The Hudson Valley’s Legend of Sleepy Hollow Enchants for 200-Plus Years

The haunting folktale by Washington Irving follows the twists and turns of Ichabod Crane’s encounter with the Headless Horseman.

The haunting folktale by Washington Irving follows the twists and turns of Ichabod Crane’s encounter with the Headless Horseman.

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 term knickerbocker — a denizen of New York City — also springs from Irving’s pen. (New York Knicks, anyone?)

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Ichabod Crane
Ichabod crane flees from a ghostly figure in Frederic Simpson Coburn’s What Fearful Shapes and Shadows Beset His Path (1899)

2019 was the bicentennial of the publication of The Sketch Book of Geoffrey Crayon, Gent., which was serialized between 1819–1820. “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 story was celebrated throughout 2019–2020, and with that came 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 were ‘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.”

An image of Irving’s estate Sunnyside

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.”

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Which 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.”

“Sleepy Hollow,” with its innovative mixture of the American colloquial inflected with a good dose of spooky German folklore, pushed [Irving] into the rank of literary celebrity, one of the first hugely acclaimed writers to come out of the United States.

And 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.

Prior to the COVID-19 outbreak, the beautiful Sunnyside offered tours from May through November (check the website for current tour offerings). Irving, according to Karen 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's Legend
Irving’s Legend presented by Historic Hudson Valley / Photo by Jennifer Mitchell for Historic Hudson Valley

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 — 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 a decade in existence in 2019, and newcomer The Unsilent Picture returned for its second year.

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“Visitation has doubled in this time frame, now approaching 50,000 just for these events alone,” says Clark. “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.” (For more on events, visit

Irving headstone
Irving’s headstone at Sleepy Hollow Cemetery / Photo by James P. Fisher III

In 2019, Historic Hudson Valley launched a brand-new event. “The Sleepy Hollow Experience” was “an outdoor, immersive theatrical experience” that’s “a retelling of ‘The Legend of Sleepy Hollow.’ There was music, and visitors could 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 preferred some historical context amid the spookiness.

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 only be deepened with each year that follows the bicentennial celebration.

Related: The Hudson Valley Was Benedict Arnold’s Downfall

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