The Legend of Sleepy Hollow: Haunted Through the Ages

Written By: Angela DiLella

Edited By: Grave Reviews Staff

 

The Legend of Sleepy Hollow

Is there a more classic Halloween tale than “The Legend of Sleepy Hollow”? The story by Washington Irving, which tells the tale of a young schoolmaster named Ichabod Crane who comes face to face with a headless horseman, has remained popular since its first publication in 1820. It has even been adapted as both live and animated films and was loosely adapted into a television show simply called Sleepy Hollow in 2017.

The story is set in the village of Sleepy Hollow, a small village in Tarrytown, New York, where Irving spent the majority of his teenage years, and would spend many years of his later life. Until 1996, the area was officially recognized as North Tarrytown, though locals had called the area Sleepy Hollow for centuries. In 1996, the name was officially changed from North Tarrytown to Sleepy Hollow.

Irving’s Inspiration and Adaptation

In “The Legend of Sleepy Hollow,” the headless horseman was identified as a Hessian, a German mercenary, who had his head knocked off by a cannonball during the Revolutionary War. Although Irving claims the horseman’s demise occurred during “some nameless battle,” Major-General William Heath claimed it happened during the Battle of White Plains specifically. The nameless Hessian was eventually buried in the Old Dutch Church’s burial grounds without his head. Historically, this checks out, and the Major-General naming the battle where an unfortunate mercenary was killed gives the legend even more credence.

But could the village of Sleepy Hollow really be haunted?

There are several different tales of the headless soldiers haunting the area in and around Sleepy Hollow. Although it seems clear that Irving borrowed many concepts from the local folklore for his tale, it’s hard to say which of the many stories he would have known and drawn inspiration from. The second most popular headless ghost in the area (most often seen north of Sleepy Hollow near Teller’s Point) is recognizable because of his full Hessian regalia, but lacks the horse. Another headless ghost has been spotted near the Rogers-Haight Homestead. A popular tale at the homestead says a soldier lost his head—literally—over an argument about a pig: a notably less dramatic backstory for the horseman.

Many claim to see Irving’s horseman near the Old Dutch Church and Burial Ground where he is said to be buried, making his nightly rounds. You can also find the graves of people upon which Irving based major players in his now-famous story, though they are apparently much quieter than the horseman’s apparition. Even Ichabod Crane, who was said to not be too pleased with Irving’s use of his name, stays quiet in his patch of the cemetery.

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GLENN DALE HOSPITAL, A FORMER TUBERCULOSIS HOSPITAL IS SAID TO BE ONE OF THE CREEPIEST PLACES TO VISIT. TODAY IS IT IN DISREPAIR AND STANDS ABANDONED.

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Although no other ghosts are named specifically in Irving’s famous short story, he does mention “strange sights, and… music and voices in the air” as well as “haunted spots.” Everything from wailing women in white to the famous haunted ship, the Flying Dutchmen, are said to be seen (or heard) in the area. Other ghostly ships and their unfortunate crews are also said to dock in the Tappan Zee, a lake like part of the Hudson River that is near Tarrytown and Sleepy Hollow. Even further back in history, Native Americans blamed the spirits of people that drowned in the Hudson River for its unpredictable waters. Many individual homeowners say their homes are haunted as well.

Even Irving’s home in the area, Sunnyside, is said to be haunted. It was a rumor that it was haunted long before he ever moved in on 1835. The house was originally built in 1656, so it would have had plenty of time to amass ghosts! Irving said that he sometimes saw the spirit of a young woman wandering Sunnyside’s orchards from time to time, and others claimed to have also seen Sunnyside’s original seventeenth-century owner. Now it is commonly believed that Irving’s five nieces and his love, Matilda Hoffman, haunt the grounds, too.

Honoring the Legend Today

The story is further honored every year in the town made famous by it with cemetery tours that run throughout the summer and fall. There is also a walking tour over Horseman’s Hollow, meant to terrify and titillate, as well as a similarly themed haunted hayride. Finally, just before Halloween, author and storyteller David Neilsen reads some of Irving’s ghost stories at the Washington Irving Chapel in Sleepy Hollow Cemetery. The tickets to these events sell out months in advance.

“The Legend of Sleepy Hollow” is so ingrained in American culture that there are other towns named Sleepy Hollow across the country that also celebrate the tale—or at least borrow the headless horseman for Halloween festivities! If you missed out on reading Irving’s tale in school, now is as good a time as any to do so and see what the nearly 200 years of fuss is all about! And you might find yourself compelled to book a trip to New York soon afterwards.

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