Every Halloween you start hearing whispers about Ichabod Crane and the Headless Horsemen. The Legend of Sleepy Hollow is considered one of America’s first horror ghost stories and it scared the bejeebies out early settlers. Why be worried about witches when the Headless Horsemen was coming after you? 

Legend of Sleepy Hollow
The Legend of Sleepy Hollow By Washington Irving

Is The Legend of Sleepy Hollow Based on a true story?

The origin of this tale is covered in mystery and intrigue. While Washington Irving was not the creator of the headless dooms bringer, it is believed he found inspiration from a German folktale called “The wild huntsmen”. Others believed it to be based off a Hessian Trouper (German hired to fight for the British during the revolutionary war) whose head was removed by a cannon ball.

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The New York Historical Society cites that there was a soldier who had his head removed via canon fire in 1776 — documented in a memoir of an American general fighting the Revolutionary War in TarryTown. In the folklore itself they claim the headless horsemen is a soldier looking for his head who roams along a bridge searching for his lost head and any who dare get in his way will suffer the same fate in a flash of fire and brimstone. 

Legend of sleepy hollow Headless Horseman depiction
A take on what could be the Headless Horseman

It’s said that this tale was highly believed and many people in the small villages around, everyone knew about the Headless Horseman. The tale of the Headless Horseman found itself being re-told in many ways but each one managed to incite fear and wondering in the villagers. How do we think these villagers would have handled the true story of Countess Bathory or any of our horror podcasts we secretly love to listen too?

In 1996 the real life town of TarryTown officially changed its name to Sleepy Hollow. Fully embracing the spooky life and becoming a part of the horror fiction tale that is the Headless Horseman. Here you can find the grave of Washington Irving and many country roads and bridges that are eerily similar to those written about in the tale Sleepy Hollow. 

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Grave Yard
Sleepy Hollow’s Grave Yard

The tale of the Headless Horseman is riddled with history, the truth and the supernatural. Take a peek below if you’re curious — or grab a copy of the story and read Washington Irving’s tale from the source. 

Ichabod Crane and Sleepy Hollow

Ichabod Crane accepted the position of school master in the village of Sleepy Hollow. Sleepy Hollow was a Dutch settlement nestled in rolling hills of New York. At that time, the Dutch were perceived to have a strong belief of ghost stories and loved to tell these re-told tales around town. It was even said that Sleepy Hollow was encased in mystery and intrigue so strong that ghosts and the supernatural seemed to be more abundant here.

Is Ichabod Crane a real person?

Ichabod was such a guy to fall prey to all the ghost stories whispered into his ears. While teaching he would rotate from family to family who would host the school teacher for a week or so. And during a stay with a family is when he learned about the most harrowing tale — the Headless Horseman. It was said that the ghost of a Hessian  soldier who lost his head during the American Revolution was constantly in search of his head and frequented the old church where it was said he was lain to rest. 

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As fate would have it, Ichabod has a student who he falls head over heels for. Katrina Van Tassel the only child of Baltus Van Tassel, a farmer who is amassing great wealth. Ichabod imagines himself in love but whether his affection is for Katrina or her fortune , we are a bit unsure there. this sparks a rivalry from the athletic and complete opposite of Ichabod— Brom Van Brunt.

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One day Ichabod is invited to a huge soiree at Katrina’s. But when the evening starts to wrap up he is somehow spurned by Katrina and leaves in a flurry of emotions.  Alone at midnight on the eerie country roads he lets his imagination start to run wild.

He passes a historical landmark called the hanging tree— where many died during the war. There he sees him — the Headless Horseman. The Headless Horseman starts to follow Ichabod down the road. The teacher tries to loose him, but he sticks to him like glue. As he is galloping away from the Headless Horseman, he stumbles upon the church yard and beyond is a bridge which local legends claims the Headless Horseman does not cross. Ichabod manages to cross to safety, but he makes the classic mistake of looking back once across. As a final warning the Headless Horse man throws his head at Ichabod.

The following morning all that is found of Ichabod is his hat and a smashed pumpkin. Whether the teacher ran off or was captured by the Headless Horseman no one ever figured it out. 

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