Classic Horror

Classic Horror: The Legend of Sleepy hollow

Headless horseman for the win

Today I am writing to talk to you about the Legend of Sleepy Hollow.

Sleepy Hollow is a short story written by Washington Irving in 1820 and I imagine most of you will be familiar with the story even if you have not had the opportunity to read the original short.

The story follows Ichabod Crane, a meek man, as he contends with the local bully Brom Bones for the hand of the beautiful Katrina Van Tassel.

This story has been adapted time and time again, it’s been television series, it’s been a play, it’s been movies, and it’s been animated by Disney. It is almost impossible not to know this story in one iteration or another.  


Photo by Luca Chiandoni on

Set in 1790 in Sleepy hollow, which is renowned for its ghost stories, we meet Ichabod Crane, a school master who has come to Sleepy Hollow. During his stay he assists with light farm work and looking after young children while also being the school master. While being meek, he is also superstitious, helpful, and overall pleasant. He is popular with the ladies and a fan of their gossip and ghost stories.

He falls for Katrina Van Tassel, the young daughter of the wealthy Baltus Van Tassel and must compete with the local hero/bully Brom for her hand. Brom, who is unable to force Ichabod into a physical confrontation decides to try and scar him away from the town with pranks, as he is aware of how superstitious Ichabod is.

Eventually, Crane attends a harvest party at the Van Tassels home and Brom uses it as an opportunity to tell the story of the Headless Horseman. Ichabod also wishes to propose to Katrina, but this doesn’t quite work out. He leaves the party and is freaking himself out on the journey home (due to Brom’s stories and his own active imagination). Ichabod then encounters a cloaked rider at an intersection. He is freaked out by the rider’s size and silence and the fact he doesn’t appear to have a head; well, he does but it’s on his saddle not his shoulders.

Ichabod immediately does a runner and tries to get to the local bridge which is where the headless horseman is supposed to vanish according to the stories. Ichabod does make it across the bridge but when he turns to see what has become of his ghostly pursuer the horseman lobs his head at Ichabod and knocks him off his horse.

The following morning Ichabod has mysteriously vanished, all that’s left is his hat, his horses saddle, and a smashed pumpkin. Katrina later marries Brom, who gets a very knowing look in his eye whenever anyone mentions Ichabod and his mysterious disappearance.

The story leaves it vague as to Ichabod’s fate, it is strongly hinted that the rider was Brom trying to scare Ichabod off but never outright confirmed. It is also not confirmed if the blow to the head killed Ichabod or if he got up and fled.

My Thoughts

Photo by Lisa on

Like with a lot of classic horror I am a fan of The Legend of Sleepy Hollow. I love how so much is left up to the reader, is the horseman rea? Or just a local Legend? Was Ichabod murdered by Brom? Or did he simply run away? Did Katrina marry a murderer?

While the short story was not my first experience of this story, I think my first experience was the Disney animated short when I was young, followed up by the Film version by Tim Burton. I was surprised with just how different the story was from the Tim Burton version and for a long time I preferred the film as it took out the ambiguity and flat out showed you that the horseman was not only real but also killing people. But then I’m also a fan of Tim Burton’s very distinctive style so that probably had a lot to do with it (off topic but watch Frankenweenie, the stop motion version, its very cool).

But as I read and re-read the short story I got to better understand the true horror of this story. It’s not in ghosts but in people. The fact that Brom was willing to either terrify a man into fleeing a town or outright kill him plays on the fact that while we make up stories of monster’s to better understand the world around us, people are always more monstrous. This story plays on our fear of monsters, never quite confirming if they are real but hinting that even if they aren’t then there are monstrous people who are easily worse.

Brom is not the only potential monster in this story, Ichabod himself could also be considered monstrous, it is heavily hinted that his pursuit of the young Katrina is not because of love but very much because of her father’s wealth and the fact that a marriage to her would cement Ichabod more firmly in the community. While it wouldn’t be the first marriage to take place due to motivations aide from love, it does not paint Ichabod in a favourable light.

The atmosphere of the story is wonderfully classic, true gothic with its spooky settings, and bone chilling characters and ghosts.

Overall, I would strongly recommend this story, it’s a short little ditty but one well worth your time.

2 thoughts on “Classic Horror: The Legend of Sleepy hollow”

  1. I’ve always enjoyed this story. The Disney and Tim Burton films were both excellent. As a kid, I always hated that Brom got the girl, but in later years I’ve come to see Ichabod’s negative qualities more and more, and Katrina’s too (though later adaptations made him more heroic and fanfiction/sequels redeem him as he seeks revenge). Still, if it was Brom (and I think it was), his efforts were really in vain given that Katrina had already rejected Ichabod.

    I highly recommend this song that came out this year in honor of the story’s 200th anniversary, composed and sung by Kristen Lawrence (whose specialty is Halloween carols):

    1. It is a great story, like you my views on the characters changed a bit as I got older. Now they’re all a bit shit and I love it, give me more flawed characters, booya.

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