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Sleepy Hollow, New York
Sleepy Hollow, New York | © Doug Kerr / Flickr
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The True Story Behind Washington Irving’s “The Legend of Sleepy Hollow”

Picture of JW McCormack
Updated: 28 March 2018
Aside from certain penny dreadfuls and the sensational frontier-based Leatherstocking Tales (including The Last of the Mohicans) by James Fenimore Cooper, American literature truly begins with the peerless Washington Irving, whose novellas Rip Van Winkle (1819) and The Legend of Sleepy Hollow (1820) put U.S. writing on the map, with the American character—hardy, commercial, and somewhat naïve—already intact. While Rip Van Winkle had the title character encountering ghostly Belgium settlers in the Catskills, The Legend of Sleepy Hollow had its genesis in English and German-Irish storytelling traditions. Folktales featuring the Headless Horseman were already the order of the day in Europe, but Irving transposed these legends to the young country, where feckless schoolteacher Ichabod Crane is bamboozled by locals masquerading as the horse-riding phantasm.
Ichabod pursued by the Headless Horseman | © F.O.C. Darley / WikiCommons

Irving knew his subject intimately; during the Revolutionary War, upstate New York was infested with refugees and marauding mercenaries. Once the Bronx River was abandoned by the Continental Army in 1776 following the Battle of White Plains, the Americans fled north of Peekskill, with Westchester County left a scorched wilderness, fraught with vigilantes and unaligned raiders. Irving found his inspiration in the discovery of a headless corpse—believed to be that of a Hessian soldier felled by a cannonball—in the quiet community of Sleepy Hollow. As for Ichabod Crane, the uptight schoolteacher’s real-life counterpart was an army captain serving in Sackets Harbor and recorded by New York Governor Daniel D. Tompkins. Additional inspiration may have come from one Jesse Merwin, a well-known teacher and staple of Kinderhook, a hamlet located along the Hudson River.

First appearing in Irving’s The Sketch Book of Geoffrey Crayon, Gent. and attributed to the fictional Crayon, a supposed historian of the American frontier, The Legend of Sleepy Hollow quickly became a signature American fable and was regularly read aloud during Halloween festivities. Irving writes, “From the listless repose of the place, and the peculiar character of its inhabitants, who are descendants from the original Dutch settlers, this sequestered glen has long been known by name of Sleepy Hollow … A drowsy, dreamy influence seems to hang over the land, and to pervade the very atmosphere.” Themes of regional culture, homogenization, and the plight of the outsider pervade the story, in which Ichabod Crane romances the 18-year-old Katrina Van Tassel only to be ousted by Abraham “Brom Bones” Van Brunt, who terrifies Crane by disguising himself as the legendary Horseman. After hurling his severed head in Crane’s direction, the schoolteacher leaves town, leaving only a shattered pumpkin in his wake and allowing Brom to claim the hand of young Katrina.

A portrait of Washington Irving | © Mathew Brady / John Plumbe / WikiCommons

Acclaimed by scholars in America and abroad, the tale quickly became a staple, first appearing in film as the 1922 silent picture The Headless Horseman and later providing Walt Disney with half of his 1949 feature The Adventures of Ichabod Crane and Mr. Toad (the latter being adapted from Kenneth Grahame’s 1980 novel The Wind in the Willow). Future adaptations would include Tim Burton’s 1999 feature Sleepy Hollow, with the Headless Horseman being portrayed by Christopher Walken. A television series of the same name would follow in 2013, with Ichabod Crane as a professor and traitor to the Redcoats who awakens in the 21st century and again encounters the Horseman, the ghost of a soldier Crane had decapitated during the War. But these versions increasingly stray from the regional flavor Irving cultivated in his story. But Irving’s New York roots are far from forgotten in the real Sleepy Hollow (which changed its name from North Tarrytown in 1996). Besides regular Halloween celebrations featuring the Horseman, Sleepy Hollow recalls Irving’s legacy in the name of a high school sports team, the Horseman, and a statue depicting the Headless Horseman on Route 9, a fitting end to the story in which the hapless Crane was finally “spirited away by supernatural means.”