Ichabod Crane and the Headless Horseman: The Legend of Sleepy Hollow Adaptations

If you’ve been reading my blog posts long enough, you’ll know that I enjoy a good scary story, a good folktale, and a good classic. So, I guess it’s a good question as to why it has taken me so long to finally get around to reading The Legend of Sleepy Hollow, which is a classic scary story about a chilling folktale. Regardless of the “why”, I finally did, and I just had to share some of the creepiest, most interesting adaptations with you. As with all these lists, I suggest starting with the original first, but you can take the rest of these in whatever order you wish. Try one, try two, try all of them…the choice is yours. I hope you find something to chill you to the bone!

Let’s start this list off with the spooky story that started it all! The Legend of Sleepy Hollow is the story of Ichabod Crane, who moves to the sleepy New England village of Tarry Town to be the new schoolmaster. Crane is well-liked and eager to please, and being a bachelor, soon sets his eyes on the beautiful Katrina Von Tassel. But, this draws the unwelcome enmity of Brom Bones, one of the other eligible bachelors in Tarry Town, who also has plans for marriage involving Miss Von Tassel. Now, the citizens of Tarry Town are deeply superstitious (as is Ichabod Crane). And one of the biggest legends that circulates around the area is that of the Headless Horseman, a Hessian soldier who was decapitated…with a cannonball. They say that he roams about at night, searching for a new head to replace the flaming pumpkin he wears atop his shoulders. It’s really a short story, so I won’t say too much more about it. But, I can tell you that this collection that I’ve highlighted here also includes three other stories: “Rip Van Winkle,” “The Specter Bridegroom,” and “The Devil and Tom Walker.”

As a child, I loved spooky stories (although nothing too scary) and The Adventures of Ichabod and Mr. Toad was one of those tales that was just the right amount of fright without making me sleep with the lights on. One of Disney’s lesser-known classics, this little feature consists of two stories: The Legend of Sleepy Hollow and an abridged version of The Wind in the Willows. There’s not a lot to add to this description, except that the narration and singing is performed by Bing Crosby (which I hadn’t realized when I watched this as a child, but upon seeing it as an adult, turned out to be a real treat!) Speaking of Bing Crosby, if you’re not tapping your toes and humming along to the song Brom Bones sings about the Headless Horseman, then I don’t even know what to say! This is a really fun introduction to the classic tale of terror for younger viewers. And adults will definitely find something to enjoy here, too.

Gris Grimley is an incredibly talented artist, so you can imagine, I’m sure, how excited I was to see that he had done a graphic novel adaptation of The Legend of Sleepy Hollow. This chiller is a somewhat abridged retelling of an already short book, but readers who prefer their stories to be heavily illustrated (as I do!) will love this! And if you enjoyed this book, consider checking out my first introduction to Grimley’s work– Frankenstein, or The Modern Prometheus, as well. A quick note: unlike traditional graphic novels, which are made up of panels and drawings, Grimley’s books are more text-heavy, meaning that you’ll get to read a lot more of the original story than you would in most graphic novels. Not sure what I’m talking about? Pick up the book and check it out for yourself. You won’t be disappointed!

Horseman: A Tale of Sleepy Hollow is a sequel of sorts to the original tale of Ichabod and Katrina and Brom. Everyone in Sleepy Hollow has heard about the Horseman, but no one really believes in the old legends. Not even Ben Van Brunt’s grandfather, Brom Bones–the same Brom Bones from the original tale–and he was supposedly there when the horseman chased Ichabod Crane out of town. But, Brom claims that it’s all just a legend, designed to scare gullible people and give the gossips something to talk about. It’s been thirty years since that day, and 14-year-old Ben loves to play “Sleepy Hollow boys,” reenacting the events of that fateful night. (To be fair, what kid doesn’t enjoy playing ghoulish games once in a while?). But, the games are interrupted one day when the group discovers the headless body of a child in the woods near the village, and young Ben is forced to confront everything that the adults have ever told him. Because either the Headless Horseman is real (and he rides again) or there is something else in these woods–something far more sinister than anything Ben could have imagined.

If you were looking for a version of The Legend of Sleepy Hollow that’s not set in Colonial America, then this just might be what you’re looking for. Sleepy Hollow is a horror film starring Johnny Depp and Christina Ricci. Here, Depp plays Ichabod Crane, a New York Detective who is unpopular with the rest of the force. He’s sent off on an assignment to the small town of Sleepy Hollow in order to investigate a series of murders where the victims have all been beheaded. Of course, the townsfolk seem to think that this is somehow tied up in the local legend of the Headless Horseman, a story about a Hessian soldier who was decapitated. But, Crane thinks that there must be a logical answer, and sets about using his wiles and his special gadgets to figure out the truth. He soon meets and falls in love with the beautiful Katrina Von Tassel, sweetheart to the burly Brom Bones, and decides that he’ll solve the murders and prove himself to her.

Katrina is an important figure in the Sleepy Hollow mythos, but she’s never truly been given a voice…until now. When the new schoolmaster, Ichabod Crane, arrives in the little village of Sleepy Hollow, Katrina Van Tassel is immediately drawn to him. The two bond over books and music, and soon their friendship blossoms into something more. But, Crane had very little money and no social standing–and therefore had nothing of value that he can offer a beautiful, wealthy woman like Katrina. None of that matters to her, but her father is determined to see her married to Brom Van Brunt, her childhood friend-turned-enemy, who is also from a wealthy family and could provide for her properly. So, the lovers take to sneaking away at night for secret rendesvous in the woods, praying all the while that they never encounter the local legend of the Headless Horseman. But, when Crane suddenly disappears on All Hallow’s Eve, Katrina is left alone and in a perilous position. So, she enlists the help of Charlotte Jansen, who is rumored to be a witch, and the two turn to magical means to determine what really happened to Crane that night. But, the things they uncover will force them to question everything. The Spellbook of Katrina Von Tassel is a gripping, suspenseful, and romantic tale where nothing is as it seems.

Erin

I'm the Reader's Advisory Librarian at WPPL. My interests include old horror films, classic novels, manga and anime, paper-crafting, and plants. If you like my suggestions, you can request personalized recommendations from me on My Librarian page.