The True Story Behind The Legend of Sleepy Hollow - Quicken Loans Zing BlogI have always loved scary stories. From watching Scooby Doo religously every afternoon at my grandma’s house to reading my first horror novel (“It” by Stephen King) when I was in 4th grade, I was born a connoisseur of the frightening. I remember one of the most interesting and terrifying stories to me was The Legend of Sleepy Hollow. My first exposure to it was through the Disney movie “The Adventures of Icabod and Mr. Toad” – a movie that was one half “The Wind in the Willows” and one half “The Legend of Sleepy Hollow.”

Through the silly, soft lens of Walt Disney, that version wasn’t nearly as horrifying as later adaptations, but it sparked some kind of real fear in me as a child – and I loved it.

Everyone knows the story of The Legend of Sleepy Hollow with its tale of Ichabod Crane the slight, yet smart, schoolteacher, and the menacing Headless Horseman. But I wonder how many people know that  its author, Washington Irving, drew inspiration from real-life events that took place in and around Tarrytown, New York.

The story takes place in the late 1700s in a fictional city called “Sleepy Hollow” which is near Tarrytown, New York. A school teacher by the name of Ichabod Crane comes to town from Connecticut and finds himself at odds with a local by the name of Abraham “Brom Bones” Van Brunt over a woman named Katrina. Meanwhile, the ghost of a soldier who lost his head to a cannonball during the American Revolution haunts the area every night in search for his missing head. And should anyone interrupt the Headless Horseman on his quest to find his head, they are killed. One night, as he was leaving a party at Katrina’s home, Ichabod found himself face-to-face (so to speak) with the Horseman, never to be heard from again.

The Hudson River Valley, where Tarrytown is located, has a large Dutch population and much of that ‘old country’ folklore  finds its way into the stories of Washington Irving. In fact,  there is a German legend of the Headless Horseman that has been said to influence the Dutch tales. In one tale, he’s called “The Wild Huntsman” who chases people who have committed terrible crimes through the woods at breakneck speeds.

Irving writes in the story that there is a bridge near an Old Dutch Burying Ground where, legend has it, that if the Horseman attempts to cross it, he will disappear in a great “flash of fire and brimstone.” However, it proves to be not the case as the Horseman races across the bridge and throws his decapitated head at Ichabod. What happens next, is a mystery, but Irving writes that the old Dutch wives will tell the tales and create the legend that Ichabod was “spirited away by supernatural means.”

In reality, the late 1700, near the end of the Revolutionary War, the Hudson River Valley area was equivalent to the wild west – an area of law breakers and law makers, rife with rivalries and fighting between British loyalists and American raiders. Also, the area was known for its abundance of Hessian Jagers – German mercenaries who were contracted by the British Empire to serve  during the American Revolutionary War. These Hessians, in addition to being known for their ruthlessness, were also known for their sharpshooting and horsemanship skills.


The area residents, who, as I mentioned, were predominately Dutch settlers, did not care much for these German mercenaries and told the tales of the ruthless German horsemen who killed without discretion. At one point, a headless corpse of a Hessian soldier was found in the area and later buried by a local family in an unmarked grave in the Old Dutch Burying Ground.

But what about Ichabod Crane? There was an acutal Ichabod Crane who was a military man  – a Marine and an Army officer – who served in the War of 1812. Washington Irving met the real Crane at Fort Pike in Sackett’s Harbor, New York in 1814 and was immediately inspired by his name and character. Although, the soldier was nothing like his namesake school teacher.

However, the mannerisms and the behavior of Ichabod Crane are said to be inspired by a friend of Irving’s from Kinderhook, New York. The teacher, Jesse Merwin, was originally from Connecticut and moved to Kinderhook to teach school. Unlike Major Crane, Mr. Merwin was proud of his association with the story.

One of the most interesting things I’ve discovered about the story of Sleepy Hollow is that the town itself wasn’t an actual place until just recently. Well, the location existed, just not in name.  In the story, Irving states Sleepy Hollow is “perhaps about three miles” from Tarrytown in “a little valley or rather lap of land among high hills, which is one of the quietest places in the whole world.” The village of North Tarrytown has claimed to be the inspiration for the story for as long as the story has been written, however, many believe that Irving based his story on Kinderhook, where he met his friend Jesse Merwin. It wasn’ t until 1996 when the North Tarrytown officially adopted the name Sleepy Hollow in honor of the story.

It’s in Sleepy Hollow Cemetery where Washington Irving is buried along with other famous names like Andrew Carnegie, Walter P. Chrysler, Brooke Astor and Elizabeth Arden.

Not that long ago, I took a trip to New York and stayed in Tarrytown. Our first stop was Sleepy Hollow and it’s every bit as perfect as you’d imagine it to be from the story. At first sight, it’s a beautiful and postcard-perfect New York town that feels like an ancient forest growing in the hills. But at night, the picturesque facade drops and every face becomes ominous, every noise becomes a bellow, nothing is what it seems. The night is darker and you feel like someone or something is just waiting two steps behind you.

It’s not that difficult to imagine or to understand just how Washington Irving found such profound inspiration for one of America’s most horrifying tales in such a small and beautiful town.

Related Posts

This Post Has 87 Comments

  1. Loved this, always have.
    This is truly a classic that will live forever. Its great story’s like this and cartoons like Scooby Doo, that feed the imaginations of generations.
    Thanks for sharing this!!

  2. I wonder if the tale could be told with both towns in mind which only adds to the profoundness and mystery this story has place one us threw the years. There is no doubt that the story is a mix of both mens lifes as he both has the air of a soldier and the intellect of a teacher. I beliece that was the author intention, as the teacher above has stated the story is not a “scary” story if you truely read it, it is a lite hearted jest on the supernatural of the story and the peoples believes of such a story’s truths so why would he not also add to the jest but creating a underlying mystery of who and where by mixing and matching? To me it is brilliant and thus why the story has headle strong for all these years

  3. I routinely assign my students The Legend of Sleepy Hollow, along with a glossary I created to aid them through the often archaic language. This 49-page story has generated a 200-word glossary! The vocabulary is sometimes daunting to my students, but also immensely valuable for increasing their overall English skills. Conquering this short story allows them to approach other classical literature with more confidence, and increases the vocabulary they’ll be able to use in their writing (and, maybe, one hopes, in their speaking).

    One thing with which I take issue is the notion that this book is a horror story. I’ve read it many times, and believe it’s a satire set against, and using the superstitions of, the region. Even though I’ve read it countless times, certain parts still make me laugh out loud! As I see it, the ‘legend’ is used by Brom Bones to cleverly manipulate Ichabod’s fears. Brom both one-ups Ichabod (as Ichabod fancies himself the smarter and wholly better of the two), and eliminates him as the nuisance he’s become to Katrina. The successful outcome of this charade is that Ichabod leaves Sleepy Hollow forever after his encounter with the “Headless Horseman.” I don’t believe Brom ever viewed Ichabod as any sort of plausible romantic rival. Eventually, he finds a way to just shoo him away, by riding his horse wearing a costume and pumpkin on his head! Ichabod’s absurd and pathetic notion of a happily-ever-after with Katrina was only ever in his fervid imagination. I know, I know, a guy can dream…

    Irving is making fun of superstition, he’s making fun of the sort of person Ichabod is. It’s good-hearted, and definitely comical. I love it!

    Sorry, don’t mean to rain on the parade for all who love what they see as the horror aspect, but understand that aspect comes mostly from Hollywood, not Washington Irving. Scary movies make more money than satires, so Hollywood has always focused on the “scary” elements of The Legend of Sleepy Hollow.

        1. Hi Christophe:

          We’re talking about a fictional tale that has origins in various cultures, so I think it’s hard to judge right or wrong. Tarrytown is a three minute drive from Sleepy Hollow and Washington Irving lived and is buried there. We’re talking about the American version of the tale which is very much wrapped up in Irving’s story

  4. I went to NY about 40 years ago for
    some work related things. Took the wife and traveled on two weekends.
    I swear we went to Sleepy Hollow and the name was on the established at sign. I remember because it said 1650 something. Most towns where I live were established In the 1800’s.

      1. Good Luck Kalin! Washington Irving is a tough act to follow, but give it a try. Who knows, you may come up with a great horror story of your own….Freddie K.!!

  5. Sleepy Hollow was a class trip anelementary school will never forget the experience I would love to return back

  6. Great story. On a historic walking tour in the town of Basking Ridge, New Jersey, the tour guide mentioned the the story of the headless horseman originated there.

    I’m starting my research, and would be interested what other towns you noted lay claim to the origination of this tale. Will be back in touch when I complete my research.

  7. Every time I watch sleepy hollow I wished I visited when I was a new Yorker. The show is very intriguing and I only wish the lieutenant was never removed it seems less authenticated without her

  8. Sooo….I went to Ichabod Crane Elementary. Surprisingly it’s in Kinderhook NY. Washington Irving wrote the story set in Kinderhook. The argument where it originated goes back a long time with other places insisting it’s them, but look up Kinderhook. It’s kind of interesting.

    1. We won’t take sides in the Sleepy Hollow debate, J, but it is really interesting to see all the history behind the region.

  9. dear people
    I am Gregory Wray I have always wanted to visit sleepy hollow I enjoyed the legend of sleepy hollow I never knew that sleepy hollow actually existed I thought it was a made up name until I located it on the map of new York it really fastenated me and still does
    I am 54 about to turn 55 but neat places always thrilled me I used to live in Pennsylvania
    but me and my wife divorced before I could visit sleepy hollow
    well there is another town I thought was made up Transylvania and its a real town too
    stuff like this always hits with me

      1. I lived in Germany as a child in the early 80s. We traveled all over Europe and visited many castles. I’ve seen Frankenstein castle and draculas castle as well. An interesting fact, the Cinderella castle at Disney world is modeled after a castle in Germany called nueswanstein ( not sure of the spelling).

        1. “Only The Shadow Knows” Oh my Gosh! I remember being little and hearing that! But I can’t remember exactly where it’s from? Thank you bringing that memory back for me.

1 2

Leave a Reply

Your email address will not be published. Required fields are marked *