From the listless repose of the place, and the peculiar character of its inhabitants, who are descendants from the original Dutch settlers, this sequestered glen has long been known by the name of Sleepy Hollow…

Halloween is my favorite holiday, probably due to the many fond memories of my mom putting up decorations and trick-or-treating (aside from my dad scaring me with his Crypt Keeper mask). The holiday evoked my imagination and stirred my excitement as I got to choose what I wanted to dress-up as that year. I feel what really makes Halloween special is it gives us a chance to feel like we can enter into this whole different world, to pretend to be who we really want to be, for a single night. So, whenever the holiday draws close, I get really pumped to re-watch my favorite Halloween flicks and read spooky literary stories. One of those stories is Washington Irving’s account of a ghostly phantom haunting a small settlement of Dutch colonists.

The Legend of Sleepy Hollow is both a charmingly quaint story of an awkward schoolteacher’s attempts at wooing a rich landowner’s daughter, and the characterization of gothic horror seen in such tales as The Castle of Otranto, The Beetle or Dracula.

The tale begins by descriptively narrating the history of the nearby New York Tarry Town, as well as its surrounding countryside. One is nicely spell bounded into the 18th century landscape with the introduction of Sleepy Hollow, complete with spooky origin stories that excites the emotional aesthetic of the reader:

A drowsy, dreamy influence seems to hang over the land, and to pervade the very atmosphere. Some say that the place was bewitched by a High German doctor, during the early days of the settlement; others, that an old Indian chief, the prophet or wizard of his tribe, held his powwows there before the country was discovered by Master Hendrick Hudson. Certain it is, the place still continues under the sway of some witching power, that holds a spell over the minds of the good people, causing them to walk in a continual reverie.

Ichabod Crane is a colorful but bumbling character who seems due to fail in his pursuits of Katrina Van Tassel. In fact, he probably should have concentrated his efforts on teaching the local school children, for while he was stern in his teachings, it seemed the community really valued him for his services. It is only when he decides to pursue Katrina, not only for her beauty, but mainly for the beautiful house and acres of land that come as a package-deal, does he exit his comfort zone and dooms himself to ridicule.

For Ichabod is not a great catch for the Dutch farmer’s daughter. Ichabod’s physique can be summed-up as a “scarecrow eloped from a cornfield.” And compared to his rival Brom Van Brunt, who is a skilled horseman and is of a muscular physique, poor Ichabod doesn’t stand a chance to win Katrina’s hand.

Irving does a wonderful job of smoothly treading the binary of the appealing society of the small New York towns and the horror of the unknown in the surrounding rural area. His masterful use of language heightens the foreboding feelings that steadily increase throughout the story, from when Ichabod first hears the ghost story of the headless horseman, to his fateful ride home.

A quick note to his use of language, any linguaphile out there might be excited to spy some words that date as far back to the 14th century. For example, wight, meaning “person” appears in Irving’s tale, as well as in Chaucer’s The Canterbury Tales, written in middle English.

The Legend of Sleepy Hollow is a tale I have re-visited again and again for the past couple of years. As October rolls around, I dust-off my copy of Irving’s spooky tale and transport myself back into 18th century, to the year 1790, to relish the emotional aesthetic of the sublime: terror. This terror is best illustrated with a steady build-up of the sublime as Ichabod rides through the haunting countryside and is released upon the reader when he is trying to flee from the headless horseman (if you’re interested in reading more on the gothic aesthetic, I highly recommend a novel I read for my college-level gothic literature class: Edmund Burke’s A Philosophical Enquiry into the Origin of Our Ideas of the Sublime and Beautiful).  

Of course, the best part of the legend is with the arrival of the headless horseman. When the ghostly rider comes upon the scene, he is bound to send a shiver down any reader’s spine. An interesting fact is Irving wrote the legend while touring Europe, no doubt listening to a variety of the headless horseman legend (if you want to read more on the lore of the headless horseman, see my 2018 Halloween article, “The Many Faces of the Headless Horseman”.

To sum-up a widely held belief, the appearance of the headless horseman is usually visited upon those who are scheming deviants, meddling in affairs they should not meddle in. Also, Ichabod’s name is thought to have been stolen from an army captain in Sackets Harbor called Ichabod Bennet Crane, and the character’s mannerism catered after Jesse Merwin, a local schoolmaster at Kinderhook. Supposedly, the namesake of the foolish schoolmaster wasn’t too pleased to have his name bestowed on such a ridiculous character.

Overall, what really draws me to Washington Irving’s legend of the headless horseman is the mysterious fate of Ichabod and the romantic landscapes Irving exemplifies in his writing. If you want a creepy ghost story to psych you up for Halloween, Irving’s legend of a headless horsemen fits the bill perfectly.

Title image by Denys Tsiperko.

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By S. H. Paulus

Summer graduated from the University of Central Florida with a bachelor’s degree in English Literature and a minor in Technical Communications. She first fell in-love with fantasy after her father read her The Hobbit growing-up. Her love for writing began when she wrote a collection of short stories in elementary school titled Reading Stories, and has been writing ever since. Aside from writing, she spends her free time reading, playing video games, and enjoys long walks on the beach. As well, she enjoys reading theoretical papers on Postcolonialism and enjoys a good, Postmodern novel when she needs a breather from her obsession with fantasy. Her favorite fantasy authors are Elizabeth Haydon, Brian Lee Durfee, Steven Erikson, Mark Lawrence, Brandon Sanderson and Tolkien. Aside from fantasy, she adores works by the Brontë sisters, David Foster Wallace and Tolstoy, her all-time favorite novel being War and Peace. She resides on the Space Coast with her fiancé and two cats, all while working on getting her first novel published. You can follow her on Twitter @SHPaulus1.

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