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What is the Headless Horseman?

Dan Cavallari
Dan Cavallari

Perhaps one of Washington Irving’s most well known characters, the Headless Horseman, terrorized the eighteenth century town of Sleepy Hollow in upstate New York. Based on a common folktale, the Headless Horseman fits the mold of many chase stories centered on aggressive apparitions. Supposedly a Hessian soldier around the turn of the nineteenth century, the Headless Horseman originally appeared in Irving’s short story, "The Legend of Sleepy Hollow."

While there have been many variations of the story of this specter throughout the years, including a 1999 movie called Sleepy Hollow that adapted Irving’s original tale for the movie screen, the basic concept contains the basic elements of the original Irving tale. Originally hired to aid in ending the Revolutionary War in America, the Horseman was killed when a cannonball severed his head. He was subsequently buried in Sleepy Hollow and returned as a ghost, terrorizing the small town and surrounding countryside for centuries.

Woman holding a book
Woman holding a book

The protagonist in Irving’s tale is Ichabod Crane, a Sleepy Hollow schoolteacher originally from Connecticut who encounters the Horseman. The Hessian ghost rides with his severed head resting on his saddle as he chases Crane. In Irving’s tale, published in 1820, the Headless Horseman pursues Crane until he crosses the town bridge. The Horseman does not follow, but instead throws his severed head at Crane.

Later, Crane’s hat is found with a shattered pumpkin next to it, supposedly used as a prop to imitate the Horseman’s severed head. At this point in the story, there is much debate as to what happened to Crane. Some villagers allege Crane was killed or carried off by the Horseman, while others believe Crane simply fled in fear. By the end of the story, an implication arises that the Horseman was actually Brom Bones, the man Crane had been competing with for the hand of Katrina Van Tassel.

The story itself fits the mold of many folk tales about ghostly chases, but the Headless Horseman has worked its way into popular culture as well as literary legend in a way few other characters have done. Irving’s creation, as well as its ambiguity in the story -– was it really a ghost, or was it simply Brom Bones’s ruse to drive off Crane? -– makes it a particularly chilling character since it blurs the line between human aggression and that of ghosts and spirits.

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Discussion Comments


I can remember watching Sleepy Hollow when I was young and there absolutely no other movie that terrified me than that.

Just the fact that there was someone out there without his/her head scared me to point of bedwetting!!!!

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