Dark Origins – The Legend of Sleepy Hollow

The Legend of Sleepy Hollow is a gothic story by American author, Washington Irving, and is included in a collection of 34 essays and short stories entitled The Sketch Book of Geoffrey Crayon, Gent.

Cover of The Sketch-Book by Washington Irving from Amazon US

The plot

The Headless Horseman Pursuing Ichabod Crane (1858) by John Quidor

The story is set in 1790 in the countryside around the Dutch settlement of Tarry Town, New York. Sleepy Hollow is a secluded glen which is famous for its ghosts and haunting atmosphere.

Ichabod Crane moves to Sleepy Hollow to be the schoolmaster of the village. As was customary at the time, Ichabod earns practically no money, but is provided with lodgings and food on a rotational basis by the local farmers who are also the fathers of the boys he teachers. This arrangement, and the singing lessons he gives on the side, keeps him employed and also gives him numerous opportunities to listen to the many tales about ghosts, haunted spots and twilight superstitions shared by the farmers wives.

Ichabod is most fascinated by the story of the ghost of the Headless Horseman who is believed to be a Hessian soldier who lost his head when he was hit by a cannon ball during the Revolutionary War. The ghost has been seen riding near the church where he is believed to have been buried.

Katrina Van Tassel is one of Ichabod’s students and the beautiful daughter of one of the most successful of the farmers in the area. Ichabod comes to believe himself in love with her. He sets out to woo her but crosses swords with one of the other men in the village, Brom Van Brunt or Brom Bones. In order to scare off Ichabod, Brom resorts to trying to prank him.

One evening, Ichabod is travelling home late after a party at Katrina’s home. He is confronted by a rider with no head on his shoulders. The head is sitting on the saddle in front of the shadowy man. Ichabod tries to run away and ends up near the church. Ichabod makes a dash for the bridge where the ghost is said to disappear and not follow, but when he looks back, the Horseman throws his detached head at him. It knocks Ichabod off his horse.

Ichabod disappeared leaving nothing behind but hoof prints and a smashed pumpkin. He is never heard from again in Sleepy Hollow.

Origins of the story

Although one of America’s most famous tales and one the resurfaces every Halloween, Irving did not invent the idea of a headless rider. Tales of headless riders existed in Europe during the Middle Ages, including stories by the Grimm Brothers and the Dutch and Irish legend of the “Dullahan” or “Gan Ceann”, a Grim Reaper-like rider who carries his head.

One theory is that Irving’s headless horseman is derived from Sir Walter Scott’s ballad, The Chase, which is a translation of the German author Burger’s The Wild Huntsman.

Another popular theory is that Irving was inspired by the story of the actual Hessian soldier who was decapitated by a cannon ball during the Battle of White Plains around Halloween 1776.

As a teenager, Irving moved with his family to the Tarry Town area due to an outbreak of yellow fever in New York City. The character of Ichabod Crane may have been inspired by Jesse Merwin, a teacher from upstate New York and who was a mutual friend of Irving and Martin van Burden, America’s eighth president. An alternative theory is that Ichabod was based on Samuel Youngs, a lieutenant from Tarry Town and a friend of the Van Tassel family.

Jesse Merwin 1783-1852.jpg
Jesse Merwin, picture credit: https://en.wikipedia.org/wiki/Jesse_Merwin

The name Ichabod Crane belonged to a real army officer, Colonel Ichabod B. Crane who served at Fort Pike during the British-American war of 1812. Irving was also stationed at Fort Pike but there is no evidence that he knew Colonel Crane.

Ichabod B Crane.jpg
colonel Ichabod Crane, picture credit: https://en.wikipedia.org/wiki/Ichabod_Crane_(colonel)

Katrina Van Tassel is also believed to be loosely inspired by Eleanor Van Tassel Brush and, possibly, another woman Irving knew.

About Roberta Eaton Cheadle

I am a South African writer specialising in historical, paranormal and horror novels and short stories. I am an avid reader in these genres and my writing has been influenced by famous authors including Bram Stoker, the Bronte sisters, Amor Towles, Stephen Crane, Enrich Maria Remarque, George Orwell, Stephen King, and Colleen McCullough. 

I was educated at the University of South Africa where I achieved a Bachelor of Accounting Science in 1996 and a Honours Bachelor of Accounting Science in 1997. I was admitted as a member of The South African Institute of Chartered Accountants in 2000. 

I have worked in corporate finance from 2001 until the present date and have written seven publications relating to investing in Africa. I have won several awards over my twenty year career in the category of Transactional Support Services.

I have been published a number of anthologies and have two published YA books, While the Bombs Fell and Through the Nethergate. I have recently published my first adult novel called A Ghost and His Gold which is partly set in South Africa during the Second Anglo Boer War.

Find Roberta Eaton Cheadle

Blog: https://wordpress.com/view/robertawrites235681907.wordpress.com

Twitter: https://twitter.com/RobertaEaton17

Facebook: https://www.facebook.com/robertawrites

Amazon: https://www.amazon.com/Roberta-Eaton-Cheadle/e/B08RSNJQZ5

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34 Comments on “Dark Origins – The Legend of Sleepy Hollow”

  1. Hi Kaye, thank you for hosting this post today. I thought this history was very interesting. This story is not as well known in Europe as it is in the USA.

    Liked by 1 person

  2. Joan Hall says:

    I learned something new today, Robbie. I never knew there really was an Ichabod Crane. The Legend of Sleepy Hollow is, of course, a classic. I might have to read it again after seeing this post.

    Liked by 2 people

  3. Staci Troilo says:

    I was always fascinated by this story. Thanks for sharing the details about it here.

    Liked by 2 people

  4. Jim Borden says:

    thanks for the background; I’m familiar with the tale, so it was nice to have the story placed in some context…

    Liked by 2 people

  5. Fascinating history about this tale. I wonder if he ever imagined how famous/popular this story would become, considering its macabre theme.

    Liked by 2 people

  6. Fascinating, Robbie! I remember this story well, but learned so much more about it today… Thanks!

    Liked by 2 people

  7. This is one of my favorite Halloween stories, Robbie. ❤

    Liked by 2 people

  8. Fascinating story Robbie, and while I have seen the film some time ago, had no idea of its origins…. I thought it purely fictional and not based around some facts…
    Loved reading… Thank you ❤

    Liked by 2 people

  9. petespringerauthor says:

    Like others, I had heard parts of this story before. I’m somewhat amused by the lengths that the competitor went to get rid of Ichabod. Perhaps he was never the wiser. Or maybe, it happened again when Ichabod was pursuing another woman. “No, not the old headless horsemen routine again!”🤣

    Liked by 2 people

  10. I didn’t realize that Ichabod Crane was the name of an actual Army officer. It’s such a great name! My niece lives in the next town over from Tarry Town in New York. The town make a very big deal of it Sleepy Hollow connection to attract the tourists. 😉

    Liked by 2 people

  11. Mae Clair says:

    This was such a fascinating post, Robbie. Much of this I knew but other parts were true eye-openers. I loved how you delved into the origins of this story.

    Liked by 2 people

  12. memadtwo says:

    It makes sense that the inspiration came from both legend and the authors experience. The headless horseman is a motif I’ve seen in other paintings of the time, often combined with th grim reaper.

    Liked by 1 person

  13. Bowling for Cranes… Yes, ma’am death gets everyone one way or another.

    Liked by 2 people

  14. markbierman says:

    I was always fascinated by this macabre tale, but I had no idea it originated in Europe. But that’s no real surprise.

    Liked by 2 people


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