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The Legend of Sleepy Hollow: Hidden History in an American Ghost Story

“The dominant spirit, however, that haunts this enchanted region, and seems to be commander-in-chief of all the powers of the air, is the apparition of a figure on horseback, without a head.”

Americans love a good ghost story—and what better time to indulge this guilty pleasure than Halloween? This season we’re looking back to what might be the OG of all-American ghost stories, Washington Irving’s The Legend of Sleepy Hollow, which celebrates its 200th anniversary this year. First published in 1820, the short story has inspired countless adaptations, perhaps most famously Tim Burton’s 1999 Sleepy Hollow, starring Johnny Depp as a squeamish and fearful Ichabod Crane. This interpretation couldn’t be further from Irving’s original Ichabod who, just like us, relished spending winter evenings hearthside, listening to “marvelous tales of ghosts and goblins, and haunted fields, and haunted brooks, and haunted bridges, and haunted houses, and particularly of the headless horseman.” Americans’ timeless love of a good ghost story seems itself engrained in Sleepy Hollow, and Irving’s short story has continued to terrify us for the past 200 years. You might be too distracted with fright to realize that there is some hidden Revolutionary War history embedded in this spooky tale.

The Miriam and Ira D. Wallach Division of Art, Prints and Photographs: Picture Collection, The New York Public Library. “The headless horseman–Sleepy Hollow.” The New York Public Library Digital Collections. 1876. http://digitalcollections.nypl.org/items/6c065365-4c4c-4f8b-e040-e00a180645a8

The Legend of Sleepy Hollow takes place in 1790, just after the American Revolution, and if you read closely enough, the war itself is a powerful character and a driving force in the narrative. When Ichabod Crane arrives in Tarrytown and becomes part of the community at Sleepy Hollow, the residents have begun to heal from their Revolutionary past. Irving tells us “the British and American line had run near (the neighborhood) during the war; (and) had been the scene of marauding and infested with refugees, cowboys, and all kinds of border chivalry.” While by no means should one read Irving’s short story for its historical accuracy, this characterization of Sleepy Hollow’s situation in the Hudson River Valley is not far from historical truth. During the Revolution, the Hudson River Valley hosted more than its fair share of skirmishes as passionate patriots clashed with steadfast loyalists and armies from both sides besieged the Valley, but Westchester County (where Tarrytown, now more widely known as Sleepy Hollow, is located) was effectively considered “neutral ground,” wherein neither the American army to the north nor the British army to the south laid considerable claim or control. This distinction created conditions ripe for violence and left the county’s civilian population so vulnerable that, according to Timothy Dwight, chaplain to the Connecticut brigade, “they feared everybody whom they saw; and loved nobody…fear was the only passion by which they were animated.” Dwight’s recollections from his 1777 stay in the county paint a desolate picture of terrified residents, “their houses…scenes of desolation. The walls, floors and windows were injured by both violence and decay; and were not repaired, because they had not the means of repairing them, and because they were exposed to the repetition of the same injuries.” Civilians with means took what little they had and escaped to safer houses of friends and relatives outside this “neutral ground;” others made makeshift camps elsewhere.

This is the very real landscape in which Washington Irving set his grisly tale, where within this context it is believable that a menacing force perpetuated violence on the community, even after death. But what of the headless horseman himself? It’s easy to miss this detail for the more attention-grabbing decapitation in Irving’s short story—the headless horseman at the heart of the tale is said to be a Hessian soldier from the American Revolution:

“It is said by some to be the ghost of a Hessian trooper, whose head had been carried away by a cannon-ball, in some nameless battle during the Revolutionary War, and who is ever and anon seen by the country folk hurrying along in the gloom of night, as if on the wings of the wind…”

Historians have long mused on Irving’s historical inspiration for his headless Hessian, if one exists at all. The British hired upwards of 30,000 German troops to support the war effort against the rebelling colonies, most of them coming from the German state of Hesse-Cassel (thus, Hessians). Hessian soldiers had a reputation for brutality on and off the battlefield, making a Hessian, headless or not, a viable foe—and Hessians were certainly partly to blame for the deteriorating conditions in the region’s “neutral ground.” Some Sleepy Hollow enthusiasts suggest that Irving was inspired by local lore surrounding the actions not of a violent Hessian, but a sympathetic one who, as legend has it, helped save the life of a civilian after one of the region’s violent raids. When the civilian’s family later found a headless Hessian presumed to be their family’s savior, they buried him—sans head—in the Old Dutch Burial Ground.

If Irving was inspired by any real revolutionary history at all, the most likely “nameless battle” in which Irving’s horseman may have met his demise might in fact be the Battle of White Plains, in which British General William Howe defeated Washington’s troops on October 28, 1776 (conveniently close to Halloween), just 8 miles east of Tarrytown/Sleepy Hollow. There, Hessian troops helped to break the American line and contributed to the British victory, but not without withstanding casualties. American Major General William Heath wrote of the battle in his journal (which he published in 1798), noting that “a shot from the American cannon at this place took off the head of a Hessian artillery man.” Whether Irving read and delighted in this grisly anecdote is unknown, but nonetheless there is a small grain of truth in every fiction—an unfortunate Hessian did lose his head a mere 8 miles from Sleepy Hollow.

Regardless of what—if any—real history inspired Washington Irving’s tale, The Legend of Sleepy Hollow provides an engaging launch to explore lesser-known Revolutionary War history (and this is just the beginning—“André’s tree” is for another blog entirely).

This Halloween, treat yourself to a read of America’s original ghost story!

Read The Legend of Sleepy Hollow online: https://www.gutenberg.org/files/41/41-h/41-h.htm

Katherine Egner Gruber
Special Exhibition Curator, Jamestown-Yorktown Foundation


Selected Sources

The American Revolution in the Hudson River Valley, National Park Service: https://www.hudsonrivervalley.com/documents/109744hudsonrevolution2-pdf

The Revolutionary War “Neutral Ground” of Westchester County, National Park Service: https://www.nps.gov/sapa/learn/historyculture/upload/neutralgroundwebsitearticle.pdf

The Battle of White Plains, Washington Library Digital Encyclopedia: https://www.mountvernon.org/library/digitalhistory/digital-encyclopedia/article/battle-of-white-plains

Halloween History: The Legend of Sleepy Hollow, New-York Historical Society: http://historydetectives.nyhistory.org/2013/10/halloween-history-the-legend-of-sleepy-hollow


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