The True Inspiration Behind The Legend Of Sleepy Hollow And The Infamous Headless Horseman

evgavrilov - illustrative purpose only, not the actual person
evgavrilov - illustrative purpose only, not the actual person

Each year, as soon as brisk autumn air replaces summer’s humid heat, Washington Irving’s chilling ghost story, The Legend Of Sleepy Hollow, is at the center of American folklore.

This classic tale involves a superstitious school teacher named Ichabod Crane, who happens upon a supposedly haunted town known as Sleepy Hollow, New York.

There, Ichabod is subjected to a horrifying encounter with a headless horseman who haunts the town before disappearing forever.

The legend has continued to fascinate the American public for two centuries, and the actual town of Sleepy Hollow lures tons of horror fans every year, hoping to catch a glimpse of the headless horseman.

But, this American tale drew inspiration from mythical creatures and events around the world.

The Headless Horseman

Tales of decapitated men on horseback are not unique to American culture. Instead, iterations of this legend are shared throughout parts of Northern Europe and Scandanavia.

For example, Celtic tradition speaks of a “dullahan”– a headless demon who bolts around atop a black stallion. And another tale, The Wild Hunstman by Gottfried August Burger, a German poet, featured ghostly men on horseback who dare not be encountered.

Washington Irving was well educated and even traveled throughout Europe while writing some of his earlier short stories. So, he likely would have read about these legends and perhaps drawn some inspiration for his own iteration.

evgavrilov – illustrative purpose only, not the actual person

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But, literature is not the only source to influence Irving.

The Myth Of The Hessian Soldier

After the American Revolution, a myth emerged that spoke of a headless Hessian soldier– or a German troop who aided the nation’s battle against the British.

But, this specific Hessian was tragically decapitated via cannonball during the 1776 Battle of White Plains.

And, as legend has it, the soldier’s corpse was buried in Sleepy Hollow at Old Dutch Church. Then, the Hessian was believed to rise from the grave each night in hopes of finding his head.

Even though the latter part of the story might sound fictitious, New York Historical Society records do indicate that there really was a soldier who suffered decapitation during the Battle of White Plains.

“A shot from the American cannon at this place took off the head of a Hessian artilleryman,” wrote Major General William Heath in a 1798 memoir.

Nonetheless, Irving also had another, more personal source of influence for the legend– his own life.

The True Places And People Behind The Legend

Irving originally grew up amidst the hustle and bustle of New York City. But, at fifteen, he moved upstate to a region known as Tarrytown– where a close friend, James Kirke Pauling, lived.

However, Irving did not just visit Tarrytown for a weekend getaway. Instead, he fled home because, in 1798, New York City was being ravaged by yellow fever.

At the time, though, escaping the urban setting was not feasible for all city dwellers. Irving was only able to because he hailed from a wealthy family who could afford to travel elsewhere. And the idyllic countryside region that Irving ended up in went on to inspire much of his writing. He particularly loved the Catskill Mountains and claimed they had a “witching effect” on his mind.

Plus, aside from The Legend Of Sleepy Hollow being based on a real New York town, Irving also based the legend’s characters on real people.

For example, Ichabod Crane is believed to have been inspired by Jesse Merwin. Jesse was a mutual friend of both Irving and former president Martin van Buren who taught in upstate New York and frequently kept Irvin company. Additionally, the name “Ichabod Crane” actually belonged to an army officer who served during the War of 1812. In fact, Irving and the real-life Ichabod were even stationed at the same location during the war. However, there is no conclusive evidence that the pair ever met.

Finally, Ichabod’s love interest in the legend, Katrina Van Tassel, was also supposedly based on a woman named Eleanor Van Tassel Brush– a Tarrytown resident described as “ripe and melting and rosy-cheeked as one of her father’s peaches.”

Reality Informs The Supernatural

It is clear that Irving’s famous tale is a concoction of various experiences– both lived, mythical, foreign, and personal. And perhaps that is why The Legend Of Sleepy Hollow has remained such a compelling story in horror folklore all of these years.

“It inspires people because it reminds them that there are still some American mysteries, some half-truths that may never be fully known– and that’s the whole point. The ‘legend’ lends itself to any interpretation, and it continues to fascinate and terrify us in the best possible way,” said Elizabeth Bradley, a Historic Hudson Valley historian.

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