Our tale begins with Ichabod Crane, a newcomer to Sleepy Hollow who arrived in search of a teaching job. He soon learns of the town legend of the Headless Horseman. This unfortunate soul is a ghost whose pumpkin head serves as a frightening (and rather odd) substitution for a human head. Eventually, Mr. Crane crosses paths (literally) with the spooky sportsman – and the results of said encounter are not pleasant. 

It’s a tale told on Mischief Night while carving jack-o-lanterns in anticipation of Halloween. Or perhaps you heard it while gazing into the heart of a campfire on a chilly night with your friends. Or maybe you heard it at one of those slumber parties in high school where everyone vows to stay up all night, yet they’re all sound asleep by midnight and you’re left alone, wondering when you’ll hear the hooves of the horse galloping down the street. But don’t worry, you won’t… Or will you? After all, like many tales, the story of the Headless Horseman isn’t solely rooted in fiction.

In 1820, Washington Irving’s The Legend of Sleepy Hollow was published. Sleepy Hollow is a real town, located in New York State. According to Lesley Kennedy from History.com, Irving was not the first to tell the tale of the unlucky horseman. The legend goes as far back as the Middle Ages, with various stories passing through the public sphere. According to historian Elizabeth Bradley, it’s probable that Irving’s horseman is inspired by The Chase, a translation of The Wild Huntsman by Gottfried Bürger. The Chase was written in 1796 by Sir Walter Scott, and The Wild Huntsman is believed to have roots in Norse mythology . As noted by the New York Historical Society, others believe Irving’s story is based off of a real-life Hessian soldier who lost his head when he was hit by a cannonball during the Battle of White Plains in 1776. Interestingly, this battle took place during the Halloween season .

With Halloween time upon us, now seems like the perfect time to indulge in this timeless tale of the man with a jack-o-lantern head. Thankfully, various film adaptations exist, including “The Legend of Sleepy Hollow” and “Sleepy Hollow,” both released in 1999. There are many other films based off of this legend as well. Heck, there’s even a Smurfs movie titled “The Legend of Smurfy Hollow.” Whichever film you choose, just remember that it’s only a movie… or is it?