Growing up, one of my favourite Halloween movies was Disney’s The Adventures of Ichabod And Mr. Toad (1948). I don’t really remember what Mr. Toad was about, but I do remember being terrified of the Headless Horseman. Although, my fear of a ghost with a jack-o-lantern for a head didn’t stop me from watching the cartoon multiple times a year. For anyone who hasn’t seen this cinematic adventure, you can watch the full version on YouTube.

I’ve never watched any modern adaptations of Washington Irving’s short story, so my only encounter with the Headless Horseman was through Disney. That is, until this year, when I decided to finally sit down and read this ghostly tale.

“The Legend of Sleepy Hollow” was first published in 1820 as part of Irving’s collection, The Sketch Book of Geoffrey Crayon, Gent. When The Sketch Book was first released, it was published under Irving’s pseudonym, Geoffrey Crayon, which he used throughout most of his literary career. Irving wrote much of this collection when he was travelling throughout England. During his time abroad he dabbled in other forms of literature and storytelling, including German folklore, which undoubtably contributed to the creation of his later stories, including “The Legend of Sleepy Hollow.”

The small town of Sleepy Hollow is immediately set as a superstitious locale. The townspeople often share stories of ghosts, demons and witchcraft, and many genuinely believe that they witness spectral events at night.

Ichabod Crane, schoolmaster of Sleepy Hollow, spends his spare time reading The History of New England Witchcraft, by Cotton Mather, who was a key figure in the Salem Witch Trials. Irving was writing just over 100 years after the Salem Witch Trials, so it’s not surprising that his small, albeit fictional, Puritan town is still reeling over the possibility of witches and demons. Ichabod, who is described as being highly superstitious, sings psalms to himself at night while walking home in the hopes of warding off whatever evilness might be attempting to ail him.

But what happens to poor Ichabod? As many know, he encounters the Headless Horseman on his way home from a party, where he was trying to woo the town sweetheart, Katrina Van Tassel. While at this function, Brom Bones, a well-known prankster from town, shares stories about Sleepy Hollow’s most popular ghost: the Headless Horseman. Many believe that this ghost is a soldier from the American Revolution who is looking for his lost head.

The tales woven by Brom Bones are so intricate and detailed that they undoubtably frighten Ichabod. He begins to worry about whether or not this frightful spectral is in fact real, and if he will encounter it on his way home later that evening. 

Of course he will.

But the ending of the story doesn’t simply tell of Ichabod’s ghostly disappearance. Or does it? The reader is left with two endings to ponder: does the Headless Horseman whisk Ichabod away, or was Ichabod able to escape and start a new life elsewhere? The only evidence left is his hat and a smashed pumpkin.

In roughly 25 pages, Irving takes you on an eerie adventure, complete with ghosts and demons. His descriptions are so vivid that you’re able to place yourself in Sleepy Hollow amongst the characters, and easily envision their fears. With such detailed descriptions, the reader is able to decide for themselves if the Headless Horseman is in fact real, or a legend. The answer, of course, depends on how convinced you are of Irving’s writing.

You should read this short story if you’re looking for a spooky read that will take under an hour to get through.