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Inside The Eerie True Stories That Inspired ‘The Legend Of Sleepy Hollow’

Inside The Eerie True Stories That Inspired ‘The Legend Of Sleepy Hollow’

Every year, when the green leaves turn bright orange and pumpkins appear on our doorsteps, Washington Irving’s classic ghost story, The Legend Of Sleepy Hollow, is retold. The beloved American legend follows the tale of Ichabod Crane, a superstitious schoolteacher who finds himself in the haunted town of Sleepy Hollow. There, he suffers an ill-fated encounter with the village’s infamous headless horseman before mysteriously disappearing from the community for good.

While the legend is a staple in American folklore, its inspiration is global. Indeed, Washington Irving’s haunting work is born out of a mixture of foreign lore, local history, and a bit of the uncanny.

The Headless Horsemen That Inspired Sleepy Hollow

The myth of the headless horseman, like much folklore, is shared across cultures. There are iterations of a decapitated apparition on horseback in both Scandinavia and Northern Europe. In Celtic tradition, for instance, there’s the legend of the dullahan, a headless demon who careens about on a black horse. Most famous, perhaps, are the tales of The Wild Huntsman or Der wilde Jäger by German poet Gottfried August Bürger and the German fairytales of writer Johann Karl Musäus, which depict ghostly riders as bad omens.

Well-read and well-bred, Irving certainly would have been exposed to such tales, especially when he went on a European tour and subsequently wrote the collection of short stories The Sketch Book of Geoffrey Crayon, Gent., which included The Legend of Sleepy Hollow.

The American author, however, may have found his inspiration closer to home.

How The Legend Of Sleepy Hollow Borrowed From The Tale Of The Hessian Soldier

A popular myth following the American Revolution was the story of the headless Hessian soldier. Hessians were German troops called upon to aid in Britain’s fight against the American colonists, and one particular Hessian was reportedly decapitated by a cannonball during the Battle of White Plains in 1776.

As the story goes, the corpse of the beheaded Hessian was buried soon after his death at the Old Dutch Church in Sleepy Hollow, near the small village of Tarrytown, New York. It was believed that the Hessian would arise at night in search of his head, and anyone who was ill-fated enough to come across his apparition was condemned to death.

While skeptics of the supernatural could argue against the existence of this headless horseman, historical records show that there actually was a real decapitated Hessian soldier. The haunting tale of the headless Hessian soldier was well-known in the northeast. Coincidentally, about 10 miles from White Plains, New York, where the gruesome death is said to have happened, a teenage boy named Washington Irving was living with a friend in the small village of Tarrytown.

The Real People And Places Behind The Sleepy Hollow Legend

The true story of Sleepy Hollow can be traced to Washington Irving’s early years. At age 15, Irving left his native home of New York City and made his way north to Tarrytown, where his friend James Kirke Paulding lived.

Around that time in 1798, New York City was gripped by yellow fever, and Irving’s family was among those wealthy enough to leave the city and find refuge elsewhere. They escaped to the fresh countryside of the Hudson Valley, where it’s clear from Irving’s writing that he adored the idyllic, pastoral setting and the eerie feelings inspired by its quaint colonial Dutch architecture.

Irving was particularly mesmerized by the Catskill Mountains, which greatly influenced his creation of The Legend of Sleepy Hollow. Besides having his fictional Sleepy Hollow village modeled off the real town of North Tarrytown in which he lived, the writer also named and loosely based his characters on real people.

The protagonist in Irving’s Sleepy Hollow, Ichabod Crane, is said to have been inspired by Jesse Merwin, a mutual friend the author shared with Martin van Buren, who later became America’s eighth president. Others claimed that the bookish schoolteacher was inspired by Samuel Youngs, a lieutenant from Tarrytown who was friends with the Van Tassel family, who also inspired Irving and appear by name in the folktale.

Katrina Van Tassel, Ichabod Crane’s unrequited love interest, was also presumably based on someone Irving knew personally. The Van Tassels in Irving’s story have money, but the character is based on several real people and a name taken from a gravestone.

There’s also a plague that riddles the little town in Irving’s book, which vaguely resembles the epidemic Irving’s family was forced to flee. All in all, fiction, history, and the mystical meld together in Washington Irving’s famous ghostly tale.

Writing America’s Most Popular Ghost Story

In 1817, Washington Irving’s family business went bankrupt following the British-American War of 1812. So he left New York for Birmingham, England, where his sister Sarah and her husband Henry van Wart were already residing.

It was here that Irving, plagued by writer’s block since the unexpected success of his first book, A History of New-York from the Beginning of the World to the End of the Dutch Dynasty, years before, was struck with renewed inspiration to write. A conversation with his brother-in-law had awakened in him old memories of his time in the Hudson Valley and with it Irving’s fascination with the community’s Dutch past and local lore.

Washington Irving spent all night writing his manuscript. His sister and brother-in-law were the first to hear the opening chapters of his collection of short stories that would later become known as The Sketch Book.

The collection of essays was issued serially throughout 1819 and 1820 under Irving’s preferred pseudonym, Geoffrey Crayon. Its later publication included the short story The Legend Of Sleepy Hollow.

The Sketch Book received rave reviews following its first publication, and critics agreed that the third story, The Legend Of Sleepy Hollow, was the collection’s crown jewel.

Modern Adaptations Of The Enduring Legend

Since it first caught the public’s attention in 1820, The Legend Of Sleepy Hollow continues to be one of the most enduring ghost stories in America. Its tale has been adapted repeatedly and brought to life in numerous ways, inspiring the naming of several towns and villages across the U.S.

Its first-known on-screen adaptation was the 1922 silent film The Headless Horseman, and it has since been retold to viewers again and again. One of the most popular iterations of the story was the 1999 film Sleepy Hollow, directed by Tim Burton and starring Johnny Depp as Ichabod Crane.

Another modern adaptation was the 2013 FOX series Sleepy Hollow, which put an interesting twist on the classic tale by making the ghostly headless horseman one of the Four Horsemen of the Apocalypse and transporting the 19th-century characters into a modern time setting.

No matter how many times it’s retold, The Legend Of Sleepy Hollow, with its unique formula of folklore, history, and mystique, remains a Halloween classic and reaffirms our appetite for the supernatural each and every year.