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

M. Grant Kellermeyer
Sep 4, 2018
22 min read

Updated: Nov 21, 2023

“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 (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 for lightly armed cavalrymen 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 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 “hunter” 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 "Mounted Rangers." All Jägers wore dark green uniforms with crimson-red lapels, green vests, and leather breeches. Jägers in the dragoon company were armed 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 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 in disguise and not the ghost of a dragoon scout. 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 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 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 general action 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 this specific battle).

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). 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 raiders galloping down the road only to take a broadside from the cannon aimed at them from the wooded slope overhead. 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: his head either chewed to pulp by grapeshot or wholly "carried away" by roundshot.

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 Hessian were unceremoniously buried in the old graveyard in an unmarked plot (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 gesture of gratitude to one of his brother soldiers who had compassion on them during a family tragedy.

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.

As described by Sleepy Hollow's resident storyteller, Jonathan Kruk, in Legends and Lore of Sleepy Hollow and the Hudson River Valley, when a headless Jäger corpse was discovered on the side of the Post Road later the following spring, Elizabeth paid for its burial (Kruk pp. 117 - 118). 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, fifteen years later, the ghost of a headless Hessian dragoon was 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.

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 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 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.

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 brothers' residence (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, 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.

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 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.

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, 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 honorable partisans, 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 a May 26, 1779 assault (in which Sleepy Hollow was spared by the threat of the cannon overlooking the church birdge) and the July 3, 1782 raid 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 (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

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 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 jacket stolen from a Hessian Jäger) and two Skinners who were lurking in the thicket on the side of the road.

Seeing the instantly recognizable uniform -- forest green faced with crimson -- Andre assumed that they were friends and owned up to being British when they asked him to which "party" he belonged. 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).

See more: Kruk pp. 78 - 93

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, the majority of this land is mainted 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.

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 present-day road, 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. 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. Patriots’ Park is 1,300 yards (.7 miles) from the Old Bridge where the race will ultimately conclude. 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. The crumbling stone foundations of the original, colonial-era bridge can still be seen today at a bend in the creek within sight of Washington Irving's grave (see above photo, with arrow pointing to the old foundation).

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 the field gun installed there was trained on the former bridge and the road leading to it. 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 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

See more: Kruk p. 99

THE OLD DUTCH CHURCH AND BURIAL GROUND:

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."

See more: Steiner pp. 90 - 92