The Real Legend Of Sleepy Hollow

Where the Headless Horseman Lost His Head

Exploring Washington Irving’s Hudson Valley Haunts

In the summer of 1798, an outbreak of yellow fever in Manhattan sent a 15-year-old Washington Irving upriver to the home of his childhood friend James K. Paulding in Tarrytown.

Irving remained healthy but became smitten with something else: the rustic and spirited surroundings of what would eventually become Westchester County. He later settled in the area, and throughout his career as an internationally acclaimed author, he wove the local landscape and its inhabitants into his writings.

Since then, Irving’s character Diedrich Knickerbocker has lent his name to beer and basketball, and the author’s Rip Van Winkle is invoked to mock people who seemingly have let time pass them by.

The Headless Horseman from “The Legend of Sleepy Hollow” has inspired movies, music and even a Lego figure; he appears in the lyrics of Kanye West and is currently starring in a network television series.

But what of Irving himself? Who was the man whose lore continues to pervade our culture?

Washington Irving (April 3rd, 1783 – November 28th, 1859)

“He wraps his identity into so many different layers,” said Michael Lord, associate director of education at Historic Hudson Valley, the educational organization based in Tarrytown that oversees Sunnyside, Irving’s former home, and other historic sites.

Irving was a historian and a statesman in addition to being the author of about 20 books, depending on how you count them. He wrote fiction, biographies, essays, travelogues, plays and poetry, sometimes using pseudonyms that included Jonathan Oldstyle, Gent.; Geoffrey Crayon, Gent.; Fray Antonio Agapida and Diedrich Knickerbocker.

The youngest of eight surviving children, Irving was born in Manhattan at the close of the Revolutionary War. He began writing as a teenager and was in his 20s when he gained attention at home and overseas for his satirical “A History of New York, From the Beginning of the World to the End of the Dutch Dynasty, by Diedrich Knickerbocker.” Knickerbocker reappeared in Irving’s next collection, “The Sketch Book of Geoffrey Crayon, Gent.,” as the attributed source for the author’s most enduring stories, “Rip Van Winkle” and “Sleepy Hollow.”

Irving compiled “Sketch Book” during a 17-year stay in Europe, where his reputation and interests expanded. While living in Spain, he served as an attaché at the United States Embassy in Madrid, and wrote books about Christopher Columbus, the conquest of Granada and the Alhambra palace. In 1835, upon returning to New York, he bought a farmhouse on the banks of the Hudson River, located on the border of Tarrytown and Irvington, and transformed it into Sunnyside. Aside from a four-year stint as ambassador to Spain in the 1840s, he lived in the home for the rest of his days.

Jonathan Kruk performing “The Legend of
Sleepy Hollow” in the Old Dutch Church
in the village of Sleepy Hollow.Credit Tom Nycz

Irving never married, but the estate was always bustling. He shared the residence with his extended family, and the construction of the railroad shortly after his arrival meant convenient transportation for his numerous guests. He entertained politicians and artists; as the first American author to earn a living from his writing, he became a role model for younger writers like Charles Dickens, James Fenimore Cooper and Edgar Allan Poe. “He was the first celebrity to move here,” Mr. Lord said.

Irving went on to write biographies of the poets Oliver Goldsmith and Margaret Miller Davidson and of the prophet Mohammed. His final work was a five-volume biography of George Washington. But before tackling that, he resurrected Diedrich Knickerbocker and Geoffrey Crayon to narrate some of the stories in “Wolfert’s Roost and Miscellanies.”

In that collection, published in 1855, four years before he died, Irving returned to the haunts of his youthful summer, where the Pocantico River was a “perfectly wizard stream” and Sunnyside “a little old-fashioned stone mansion, all made up of gable-ends, and as full of angles and corners as an old cocked hat.”

People interested in learning more about Sunnyside’s clever and multifaceted occupant can take a tour through those angles and corners. As conceived by Irving, the design of Sunnyside was indeed eclectic. “He took cues from his travels in Europe,” Mr. Lord said, “from the stepped gables, to the English cluster chimneys, to the Italianate pagoda. Sunnyside was iconic even in Irving’s day.”

Inside, the house remains much as it was when Irving lived there. Many of his possessions are on view, including his oak partner’s desk, his favorite Voltaire chair and his walking stick.

Not far from Sunnyside is a memorial to Irving, erected in 1927, that features sculptures by Daniel Chester French, who created the seated president in the Lincoln Memorial. A bust of Irving is flanked by two of his characters, King Boabdil of Granada and Rip Van Winkle, who slumbered in the Catskill Mountains through the Revolutionary War. Another Rip Van Winkle sculpture can be found on a patch of grass a few blocks to the south. There, Rip is bearded and bewildered, newly awakened from his two-decade nap.

The most indelible aspect of Irving’s legacy lies in the village of Sleepy Hollow, which the author endowed with a “drowsy, dreamy influence” and described as a “lap of land, among high hills, which is one of the quietest places in the whole world.” Nevertheless, it was here that the Headless Horseman terrorized the gangly Ichabod Crane one crisp autumn night. It is easy to retrace that fateful ride, north on Route 9 from the Van Tassels’ house (now the Landmark Condominium in Tarrytown), past Patriots Park, over the Pocantico to the 17th-century Old Dutch Church. In “Sleepy Hollow,” Ichabod was the choirmaster at the gambrel-roofed church, where, Irving wrote, the “peculiar quavers” of his resounding voice can still be heard.

Visitors can wander among the gravestones in the burial ground that abuts the church, where Irving cavorted as a teenager; in “Wolfert’s Roost,” he apologized for “the thoughtless frolic with which, in company with other whipsters, I have sported within its sacred bounds.”

Irving’s own grave is on a hillside in the adjacent Sleepy Hollow Cemetery. On Thursday at 7 p.m., in the chapel on the grounds, David Neilsen will present “Beyond the Legend: Irving’s Ghost Stories,” a reading of some of the author’s lesser-known tales.

This being Halloween season, “The Legend of Sleepy Hollow” is center stage. Historic Hudson Valley offers three ways to experience the story.

“Irving’s Legend,’ ” at the Old Dutch Church, is a one-man re-enactment by Jonathan Kruk, an award-winning Hudson Valley storyteller who dresses in period attire and is accompanied by organ music.

“Horseman’s Hollow” turns nearby Philipsburg Manor into an interactive haunted environment populated by ghoulish creatures including, of course, the Headless Horseman.

At Sunnyside, “The Legend Behind the ‘Legend’ ” is an exhibition of related artworks, objects and memorabilia, along with storytelling, shadow puppets, craft activities, 19th-century games and a spooky walk around the property.

Last month, Penguin Classics published “The Legend of Sleepy Hollow and Other Stories,” a new edition of Irving’s “Sketch Book.” Elizabeth L. Bradley, an Irving scholar and literary consultant to Historic Hudson Valley, wrote the introduction and notes. Ms. Bradley said the book’s release was timely. “I love that everyone has some ownership over Irving’s stories,” she said, “but people forget the provenance. It seemed like a good moment to revisit it.”

In the book, Ms. Bradley describes Irving as “the architect of America’s founding mythology.” Referring to “Rip Van Winkle” and “The Legend of Sleepy Hollow,” she said: “Even now, there is something about these stories that transcends ethnic background, educational level and economic situation. Irving peopled the Hudson River Valley with characters who have become so thoroughly absorbed into the fabric of our lives that we can’t extricate them from our own perspective. They have that kind of pull. They’re just part of you.” — Susan Hodara | New York Times