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200 Years of the Headless Horseman

The Legend of Sleepy Hollow is a famous short story by American author Washington Irving. Every American schoolchild is probably familiar with the tale of the Headless Horseman that terrorizes the outskirts of Sleepy Hollow, including the poor schoolteacher, Ichabod Crane.

Sleepy Hollow was first published in 1820 in a collection of works published under one of Irving’s many nom de plumes, The Sketch Book of Geoffrey Crayon, Gent. That collection also contained another fantastic tale for which he is much remembered – Rip Van Winkle. 

A beautiful edition illustrated by Arthur Rackham. Listed for sale by John Windle Antiquarian Bookseller.

Neither of those famous tales might exist if not for Irving’s visit to the Catskill Mountains of upstate New York. The journey was prompted by an outbreak of yellow fever in Manhattan, driving the young Irving upriver to visit a friend in Tarrytown and a nearby small town called Sleepy Hollow. The quaint village with its Dutch customs and ghost stories seemed to enchant the young author, and he revisited them many times in person as well as in his tales years later.

While The Legend of Sleepy Hollow is considered one of the earliest popular American fictions and has become a classic read for October classrooms, the concept of the Headless Horseman is an ancient legend found repeated across Northern European countries. Irving traveled through Europe and picked up a few fantastical threads that he wove into his stories, but it was also inspired by more recent battlefield tales. In 1776, General William Heath reported the gory death of a Hessian cavalryman whose head was carried clean away by a cannonball!

The Sketch-Book Of Geoffrey Crayon, Gent listed by Anniroc Books

The main character of the tale is Ichabod Crane, a gangly, poor schoolteacher who becomes smitten with the lovely Katrina Van Tassel (and her grand inheritance). Crane is tormented by his own shy nature and by a rival for Katrina’s hand – the big local hero, Brom Bones. After a few ill-fated attempts to court Katrina and pranking by Brom and his crew, Crane is ultimately pursued along the road by the Headless Horseman himself! Ichabod is never seen again and we are left to wonder if it was just a prank that caused him to flee in terror, was he murdered, or as the locals preferred to speculate, did Ichabod Crane meet a supernatural demise?

Whatever happened to poor Ichabod may never be certain. We can guess, though, that the Headless Horseman and the town of Sleepy Hollow will continue to be a classic tale of horror told for many more years to come.

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