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The Tale of Sleepy Hollow and the Headless Horseman (and the Real Town of Sleepy Hollow!)

Updated on August 8, 2013
kittythedreamer profile image

Kitty has had paranormal experiences her entire life. These experiences have fueled her passion to write about all things supernatural.

The Headless Horseman of Sleepy Hollow

As a child, my stepfather told me the eerie tale of Ichabod Crane and the Headless Horseman. Admittedly, it/ scared the living daylights out of me! Every time I heard a frog croak or the wind howl outside of my window, I thought that the headless horseman was coming for my head! If you have never heard Washington Irving's The Legend of Sleepy Hollow, you are truly missing out on a spine-tingling American classic.

In a glen of Tarry Town, New York, known as Sleepy Hollow, Dutch settlers seem to be under a witch's spell...some say that it is due to one of the glen's original residents, a "high German doctor", others say it is of a Native witchdoctor's doing. Whomever caused this spell to settle over the land of this small rural town at a point of the Poncatico River in New York, it is present nevertheless and has been witnessed by all whom have come to visit Sleepy Hollow. Many of the townsfolk have heard and seen strange things, which are believed by the town's outsiders to be hallucinations caused by a curse or other more logical explanations. The most infamous and twisted tale whispered throughout the town of Sleepy Hollow is that of a headless horsemen, thought to be a Hessian ghost who had his head taken off by a canon ball during the Revolutionary War.

This headless Hessian rides a dark horse and has been seen by numerous townfolks, stalking the woods of Sleepy Hollow at night and seen riding particularly close and towards the town's church graveyard. Many say that the headless horseman's body is buried in the Sleepy Hollow Church's graveyard and the reason he is out riding the forest is to look for his missing head.

A man by the name of Ichabod Crane lived in the glen of Sleepy Hollow and had come from the state of Connecticut in order to educate the children of the haunted town. With such a strong name, one would imagine a strong and strapping man; however, Ichabod was quite the opposite. He was tall and lanky, very much resembling Shaggy from Scooby Doo. Irving describes Ichabod Crane as having "feet that could be shovels" and hands that "hang down way past his sleeves", with "protruding eyes". Poor fella.

Ichabod ends up falling for one of his pupils, Katrina Van Tassel, who was a sexy young maiden of eighteen. Unfortunately, Ichabod had some competition in the hand of Katrina...his competition was a strapping, masculine lad by the name of "Brom Bones." The story thickens when Ichabod attends a gathering at the Van Tassel's, arriving to Brom being the "hero" of the scene. Somehow, Ichabod's quiet yet persistent ways won a dance with Katrina Van Tassel and left Brom sulking in a corner of the party.

On Ichabod's dark journey home, through the thick woods of Sleepy Hollow and towards the old covered bridge...he meets a dark specter. The dark specter is riding on a dark and strong-framed horse, keeping up with Ichabod's horse's steps right beside him. Ichabod decides at first to ignore the man by singing a tune and casually walking towards the bridge leading to the Sleepy Hollow Church, but the specter begins to chase Ichabod and Ichabod realizes in a moment of fear that the specter on the horse had no head! The pursuer chases Ichabod, Ichabod loses his saddle and makes it to the Sleepy Hollow covered bridge...but alas! Poor Ichabod was never seen or heard from again after this fateful night.

Many of the Sleepy Hollow townsfolk believed that Ichabod Crane was taken by the Headless Horseman and that he haunts his old schoolhouse in the glen. Others claimed that Brom Bones, who acquired Katrina's hand in marriage, was to blame for Ichabod's disappearance. No one in Sleepy Hollow ever found the body...just evidence that there had been a struggle and that Ichabod had lost his hat amongst the struggle for his life.

Though this Sleepy Hollow story is a work of fiction, cleverly composed by Washington Irving, the legend lives on throughout the United States and is one that is still told in a whisper around bonfires in the town of Sleepy Hollow today.


The Real Sleepy Hollow

One might be surprised to discover that The Legend of Sleepy Hollow was based on a real town in New York that is still standing and thriving today! Washington Irving resided in the town of Sleepy Hollow and no doubt acquired his inspiration for the story from real legends known to the townsfolk. The town of Sleepy Hollow is fairly small and is about 30 minutes north of Manhattan, nearby Tarry Town. It is a quaint little village with happy families occupying the homes.

Unfortunately, Sleepy Hollow's old covered bridge that is so famous from the Legend, has been paved over into a common road, though there is a historical marker showing exactly where the infamous bridge once stood. The Phillipsburg Manor house and property is available for tours and gives one a slice of the 1700' could get literally sucked back into the time of the Hessian Headless Horseman. The Sleepy Hollow Church and its spooky cemetery can be visited, as well, and remains the same as it did during Washington Irving's time in Sleepy Hollow.

The next time you are in the New York City area, take a trip up to Sleepy Hollow and visit the sites. Be careful that you don't get bewitched by the town's haunting energies...oh, and don't lose your head!


Submit a Comment

  • kittythedreamer profile imageAUTHOR

    Kitty Fields 

    7 years ago from Summerland

    Good point, Just History. Thanks for reading and commenting. :)

  • Just History profile image

    Just History 

    7 years ago from England

    The name sleepy hollow just tells you that it is anything but.... I have never managed to see the film, too scared I guess, but it is interesting that it was based on a real place. Did Irving realise that with all his literary and dramatic skills he could not invent a better name?

  • kittythedreamer profile imageAUTHOR

    Kitty Fields 

    7 years ago from Summerland

    Hi, ruffridyer! You are one hundred percent right about that my friend! Thanks for stopping by.

  • profile image


    7 years ago from Dayton, ohio

    These old tales never lose there charm.

  • kittythedreamer profile imageAUTHOR

    Kitty Fields 

    7 years ago from Summerland

    Jeff - I loved it, actually! It's probably my most favorite Johnny Depp movie (next to Pirates, of course). And Christina Ricci was nothing short of perfect as Katrina Van Tassel!

    Fay - thanks for reading another one of my hubs! It's good to know that people are enjoying what they're reading and I appreciate your compliments very much! The movie Sleepy Hollow has been out on DVD for years...try to rent it, if you like horror flicks and Johnny'll probably like that movie too. :)

  • profile image

    Fay Paxton 

    7 years ago

    Very enjoyable read. Thanks for giving me the background to that old haunting tale. I'll have to keep an eye out for the movie. I like Johnny Depp.

    up/useful and awesome

  • Jeff Berndt profile image

    Jeff Berndt 

    7 years ago from Southeast Michigan

    Another enjoyable read. Out of curiosity, what did you think of the Tim Burton Sleepy Hollow movie?

  • kittythedreamer profile imageAUTHOR

    Kitty Fields 

    7 years ago from Summerland

    Hi, Latasha! I liked Sleepy Hollow with Johnny Depp, as well. Though there were some wanderings away from the story, there were many things that remained true to Irving's original work. Thanks for your support!

  • Latasha Woods profile image

    Latasha Woods 

    7 years ago from USA

    Great story. I really enjoyed the film adaptation of the "Sleepy Hollow" legend. Thanks for sharing!!

  • kittythedreamer profile imageAUTHOR

    Kitty Fields 

    7 years ago from Summerland

    hey, dahogluned. glad you liked it. :)

    will starr - too cool! i too am enchanted with covered bridges as my grandparents and i used to visit one particular covered bridge in dushore, pennsylvania when i was a child. it definitely ties into the memory of this scary story. so glad you enjoyed. thank you for stopping by.

  • WillStarr profile image


    7 years ago from Phoenix, Arizona

    Last summer, I attended a class reunion in Iowa, and on the way back to Arizona, we stopped in Madison county and visited the covered bridges.

    The cool, dark interiors were more than a little spooky for some reason, and now I know why. As a boy, I was spellbound the tale, and the old memory was still there, all those years later.

    Great Hub!

  • dahoglund profile image

    Don A. Hoglund 

    7 years ago from Wisconsin Rapids

    Nice background on an old legend brought to us all by Washington Irving.


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