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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.




(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’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).