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The Legend of Sleepy Hollow...a 200 Year Old Halloween Tradition



Washington Irving, many would say, is the father of the American short story and American literature. He published his first work in 1809 titled A History of New York and from there, published many more stories, biographies of historical figures, and "sketches" of the European countryside that gained him great acclaim. During part of his adult life, he lived in Tarrytown New York. It is here that many say he found inspiration for his most famous short story The Legend of Sleepy Hollow. 2019 marks the 200th anniversary of the publication of Irving's The Sketch Book of Geoffrey Crayon, Gent., in which The Legend of Sleepy Hollow made it debut.


Let's explore though, not only the story, but why it intrigues, haunts, and delights us year after year.


The Legendary Story


You might know Mr. Irving's spooky story from growing up watching the Disney cartoon The Legend of Sleepy Hollow. This is how I was first introduced to our hero, the gangling Ichabod Crane. As the story goes, Ichabod is the school master in the town of Sleepy Hollow New York, located along the scenic Hudson river. From the beginning, we learn that Ichabod is a very imaginative person who also happens to be very superstitious and believes in the supernatural. As the school master, Ichabod travels from farm to farm living with the residents of the town he serves. Because of this, he is frequently riding around the roads of Sleepy Hollow and it is during these rides (especially at night) that he starts to "see" and "hear" things that may or may not be there. We learn that singing Psalms helps ease his mind.


One fine day, Ichabod meets the lovely Katrina Van Tassel; a women he's drawn to not only by her looks, but also by her very wealthy status. Now, there's another man in town just as equally drawn to Ms. Van Tassel, and for the same reasons. His name is Brom Van Brunt. He's sort of the brute type. You know, handsome and very full of himself. The two men fight for the hand of Ms. Van Tassel with each of them taking turns courting her. To both Ichabod and Brom's surprise, Katrina continually chooses Ichabod over Brom. As you might guess, this does not sit well with Brom and the men become enemies.


As it happened, around this time, Mr. Van Tassel, Katrina's father is hosting a party. He invites both Ichabod and Brom to his merry gathering. It was common at these gatherings for guests to tell tales of ghosts, witches, and other supernatural things. Brom, knowing Ichabod's fancy (or gullibility) for the supernatural starts to tell the tale of the headless horseman. It's very likely you know the tale; a Hessian, fighting in the American Revolution had his head cut clean off. Now he rides on his ghostly horse through Sleepy Hollow racing those who ride past the church in town. He chases the poor victim until they reach the bridge. At this, the headless horseman turns into a skeleton and disappears into the night.

Ichabod hungrily took in all the details from Brom's story before heading out into the dark himself to find his way home. It was dark, he was alone, and his imagination was on fire. He rode, on his old horse, down the roads described in Brom's tale. He saw the church and there, upon the very spot it was said he would be, stood the headless horseman holding a flaming pumpkin in his hand. Fearing for his life, Ichabod had his horse galloping faster than it ever had before while the horseman gave chase. Upon seeing the bridge, Ichabod became elated knowing the chase would end soon. But it wasn't to be. The horseman stopped at the bridge and threw his pumpkin at Ichabod. The towns people came to search for their school master the next day, but he was never heard from again.


Why do we love it?


As a short story, The Legend of Sleepy Hollow does a great job of being descriptive; pulling the reader into the world that Ichabod lives in. You can see yourself going down the lane with Ichabod on a clear, beautiful fall afternoon as he heads to the Van Tassel party. In contrast, you can feel the chill from the site of the headless horseman and the breath of his demon horse riding behind you later in the story. Irving does a fantastic job of making the reader feel like they're there.


When I decided to write something about The Legend of Sleepy Hollow, I stopped to think about what makes this story a classic. Why do we return to read it around this time of year? What draws us to it? It could be what I described above. The details in his story make it come alive. Can you see country folk huddled around a fire sipping their cider telling ghost stories? I can. The contrast between our protagonist Ichabod and the antagonist Brom is another way Irving pulls the reader in. Of course we want to root for the scrawny underdog. We hope that he will win the day.


In this particular story however, I think it's the headless horseman that really catches our eye. He's a haunting figure (literally and figuratively) that pulls at our imaginations as much as he did Ichabod's. The reader can put themselves in Ichabod's shoes, knowing just how our imaginations would soar if we rode down a dark country road after midnight. We'd look twice at every shadow, stop to listen at every sound as the memory of Brom's haunting tale echoed through our minds. It's easy to fool ourselves into believing there's a headless horseman lurking around every corner.


Is that the fun we seek when reading The Legend of Sleepy Hollow? Knowing in the back of our minds that a headless ghost with his demon horse and a flaming pumpkin in his hand, couldn't possibly exist; all the while looking for him and the thrilling chill it gives us. Especially this time of year. Halloween is when we seek out this wonderful story the most. We're looking to be spooked and lets face it, a good American ghost story is hard to put down.



More Information


I plan in the near future to make my way to Sleepy Hollow New York and see for myself if the headless horseman makes an appearance. If you're like me, you'll enjoy learning more about the history of Sleepy Hollow and visit the actual sites found in The Legend of Sleepy Hollow.


To learn more about Sleepy Hollow, click here to visit their village website. It's full of fun activities for the whole family!


I hope you have a spooktacular Halloween! Watch out for your head!! Muwahahahahahaha













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