Retold Stories: Sleepy Hollow

Updated: Oct 3

The Headless Horseman, thundering across a covered bridge on Halloween night, chasing the hapless Ichabod Crane. What could be more evocative of the spooky reads we love when autumn chill returns? This story has been giving good fright since 1820 when Washington Irving created his short story masterpiece, "The Legend of Sleepy Hollow". The tale has inspired movies (I love the Tim Burton version) and a television show. And it has also inspired other authors to take on the tale. "The Spellbook of Katrina Van Tassel" by Alyssa Palombo, "Sleepy Hollow: Rise Headless and Ride" by Jason Crane, and "The Hollow" by Jessica Verday, to name a few.

What is it about this story that draws authors to make their own version? I can't speak for anyone else, but for me, the story speaks to the dread of being an outsider - someone new to a tight-knit community who doesn't fit in. It also speaks to the need to escape - in one sense, quite literally, to escape the Horseman, but also I think Ichabod Crane is escaping his old life when he comes to Sleepy Hollow and I'm always curious what he is running from and where he is running to.


For my retelling, which will be coming out in time for Halloween, my protagonist is Isabelle Crane, a young woman looking to escape a stifling life where she is grudgingly tolerated. She jumps at the chance to escape her situation as a schoolmistress in Sleepy Hollow - a post she isn't really qualified for, but nevertheless she takes off into the unknown. Isabelle is going to discover there are secrets she doesn't know and dangers hiding behind the smiling faces of Sleepy Hollow village.


While Washington Irving set his tale in 1790; mine is set in 1890 and that is the beauty of this tale; you can change the time period and come up with a whole new set of challenges for Ichabod. The original story is also ambiguous as to what really happens to Ichabod. Did the Horseman get him? Did Ichabod escape? Did Brom Bones, his rival for Katrina, scare him off? Irving leaves it up in the air for the reader. Not all retellings are as unclear as Irving left it and for myself, I prefer a more clear-cut ending. I also like versions where the monster might just be the humans.


Whether it is the original short story, a modern retelling, a movie version or the animated cartoon featuring Bing Crosby's voice, the characters of Irving's tale endure and inspire. Make yourself a hot cocoa or pumpkin spice latte and curl up with a version when you want a dose of chills and Halloween ambience.



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