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The True Story Behind The Legend of Sleepy Hollow

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 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.

This Post Has 101 Comments

  2. What a wonderful response concerning Sleep Hollow. I also remember the radio shows The Squeaky Door, Inner Sanction, Mr Keen,Tractors of Lost Persons and, if course, the Line Ranger! Happy Memories!

  3. Sleepy Hollow is NOT a fictional place as you state in your summary. Sleepy Hollow is very real & sits right beside Tarrytown.

    1. A quick search of Google Maps and the delightful tales of my teammate have confirmed that Sleepy Hollow is absolutely very real. This has been fixed. Thank you for pointing out the oversight and have a wonderful day! Happy Halloween!

    2. Not real when the story was put to paper. Was deliberately constructed to provide a “real” setting for the story. It is said to be as pristine and peaceful as Irving imagined the town constructed in ink.

  4. I grew up in North Tarrytown (now Sleepy Hollow).

    Sleepy Hollow is NOT a city. It’s simply a small valley in what is now the village of Sleepy Hollow (formerly North Tarrytown).

  6. 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!!

  7. 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

  9. i actually used this story as a reference guide for my English finale. good reference for what i needed to do.

  10. 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

    2. Completely agree with this. I never thought of it as horror. More as lore. And definitely as manipulation of the mind…

      1. I think it started as the Callahan. Then I’ve heard people from the story actually existed. Katrina, Abrham, Ichabod, and the headless hessian cavalryman(I believe someone found actually military reports of a skirmish outside or not far from tarrytown) that his head was carried off by cannonfire. Now as for the rest of the events, I have no idea but if that much of a story were true. I mean come on people, could have happened.

    1. Always loved “the Shadow knows.” Used to listen to it on CBC as youngster growing up. Anybody else?

  15. I want to write a book about this but it’s going to be a modern aged version and with a different story line.

  16. Grew up in sleepy hollow. Going to the graveyard in Halloween was kind of a right of passage.

  17. 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. There’s quite a bit of history to some of those older towns. Thanks for sharing, James!

      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.!!

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

  19. 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.

    2. The guide did not know what he was talking about.

      The first paragraph of the “Legend of Sleepy Hollow” firmly places the story in Tarrytown, NY. No doubt about it.

      “In the bosom of one of those spacious coves which indent the eastern shore of the Hudson, at that broad expansion of the river denominated by the ancient Dutch navigators the Tappan Zee, and where they always prudently shortened sail and implored the protection of Saint Nicholas, there lies a small market town which is generally known by the name of Tarry Town. This name was given by the good housewives of the adjacent country from the inveterate propensity of their husbands to linger about the village tavern on market days. Not far from this village, perhaps about two miles, there is a little valley among high hills which is one of the quietest places in the whole world. A small brook murmurs through it and, with the occasional whistle of a quail or tapping of a woodpecker, is almost the only sound that ever breaks the uniform tranquillity.

      From the listless repose of the place, this sequestered glen has long been known by the name of Sleepy Hollow. ..”

  20. 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

  21. 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.

    2. Why there is an argument is beyond me.

      The first paragraph of the “Legend of Sleepy Hollow” firmly places the story in Tarrytown, NY. No doubt about it.

      “In the bosom of one of those spacious coves which indent the eastern shore of the Hudson, at that broad expansion of the river denominated by the ancient Dutch navigators the Tappan Zee, and where they always prudently shortened sail and implored the protection of Saint Nicholas, there lies a small market town which is generally known by the name of Tarry Town. This name was given by the good housewives of the adjacent country from the inveterate propensity of their husbands to linger about the village tavern on market days. Not far from this village, perhaps about two miles, there is a little valley among high hills which is one of the quietest places in the whole world. A small brook murmurs through it and, with the occasional whistle of a quail or tapping of a woodpecker, is almost the only sound that ever breaks the uniform tranquillity.

      From the listless repose of the place, this sequestered glen has long been known by the name of Sleepy Hollow. ..”

  23. 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

      2. 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. Hey Kevin I’m with you I also wonder if any of these myths could be true ( I guess only the Shadow knows ? ??

        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.

  25. What is written here is very accurate, I was raised in Buffalo NY and we are all the way to and including Pennsylvania, Ohio and New Jersey, “New ENoland States” Somebody needs to study their history and learn where what and why :The 13 Original Colony” came about and also the Hudson River History. Sleep Hallow does exsist, and yes it just outside of Terrytown NY. Both claim and other small communites in the area to be the origin of the legend, which is not uncommon with legends, especially those that involve historical facts such as wars. There are and is 2 great Halloween festivals in each town,Terrytown and Sleepy Hallow, which both cenntralize on the headless hrs Oman and Iccabod Crain. Visit your self have a good time and learn some history before you go. One is American History and the other Legend History in the United States, the s e conditions is harder to locate but trust me it’s thrte, just dedicaite some time before you go, YOU WON’T REGRET IT!!! OH ONE MORE THING SLEEPY HALLOW HAS VERY UNIQUELY CREEPY FEELING AT NIGHT, DON’T WANDEE INTO THE DARK ALONE ,HONESTLY IT’S A VERY UNCOMFORTABLE FEELING!!!!!!

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  29. I’m an aspiring writer and recently started writing a story about a lonesome man and blah blah blah, I grew up in Gillette wyo in a suburban neighborhood that is based off the story. So the community is called Sleepy Hollow and all of the streets were characters from the story and other key words. Anyway I was including that as part of my story so it was really awesome to be able to find out the details behind the story and the place I grew up. Thank you.

    1. I was interested in knowing about Sleepy Hollow and after reading I remembered that I had looked up some of my ancestors and found on my Fathers side of our family my 5 th GreatGrandfather was German Military and a word came up several times. This word was Hessian. Now I know what he was.

  30. I lived in sleepy hollow and I am srry to say but he is real. I saw him with my own two eyes. It made me crap myself. Thats a night I never want to live again.

    2. Hello my name is Emily crane.so many of my friends don’t believe me they say that I lie about the story but I am related to Ichabod Crane he is my great great great grandfather he was chased him a headless horseman any solo with his own two eye so many of my friends don’t believe me they say that I lie about the story but I am related to Ichabod Crane he is my great great great grandfather he was chased him a headless horseman my great grandparents say call me the story when I was just 10 years old I couldn’t believe it if you have any questions about him ask me.

  31. The only inaccuracy that literally jumped out at me was that you described Sleepy Hollow as being the perfect little New England town. Sleepy Hollow is in New York which is not a part of New England. New England consists of Maine, New Hampshire, Vermont, Massachusetts, Connecticut, and Rhode Island

    1. You’re right! Always good to have an army of fact-checkers behind us on these things. I’ll get that corrected. Thanks!

    2. No, you need to understand the history of the
      New England, the largest is new Jersey.
      Hence the name ” 6flags new England.
      There are two. The other one took over Riverside
      Park it was in competition we mountain park , which was the form amusment park in new England. So do your homework, before, showing what you didn’t learn yet.
      At the same time you may be surprised the Springfield MA. Shorten to major wars , the revolutionary, and civil, so do your homework or be reschooled on here.

  32. I as well, love a good scary tale…movie and a book. I loved finding info on scary stories with a truth behind them.thank you for taking time to put this info out there .!

  33. From Derby Connecticut and a person who loves haunted tales and someone who love to find the truth of such stories I enjoyed the story of the headless horseman

  34. You might want to include, in your info, that the real Ichabod Crane is buried on Staten Island, NY. Thank you for all the info. I, too, have always loved the story.

  35. Informative. Did not know that there is a real Ichabod Crane. Dead of course, or is he. Maybe he rides that bridges, wanting his name back. It was fun reading. Thanks.

  36. I’ve been to sleepy hollow many times. It truly lives up to its reputation. I suggest a walk through the cemetery in the fall. Although there is a new bridge see if you can find the original.

  37. Your story is not entirely correct. Sleepy Hollow was the name given by the Dutch a Settlers to the area north of Tarrytown. I grew up in Yonkers NY and now as a freelance writer am writing about the area. They changed the name of the village to North Tarrytown in 1883 and then changed it back in 1996 to it’s original name a Sleepy Hollow.

  38. My mom grew up in a house right next to sleepy hollow park which connects to the sleepy hollow cemetery. She is 73 And graduated from Sleepy Hollow High…. Yes… That’s how her yearbook read.
    I played in that park and walked that bridge. It is as spooky as told but absolutely beautiful in the day.
    I guess what I’m getting at is that when you say “recent years” that North Tarrytown took on that persona kind of bugged me. But I did love reading this.
    Thank you

  41. THANKS SO MUCH FOR THE INFO. I REALLY ENJOYED THE STORIES OF IRVINGS GROWING UP AND TO KNOW THERE IS REALLY A TOWN NAMED SLEEPY HOLLOW

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