The True History Behind “The Legend of Sleepy Hollow”

Largely forgotten today, Washington Irving has an odd historical legacy.

The Headless Horseman Pursuing Ichabod Crane (1858) by John Quidor | Google Art Project

Largely forgotten today, Washington Irving has an odd historical legacy that dips deep into the families and lands of Westchester County.

The tale of Rip Van Winkle, the man who famously fell asleep for years and years and awoke to a changed, unfamiliar world, is about as familiar as it gets when it comes to American folklore. Likewise is the famously tall and gaunt Ichabod Crane (“one might have mistaken him for … some scarecrow eloped from a cornfield”), scared out of his wits in “The Legend of Sleepy Hollow” by the terrifying, blood-curdling sight of the Headless Horseman.

As rooted in folklore as “Rip Van Winkle” and “The Legend of Sleepy Hollow” are, they are not, in fact, popular legends and myths that sprang up during the early years of the United States — they are works of fiction penned by Washington Irving.

Largely forgotten today, Washington Irving has an odd historical legacy. His literary output has long been a part of the American vernacular, yet the actual source of these writings — the author himself — has basically fallen into obscurity. If this were not influence enough, the word “knickerbocker— a denizen of New York City — also springs from Irving’s pen. (Hence the nickname of the storied NYC NBA franchise. )

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The year 2019 marked the bicentennial of the publication of The Sketch Book of Geoffrey Crayon, Gent., which was serialized between 1819 and 1820. “The Legend of Sleepy Hollow” was published as part of The Sketch Book in March 1820. Because of the serialization, the anniversary of the Sleepy Hollow-based short story was celebrated in 2019–2020, and with that comes an opportunity to restore Washington Irving to his rightful stature.

The physical and psychological landscape of the Hudson Valley are part and parcel of Irving’s most famous fictional creations. “Sleepy Hollow” transpires near “Tarry Town” (as Irving styled it), “a retreat whither I might steal from the world and its distractions and dream quietly away…”

Washington Irving lived and worked here in the Hudson Valley, and the region’s beauty and mystery remain forever linked to his writing output. Sleepy Hollow is a real place, of course, as is Tarrytown. Irving is the namesake of the village of Irvington. Local drivers can avail themselves of the Rip Van Winkle Bridge. It doesn’t take much to ascertain his regional influence.

As a town, “the legacy of Sleepy Hollow and that of Washington Irving are closely shared,” according to Henry Steiner, official historian for the Village of Sleepy Hollow. “Sleepy Hollow has been influenced by Irving, and Irving by Sleepy Hollow. One legacy would not be the same without the other. Irving was a prolific writer, but his two most famous, iconic works are ‘The Legend of Sleepy Hollow’ and ‘Rip Van Winkle.’ Sleepy Hollow is the real place that inspired Irving’s best work, and the reception of this short masterpiece was instrumental in establishing Irving’s great fame. He returned the favor by making Sleepy Hollow, the place, world-famous.”

Irving’s expansive estate, Sunnyside, is located in Tarrytown and is an active historical and educational site that hosts a wide range of visitors. Sunnyside, according to Historic Hudson Valley’s Karen Clark, celebrates Washington Irving “and his impact on the region and on literature in general. He had a lasting impact on our culture.” This makes his general unfamiliarity today all the more puzzling. The young United States of the early 19th century, flush with independence, nevertheless struggled with a deep-seated inferiority complex. Europe was the fount of culture and knowledge. “Writing in New York at the beginning of the 19th century,” according to scholar William L. Hedges, “meant writing for an audience bent on viewing itself as sophisticated.”

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Irving did not disappoint. “Sleepy Hollow,” with its innovative mixture of the American colloquial inflected with a good dose of spooky German folklore, pushed him into the rank of literary celebrity, one of the first hugely acclaimed writers to come out of the United States. Other writers of the time — like Edgar Allan Poe — were eager for his approval. The public clamored for his autograph. He broke bread with President Martin Van Buren. Irving’s friendly letter to Charles Dickens thrilled the British writer to no end — such was the international renown of Washington Irving.

sleepy hollow horseman
The Headless Horseman at Philipsburg Manor, part of the Horseman’s Hollow haunted attraction. Photo by Jennifer Mitchel; Historic Hudson Valley

The beautiful Sunnyside offers tours from May through November. Irving, according to Clark, “actually designed his home and designed the landscape, as well, creating ponds, vistas, a garden.” Besides being a place of striking visual attractiveness, Sunnyside also functions as a student-friendly educational resource, with school group tours and events specifically geared toward the younger set.

Irving spent many, many years in Europe (duly noted and criticized in some quarters) and, in the 1840s, served as American minister to Spain. Sunnyside, though, was eventually his permanent home, where he wrangled with publishers, lived amid his large extended family, and over a lifetime produced an astonishingly varied, prodigious output that ran the gamut from fiction, essays, biographies, travelogue, and — perhaps most surprisingly — a work on the Prophet Muhammad.

The Headless Horseman is a true staple of the fantastic. Not surprisingly, interest in “Sleepy Hollow” spikes during the Halloween season, and with that are added visitors to the village and the Historic Hudson Valley properties. Popular events “Horseman’s Hollow” and “Irving’s Legend” celebrated their 10th year in 2019, thanks to their popularity among locals.

“Visitation has doubled in this time frame, now approaching 50,000 just for these events alone,” says Clark of the 2019 season. “In all, we’ll welcome well more than 250,000 people from all 50 states and several countries to greater Sleepy Hollow country this fall. We are proud to help drive this tremendous economic engine for the area.

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in 2019, Historic Hudson Valley launched a brand-new event. “The Sleepy Hollow Experience” was “an outdoor, immersive theatrical experience [that is] a retelling of ‘The Legend of Sleepy Hollow.’ There’s music, and you can follow the characters from scene to scene around the grounds,” according to Clark. Historic Hudson Valley also had experts on hand during another event, named “Home of the ‘Legend,’” at Sunnyside for those who sought some historical context amid the spookiness.

That context does not negate the role of Washington Irving as a writer. In April 2020, Historic Hudson Valley planned to participate in an academic conference — open to the general public — that was set to convene to discuss Irving’s enduring importance.

More than two hundred years ago, the world read the jolting words that “Ichabod was horror-struck on perceiving that [the horseman] was headless! but his horror was still more increased on observing that the head, which should have rested on his shoulders, was carried before him…” And generation upon generation has collectively shivered. Washington Irving’s considerable legacy endures and should be only deepened since the bicentennial year.

Richard Klin in an author based in the Hudson Valley and the author of the novel Petroleum Transfer Engineer (Underground Voices, 2018).

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