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Week Thirty Nine

The Legend of Sleepy Hollow


Week 39 means we're 3/4 of the way through this 52 week long project! Let's celebrate with our final spooky October story just in time for Halloween. You definitely know the ghost in this one.



The Facts

Text: The Legend of Sleepy Hollow Author: Washington Irving

Genre: Ghost story, Gothic fiction, American lit Year: 1819

Available: Public Domain, Free Here


Content Warning: Some outdated/period typical language used to describe Black characters.


The Fiction

There is one classic ghost who seems to pop up every Halloween. He is one of the most famous ghosts in our pop culture imagination and one of the most enduring. This week let's ride alongside The Headless Horseman from Washington Irving's American classic: The Legend of Sleepy Hollow.


Like last week's story, The Call of Cthulhu, this week we have another long short story, but it's such a Halloween classic I couldn't not write it about. This story is all over our pop culture from paintings, to even US postage stamps as shown in this week's image. There have been many film and television adaptations of The Legend of Sleepy Hollow, and the headless Horseman is an iconic character, depicted often as a larger than life figure on his black steed with a jack-o-lantern for a head. Where did the jack-o-lantern come from? I'm not entirely sure, as it isn't exactly in the original. We'll just have to dive into the source of this iconic Halloween classic to find out.


The Legend of Sleepy Hollow is a verbose short story, full of lengthy descriptions of the community of Sleepy Hollow, the backstory of Ichabod Crane, our protagonist, background on a love triangle, lots of descriptions of nature, and eventually we get to the actual ghost part.


In summary Sleepy Hollow is a community by the Hudson settled by the Dutch. The narrator notes that there is something about Sleepy Hollow that seems to attract and induce fantastical imaginations and spirituality. There is something about this place and the people who live there that makes legends and ghost stories thrive. The most famous of these stories is of course the Headless Horseman, the ghost of a German solider whose head was said to have been blown off by a cannon ball in battle and whom many people have had encounters with. One member of this community who loves, but is also frightened of these stores, is schoolmaster/teacher Ichabod Crane.


We learn that Ichabod has fallen in love with Katerina Van Tassel, an hieress to one of the most sucessful estates in the community. Katrina is a bit of a flirt, a "coquette" as this story calls her. She is beautiful and heir to an immense fortune so every man in the village seems to want her. It seems to come down to two men vying for her hand: our Ichabod Crane, and Brom Bones the original jock/popular guy rival. Brom is an athletic man noted for his skilled horsemanship, and while not genuinely cruel he is also known for his streak of mischief.


The main action of the story takes place one Autumn night, when Ichabod gets invited to a party at the Van Tassel estate. There he dances with Katrina, and enjoys the wealth and comfort of her home, imagining it all one day being his. Brom Bones is said to be looking on with jealousy in a corner. Ichabod spends the night hearing and telling ghost stories with the other party guests, the most popular of these stories being encounters with the Headless Horseman.


The narrator admits they don't know what happened next exactly but that when the party was ending Ichabod stayed late to have a word with Katrina and something seemed to happen between them because Ichabod was seen leaving the party in a desolate rush. When riding home on his borrowed horse, Ichabod comes across the bridge where famous Headless Horseman sightings have happened. He beings to hear strange noises and is unsure if it is just the wind. A figure on horseback appears next to him. He attempts to ride away from the figure, but the figure follows. When he slows down, the horseman next to him slows down.


Eventually light from the moon shines on the figure next to him and to his horror Ichabod realizes the rider has no head on his neck, but is holding it cradled in his lap! He flees, his horse running off in a panic while he spurs it on and the Headless Horseman gives chase. Ichabod's saddle comes undone and he struggles to remain on the horse while fleeing towards the church where legends say the Horseman usually vanishes. When he is near the church he sees the horseman raise his head, and throw it. The severed head collides with his own and Ichabod is knocked off the horse unconscious.


The next the day the community begins to get worried when there is no sign of Ichabod Crane returning home or showing up to teach at the school. They find the horse, the broken saddle, and strangely, a smashed pumpkin by the old church but no Crane. He never returns, and eventually the community gets a new school master.


The narrator notes that Katrina married Brum Bones, they also note that Brum always seemed amused when people told the story of Ichabod and the Horseman, especially the detail with the pumpkin. One farmer claimed years later to have run into Ichabod Crane alive and well in New York. After being apparently spurned by Katrina Van Tassel and his fright from the horseman it is thought Ichabod might have taken the opportunity to flee and start a new life, with the farmer who saw him claiming he had become a lawyer and then a judge in New York. The narrator notes that still the wives of Sleepy Hollow tell the story of Ichabod Crane and believe he was carried off by some supernatural force that night.


Some versions of the story end with a post script where the narrator talks about the conference where he first heard the legend of Sleepy Hollow. The first version I read for this post did not include this post script, but the version linked above does. In the post-script the man who told our narrator the story claims that he doesn't believe even half of it happened.


The Feeling


So there isn't a jack-o-lantern in the original Legend of Sleepy Hollow but there is a pumpkin. I remember when I first read this story a few a years ago (with the post script I might add)I felt kind of disappointed. This was one of the most famous American ghost stories? But it seems so obvious what happened. Ichabod is described as a superstitious man, his rival in love, Brum, is known as a great horseman, the pumpkin was the 'head' that him, and someone even said they saw him alive years later. There is some ambiguity for the reader, maybe Ichabod Crane really was spirited away (ha) by the real Headless Horseman, or maybe as much of the evidence implies this is a love story gone wrong dressed up as a gothic ghost tale.


Reading it this second time for this week's blog post I wasn't as disappointed in the ambiguity/possibility in the nature of the Headless Horseman. I think there is enough room for people to believe what they like. Also I like the fact that , if Brum Bones is the Headless Horseman, than this is sort of a Scooby-Doo story. Someone using an urban legend to scare someone else away and get what they want, that's classic Scooby-doo stuff.


Irving does not worry about wasting letters when describing Sleepy Hollow. As I mentioned above this is a long story, but really until the night of that party not a lot actually happens. A large part of this text is the narrator setting up backstory and atmosphere by describing the village and the community. It definitely isn't the sort of thing you see a lot of in modern fiction, what with those shrinking attention spans, but if you can stick with it the text is full of some vivid and beautiful descriptions. Sleepy Hollow is charming, full of colour, and good food, and life. It almost reminds me a little of how Tolkien describes the Shire in his Middle-Earth books; there is something quaint and yet also very close to paradise in the lush descriptions of this community.


I also like that, while the fact of whether Ichabod Crane met the real Headless Horseman is left up in the air, there is still some great supernatural content in this story. The way that Sleepy Hollow is described as a town which attracts and encourages fantastical and supernatural fancies among its residents is such a cool detail. It brings to mind the modern supernatural story trend of the spooky small-town or hellmouth that draws supernatural creatures. This is a trope we see all over our pop culture now (Buffy the Vampire Slayer, Gravity Falls, Welcome to Nightvale, King Falls AM, Starkid's Hatchetfield musicals, Twin Peaks, etc). I wonder if Sleepy Hollow is something of the origin of this trope. It seems at least to be a sort of ancestor to it. A town where if the supernatural isn't attracted, than stories about it at least very much are.

The autumn vibes are very present in this story. That along with the pumpkin, later turned into a jack-o-lantern through some sort of pop culture osmosis means I can see why this story is considered a Halloween classic.


Which brings us to the star of the show, not Ichabod Crane, but our ghost with the most, The Headless Horseman. What is it about that guy that titillates and scares us? Well headless ghosts, and even headless horsemen/soldiers were pretty popular folktales in Europe. The horseman is said to be roaming the land looking for the head he lost in battle. Its a good and understandable reason for why a ghost is hanging around. So there's some classic folklore being used as the foundation for this story.


There's also something, I don't know, fun about the Headless Horseman in this story. The stories we hear about him before his appearance are spooky but never really harmful. One man tells a story about the horseman turning into a skeleton and throwing him in a river. Brum Bones himself claims to have encountered the horseman and challenged him to a race, which the horseman accepts? Which is just hilarious and very funny to think about this ghost just having fun and racing random passersby because they asked. Other than the last encounter with possibly the horseman, where he throws his "head" at and possibly kills Ichabod Crane, he's never really described with any kind of malice or danger, which makes him a fun legend to talk about.


Also the giant horse and flaming jack-o-lantern thing in modern adaptations is pretty wicked.


Whether you believe that Ichabod had a real supernatural encounter or just ran-off his rival in a costume Sleepy Hollow is an excellent Halloween story. Either the ghost was real, or someone dressed up as a ghost to scare someone. In both interpretations the story really captures the Halloween spirit.


Happy Halloween! Read something scary!


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