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The Real Story of Sleepy Hollow

Updated on January 10, 2020

Few stories have captivated and horrified the minds of young readers quite like Washington Irving's short story The Legend of Sleepy Hollow. Personally, as a child, I was terrified by the book but at the same time intrigued by the story. In my mind, the very idea of such a being was implausible and unrealistic; yet, at the same time, I hoped that at least part of it was based off of some historical sightings of the headless Hessian. An account that would keep that sliver of hope that something so fanciful could exist.

A couple of years ago my father-in-law passed away and my wife and I went to bury his ashes in the small town of Hortonville, New York where my wife's family was from. As I was searching around the state for interesting places to visit, I happened to come across the town of Sleepy Hollow, New York. As you can imagine, I was quite intrigued that such a place actually existed and couldn't wait to view it in person.

The town itself didn't disappoint, as it was just as I had imagined it to be. A small town with even bigger stories. The gravesites with the names of the actual characters from the story were in an old graveyard dating back to the time of the legend and the town itself presented an aura of a mixture of folklore and history. All in all, it was an exciting trip, even though, I was disappointed that the old bridge that the Headless Horseman couldn't cross in the story was no more.

Seeing it in person brought about a renewed interest in the subject and I wanted to know more; I wanted to see through the eyes of Washington Irving and envision for myself the truth behind the tale. To my delight the internet was ripe with answers.

The Real Sleepy Hollow

As it turns out, Washington Irving, the author of The Legend of Sleepy Hollow actually knew a man named Ichabod Crane who lived in the area around what is now known as Sleepy Hollow. However, as it turned out, the man was the furthest thing from a cowardly school teacher of the same name. The real Ichabod was a career soldier born in Elizabeth, New Jersey. He was a Marine and U.S. Army officer who fought in the War of 1812. During the war, he was stationed at Fork Pike in Sackett's Habor, New York. While there, he met Irving who was an aid to then New York Governor Daniel Tompkins.

Now that we have established where Irving got the name Ichabod Crane and that the real Ichabod was nothing like the one in Irving's story. That still leaves the question of who was Ichabod Crane based off of? After all, his real-life counterpart was the complete opposite of the fictional one. Well some say that Ichabod Crane's demeanor was based off of another person that Irving had been acquainted with during his time in Kinderhook, New York. Jesse Merwin who was originally from Connecticut had settled in the small town of Kinderhook. He was a teacher by trade and according to letters between he and Irving, Merwin was sincerely honored to be the inspiration for the character. However, the same could not be said about the real Ichabod Crane, who didn't take too kindly that Irving stole his name and then proceeded to peg him as a coward in the fictional tale.

As far as the town of Sleepy Hollow, for years it was called North Tarrytown but in 1996 the town was renamed Sleepy Hollow as a means to attract tourists to the area. Whether the current Sleepy Hollow is the actual town that Irving is describing in his story is debatable and has been for some time. According to Irving's tale, Sleepy Hollow was three miles from Tarrytown along the Hudson River and could be found in "a little valley or rather lap of land among high hills, which is one of the quietest places in the whole world." However, some have disputed that the inspiration behind Irving's Sleepy Hollow, instead, came from Kinderhook, New York where Irving had spent a few weeks in 1809. After all, many of the characters from the story were inspired by real people from Kinderhook. Even President Martin Van Buren got in on the debate, as he believed Kinderhook the place of his birth had to be the place of the fictional Sleepy Hollow of Irving's imagination, instead, of the town which now carries its name.

Then there is the matter of the main antagonist of the story the Headless Horseman. Whether the ghostly horseman was concocted by Irving himself, local tales or even certain European legends remains unknown.The truth behind the apparition remains the most heated debate when it comes to Irving's works. According to Irving, the horseman was once a Hessian soldier who fought and lost his head in an unnamed battle of the Revolutionary War. At the time, there was a tale of such a being who haunted the countryside near the Hudson River. However, another possibility may be found in Germany where Irving spent some time taking in the scenery and the folklore. Irving's Headless Horseman could very well be based off of an old German legend of the Wild Huntsman. The two share similarities as the Wild Huntsman was known to frighten terrified onlookers as he made his nightly rounds with his pack of wild, ghostly hounds. The tale is oddly similar to the Headless Horseman who, also, travels by night on his trusty steed travelling back roads, frightening and killing anyone that he comes across.

Whether the source was in his home country, abroad or just his own active imagination, we may never know. Irving had travelled across Europe and stayed a great deal in England where he met with his literary peers from across not only England but the world. One can imagine that many stories and ideas were shared throughout his time there. It would not be surprising in the least if his source material for his story of the Legend of Sleepy Hollow was actually a mixture of many stories, of many different apparitions throughout Europe and the world.

Whatever the truth is behind Irving's classic tale, the one truth that we can all agree upon is that the Headless Horseman is forever engrained in our imaginations and will haunt the dreams of children and adults for generations to come.


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