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What Is the True Story of the Real Headless Horseman?

The Headless Horseman myth is rooted in history
The Headless Horseman myth is rooted in history

An image that is called up nearly every October is that of the Headless Horseman. You might be looking for a Headless Horseman Roblox or even remember the 1999 movie Sleepy Hallow featuring Christina Ricci. You might believe that these cultural references are based on the 1820 short story “The Legend of Sleepy Hollow” by American writer Washington Irving. It is one of 34 short works Irving published in the collection called The Sketch Book of Geoffrey Crayon, Gent. (Fun fact: “Rip Van Winkle” was part of this collection!)

“The Legend of Sleepy Hollow” tells the tale of the fictionalized settlement called Sleepy Hallow which is a Dutch settlement in New York. Sleepy Hallow is a real place where Irving spent time in his youth. With a name like that, it is no wonder that its inhabitants believe the area to be bewitched or haunted and many of them have experienced their own supernatural events such as strange sights and sounds. But the most famous of these sights is the Headless Horseman. In the short story, we follow stranger-to-town Ichabod Crane through courtship and confrontation with the horseman.

But who is the real Headless Horseman?

In the story, Irving makes sure to include the following:

“… said by some to be the ghost of a Hessian trooper, whose head had been carried away by a cannon-ball, in some nameless battle during the Revolutionary War, and who is ever and anon seen by the country folk hurrying along in the gloom of night, as if on the wings of the wind.”

(from "The Legend of Sleepy Hallow.")

And this passage is what gives us the nugget of the true story behind Irving’s fictional work. While the ghoulish imagery can be pulled from a number of cultural mythologies—from the Scandinavian Wild Hunt to the Irish Dullahan—it is the Hessian reference that points us to American history and who is the real Headless Horseman.

About 30,000 Hessian, aka German, soldiers served as supporting troops to the British army during the American Revolutionary War (taking place from 1775 until 1783). These Germans quickly developed a reputation for being excellent marksmen and riders, engaging in skirmishes in areas today we’d call “no man’s land.” Soon stories about more sinister activities, like cannibalism, followed them too. In a way, Irving’s Headless Horseman perpetuates this propaganda of the Hessian soldiers as otherworldly.


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