Halloween History: The Legend of Sleepy Hollow

The Headless Horseman

A.R.,engraver. The Headless Horseman-Sleepy Hollow, 1876. Wood Engraving. New York Public Library, Children’s Book Illustrations.

The origins of “The Legend of Sleepy Hollow” lie shrouded in mystery. Some say that the character of the Headless Horseman was inspired by the German folktale “The Wild Huntsman.” Washington Irving may have heard this tale while traveling abroad. Others insist that the Headless Horseman was based on an actual Hessian soldier who was decapitated by a cannonball during the Battle of White Plains, around Halloween 1776. (Hessian soldiers were troops from Germany hired by the British to fight in the Revolutionary War.)

In “The Legend of Sleepy Hollow” Washington Irving describes the Headless Horseman as “the ghost of a Hessian trooper, whose head had been carried off by a cannon-ball in some nameless battle during the Revolutionary War.”[i] Historical documentation of a headless Hessian soldier does exist. Major General William Heath published a memoir of his Revolutionary War experiences in 1798. On November 1, 1776 Heath wrote in his journal that “A shot from the American cannon at this place [White Plains] took off the head of a Hessian artillery man.”[ii]White Plains is located less than ten miles from Tarrytown. Perhaps this is how the legend was born.

Ichabod Crane and the Headless Horseman

John Rogers, Ichabod Crane and the “Headless Horseman,” 1887. Bronze. New-York Historical Society, 1936. 627

Washington Irving first visited Tarrytown in 1798. A yellow fever epidemic was raging in New York City. Washington Irving’s family fled the city to escape infection. Irving was enthralled by Tarrytown’s Dutch character. The town reminded him of a bygone era. He recounted its quaint customs in “The Legend of Sleepy Hollow,” first published in 1819.

Visiting Tarrytown was a formative experience for Irving. The idyllic countryside captured his imagination. Its hidden valleys and meandering streams had an air of mystery. Irving recalled hearing many legends and ghost stories. “Villagers spoke in hushed whispers of the strange cries heard in the woods where the captured British spy John Andre had been hanged.”[iii] His sojourn in the Hudson River Valley inspired many of his spellbinding tales.

Join us for a spooky Story Time on Sunday October 27th. We’ll be reading Sleepy Hollow and the Road You’d Better Not Follow by Donna Davies.

Sleepy Hollow and the Road You'd Better Not Follow Book Cover

Meet the Headless Horseman and hear master storyteller Jonathan Kruk’s rendition of “The Legend of Sleepy Hollow” at Spirits of Hallowe’ens Past on Thursday October 31st!



[i] Neider, Charles ed, The Complete Tales of Washington Irving (New York: Da Capo Press, 1998), p. 32.

[ii] Heath, William, Memoirs of Major General William Heath (New York: William Abbatt, 1901), p. 73.

[iii] Jones, Brian Jay, Washington Irving: The Definitive Biography of America’s First Bestselling Author (New York: Arcade Publishing, 2011), p. 11.

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