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The Truth Behind the Legend of Sleepy Hollow

Take a midnight ride through the historic village of Sleepy Hollow, where Washington Irving's eerie legend lives on.


It’s a tale that sticks with you. A lonely schoolmaster heads out into the night after failing to secure the hand of the woman he hoped to marry. Frightened by his surroundings, the doomed traveler ventures into a dark and dismal grove, where he encounters a cloaked headless horseman—never to be heard from again.

Washington Irving’s, “The Legend of Sleepy Hollow” is the perfect ghost story for this time of year. And while it features a decapitated spirit who haunts the countryside, the legend that is Sleepy Hollow is rooted in truth.

legend of sleepy hollow

In the late 1700s, Tarrytown and its surrounding Hudson Valley hills were nearing the end of the Revolutionary War. The British, still at odds with American raiders, called upon German mercenaries, or Hessian Jagers, to assist in the fight. The Hessians were notoriously ruthless soldiers who killed without mercy. Irving’s Headless Horseman, a Hessian soldier himself, is rumored to be inspired by an actual decapitated Hessian corpse, exhumed from an unmarked grave in the local cemetery of the Old Dutch Church.

legend of sleepy hollow

As for the story’s setting, Irving writes that the sequestered glen of Sleepy Hollow is “one of the quietest places in the whole world” located mere miles from historical Tarrytown, New York. While Irving invented Sleepy Hollow for his eerie tale, the real-life residents of North Tarrytown have long believed it to be based on their own village—so much so that in 1996, North Tarrytown officially changed its name to Sleepy Hollow.

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And it’s everything you want it to be, especially in the weeks leading up to Halloween. By day, Sleepy Hollow is a picture-perfect village, abuzz with autumnal festivities. Revelers arrive early for pumpkin fairs, spiced craft beers (the Ichabod Crane at The Huddle is a must), and walking tours of the Horseman’s old stomping grounds. Washington Irving and the inspirations behind his characters are actually buried in the cemetery at the Old Dutch Church.

legend of sleepy hollow

Yet it’s when the sun goes down that the dark legend of Sleepy Hollow truly comes to life. Ghosts and goblins appear in the night, while a costumed Headless Horseman roams the streets. The sunbeams that once romanced the gravestones of the Old Dutch Church cemetery transform into sinister shadows that play tricks on the eye. The moon casts a spooky glow as murmurs of a live “Sleepy Hollow” reading escape the stone church. Across the street, a haunted house, which incorporates the infamous bridge from the story, is in full swing.

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legend of sleepy hollow

For fans of historical towns with a ghostly cheer, a visit to Sleepy Hollow is a must. Maybe, just maybe, you’ll hear the distant sounds of Ichabod upon his plow horse, chanting his psalm—or perhaps you’ll come face-to-face with the Headless Horseman himself.

legend of sleepy hollow

Feature photo: cgc76 / Flickr; all other photos courtesy of DeAnna Janes