk pp. 97 - 98

MAJOR ANDRÉ'S HAUNTED

"TREE OF THE DEAD":

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 American Citizen newspaper of August 25, 1801, reported that the tree was destroyed by lightning on Saturday, July 21, 1801. It measured 29 feet around at the base, 111 feet in height, 106 feet in diameter at the crown. Some local folk preserved pieces of the tree as keepsakes. The newspaper also recorded that the lightening strike was said to have occurred on the day that news of Benedict Arnold’s death in England arrived at Tarrytown."

See more: Kruk pp. 91 - 92

See more: Steiner pp. 14 - 17

"THE HAUNTED GLEN AT RAVEN ROCK":

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 most sources refer 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.

See more: Steiner pp. 29; 112 - 113

See more: Kruk pp. 70 - 74

WILEY'S SWAMP

(ICHABOD MEETS THE HORSEMAN):

Wiley's Swamp (or more accurately Wildey’s Swamp: it was part of property once owned by Caleb Wildey) – once 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 Patriots who arrested Andre and resisted his bribes, the park is also remembered as being the spot where Ichabod first encounters the Headless Horseman. When adjusted to account for the estimated location of the old road (Broadway to New Broadway, turn left at Crane Avenue, ending at the river across from Holland Avenue) the old Clark Kill span was about 1,300 yards (.7 miles) from the old Pocantico crossing where the race will ultimately conclude.

When imagining a hardscrabble race through stony, hilly, wooded terrain between an two horses (one a seasoned racer, one a panicked old firebrand), the race from the high rising ground to the bridge (.6 miles) would have only taken between one and three minutes depending on the terrain.

The original bridge – the "three rough logs" which Ichabod struggles to get Gunpowder to cross – was a 100 yards east of the stone bridge which currently spans Andre Brook, and their first encounter would have taken place just east of Patriot’s Park, on the other side of Route 9.

See more: Steiner pp. 13 - 14; 153

See more: Kruk p. 99

THE THREE HEADLESS HORSEMAN BRIDGES:

Currently there are two bridges near the Old 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 at least five different bridges since colonial times, and the road itself has been completely moved at least three times. The bridge in the story would have been located about 100 yards east (upstream) of the current modern structure spanning Route 9, roughly in line with Holland Avenue.

Steiner and other sources note that the crumbling stone foundations of the original, colonial-era bridge were still able to be seen as recently as 1997 at a bend in the creek within sight of Washington Irving's grave (see above photo, with arrow pointing to evidence the old abuttments). The Sleepy Hollow Country website disputes this, but this may reflect the current state of the stone remains, which may have been gradually covered up or even removed since Steiner's observation.

To defend the surrounding settlements from the frequent (and often extremely violent) incursions of Loyalist and Hessian raiders up the Albany Post Road, the main land artery between New York and Albany, a rustic fort (really a simple earthwork redoubt or lunette) was raised in 1779 on a high ridge a few hundred feet northeast of the Old Dutch Church overlooking and trained down on the colonial-era bridge.

This high ground was armed with at least one cannon, probably a small field piece, a 4- or 6-pounder. The old redoubt which overlooked the site of the colonial bridge is now gone, like the bridge itself, but the brow where it once was is now called “Battle Hill.” No known battle is recorded to have occurred there, but history (and the name) strongly suggests that several skirmishes happened there and we know for certain that the cannon was fired in anger at least once at a raiding party of Cowboys.

The bridge in question 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 and the road moved 200 yards to the southwest) shows a sagging, wooden span with a triangular support on either side.

A 19th century illustration by T. A. Richards (posted below here) shows one of the most accurate interpretations of the bridge: a plain, low span with a flimsy handrail and no other architectural details.

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

See more: Steiner pp. 8 - 10; 125 - 127