Pondering the Mystery: The Legend of Sleepy Hollow

“To see him striding along the profile of a hill on a windy day, with his clothes bagging and fluttering about him, one might have mistaken him for the genius of famine descending upon the earth, or some scarecrow eloped from a corn-field” – Washington Irving, “The Legend of Sleepy Hollow

There are a handful of stories I feel a physical need to revisit frequently, especially when the leaves start falling in autumn. At the top of that list is “The Legend of Sleepy Hollow” by Washington Irving. I first encountered the tale, as I am sure many people did, from Disney’s The Adventures of Ichabod and Mr. Toad (1949), which, in my humble opinion, remains the most accurate to the original story among the other adaptations. As an almost-27-year-old, I still watch the Disney version all the time. My love of that cartoon and its whimsical protagonist led me to seek out a copy of the source material at a young age. No matter how many times I read this story, listen to the audiobooks, or watch one of its many cinematic adaptations, the same question gallops through my mind:

What happened to Ichabod Crane?

This classic story by Washington Irving has enchanted readers and fans of horror for the 200 years since it was published. Just in case, here is an overview: Ichabod Crane, an academic from Connecticut with an enhanced fear of the supernatural, travels to Sleepy Hollow (Tarrytown, New York) to become the new schoolmaster for the underprivileged Sleepy Hollow children. Most of the village’s inhabitants find Ichabod fascinating and charming. He catches the eye of Katrina Van Tassel, the daughter and only child of the wealthy Baltus Van Tassel. Brom Van Brunt, a.k.a. Brom Bones, has his heart set on Katrina himself, and he does not take kindly to her and Ichabod’s growing connection. At Baltus Van Tassel’s annual harvest celebration at his estate on Halloween Night, Brom shares the story of The Headless Horseman in an effort to frighten Ichabod on his travels home. According to the legend, the Headless Horseman was a Hessian soldier who came to the American colonies during the Revolutionary War and lost his head to a cannonball. As a result, he haunts Sleepy Hollow in search of a new head, which he would sever from victims with the sword he carries. With his mind full of the night’s tales, Ichabod journeys home in fear of every sound and movement around him. To his despair, he is soon joined by what appears to be the spirit of the Headless Horseman. After a thrilling chase, the sun rises on Sleepy Hollow. Ichabod’s horse is found, as is his hat beside a shattered pumpkin…but Ichabod seems to have disappeared in the night.

Most adaptations of Irving’s tale point fingers at Brom Bones. While I, a seasoned mystery reader, hesitate to accept such an obvious suspect…he checks out. He is the one character who had the combination of motivation, means, and malice to carry out a plan that would terrify and potentially harm Ichabod. He knew Ichabod’s weaknesses and wanted him out of the way. Different interpretations of this story agree with me, but I was pretty impressed with the creative choices made in Tim Burton’s 1999 adaptation, titled Sleepy Hollow. In this version of the story, Ichabod is not a superstitious schoolmaster, but a skeptical scientist. This drastic change in the protagonist’s personality left even experienced readers of the source material without a proper foothold. I won’t go over the entire synopsis of this movie (but please watch it if you have not yet, it is glorious), but I will mention that Brom is taken out by the Headless Horseman near the middle of the movie. Therefore, this story in the context of Burton’s adaptation no longer has that possibility. The ending is drastically different than what is presented in Irving’s story. As a reader and someone familiar with various interpretations of this tale, I believe Brom’s place in the story is essential to that particular ending with which we are all familiar.

Here’s another unsolicited fun fact about me: When I was in grad school, I taught English composition courses as part of my program. My first semester, I taught introductory composition to a class of first-year college students. The very first week, I assigned a small piece of text to get my students practicing the rhetorical analysis and critical thinking steps we would use all semester. I chose a chunk of the opening scene of “The Legend of Sleepy Hollow,” where Ichabod first comes to Sleepy Hollow. One of the major themes we discussed as a group was the repetition of discomfort with Ichabod’s disruption of the steady rhythms of Sleepy Hollow life. From his comparatively otherworldly appearance to his passion for reading and teaching, he brings something new and exciting to the isolated village. From the very beginning, Ichabod’s presence challenges the uniformity and even the identity of Sleepy Hollow. To his frustration, Brom seems to be the only one who sees it.

So, all things considered, I have a theory for what happens to Ichabod in the original story. I do think Brom is responsible for the Headless Horseman chase at the end of the story. He had his own horse that could easily resemble the Horseman’s steed, and he was familiar with the legend (he also could have recruited one of the “Sleepy Hollow boys,” his group of local followers, to play the Horseman for him). He also claims that he had met the Horseman himself, but that could have been made up just to dig a little deeper into Ichabod’s psyche while he listened to Brom’s tale at the party. Furthermore, if the Headless Horseman was a true threat, why was Ichabod Crane the only known victim in recent memory?

However, I do not think Ichabod was killed by Brom or “spirited away” by the Headless Horseman. I believe that Ichabod left Sleepy Hollow of his own accord. All of these details come into play in that scenario: Ichabod’s superstitious nature, Brom’s willingness to scare Ichabod away from his intended, Ichabod’s insecurity about being an adequate suitor in the eyes of Katrina’s father, and the tales inspired by the history of the region. With the reasonable combination of fear and humiliation, Ichabod left the village without a word to anyone, even Katrina. In its own way, Sleepy Hollow rejected him and pushed him out. Although he was accepted and even celebrated by most of Sleepy Hollow’s inhabitants, Ichabod’s presence shattered the illusion of the region. There is something about the combination of specific occurrences in this narrative that made this event happen, if it happened at all.

Some other favorite adaptations out there are the silent film Headless Horseman (1922) and the T.V. movie The Legend of Sleepy Hollow (1999). No matter how the story is spun, it is always entertaining in its own way. One of literature’s greatest mysteries is the disappearance of Ichabod Crane. I have my own theory, but in all honesty the beauty of this story is its atmosphere of unending mystery.

Do you have any theories about what happened to Ichabod? Let me know down below, I am interested to see what more people think!

Sleepy Hollow has always been a magical place to me, somewhere quiet and spooky (just like me). The best part: Sleepy Hollow is a real place. Once the world reopens again, I am planning a trip there to experience its history and dark magic for myself. If I run into the Headless Horseman, well…I guess that means I could test my theory.

Until next time,


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