10 Essential Sleepy Hollow Retellings
Posted on October 9, 2025
by Sam P
Published in 1820, The Legend of Sleepy Hollow from Washington Irving’s short story collection The Sketch Book of Geoffrey Crayon, Gent., remains one of America’s most famous short stories. It’s also one of the more popular iterations of a folkloric figure — The Headless Horseman.
Various cultures, primarily in Europe, share evidence of some version of a rider who is either headless or carries some sort of missing head while seeking revenge on his be-header. Over time, modernized mounts such as the headless motorbike rider of Japan have also been adopted into the modern-day urban legend canon.
This list features some of the most popular adaptations in our collection, such as Tim Burton’s 1999 film Sleepy Hollow, as well as a few tales that were inspired by the legend itself like Kelley Armstrong’s modern take, The Haunting of Payne’s Hollow.
the haunting of paynes hollow by Kelley Armstrong
When Sam Payne's grandfather dies, she's summoned to the will reading at the family's lakefront property of Payne's Hollow. She didn't expect to be bequeathed the property-- much less with strings attached. Read on to see if she survives staying for a month at the cottage where secrets come unearthed.
sleepy hollow
With his signature style, Tim Burton's loosely adapted version of events features constable Ichabod Crane to investigate an upstate hamlet whose townspeople have been terrorized with a series of beheadings.
the spellbook of katrina van tassel by Alyssa Palombo
Expanding upon Ichabod Crane's vanishing near the end of the original story, Katrina Van Tassel enlists the help of her friend (and witch) Charlotte Jansen to investigate the truth surrounding his suspicious disappearance.
raising the horseman by Serena Valentino
In preparing for the 200th anniversary of the Headless Horseman's most infamous pursuit, Kat Van Tassel receives the original Katrina Van Tassel's diary. While resistant to familial expectations, this journal, as well as the arrival of Isadora, are just the beginning of Kat questioning everything she knows. Though a teen novel, it's a fun, Halloween-tinged story.
hollowed by Jessica S. Taylor
This re-imagining posits the villain as the Irish Dullahan. Though the Headless Horseman protects the supernatural town of Sleepy Hollow, it is at the cost of one sacrifice a year. When Katrina Van Tassel is chosen as the next victim, her attempt at escape reveals dangerous mysteries that have stayed buried for far too long.
horseman by Christina Henry
Ben Van Brunt is a proud descendant of the larger-than-life Brom Van Brunt. In this retelling, young Ben stumbles upon the dismembered corpse of another boy in the haunted forest surrounding Sleepy Hollow. What follows is Ben's independent investigation into what lurks in the shadows, has been hunting the townsfolk their livestock, and some of the secrets surrounding Ben's lineage.
splinter by Jasper Hyde
Dr. Drusilla Van Tassel is Sleepy Hollow's youngest Medical Examiner. When her sister Katrina's friends start showing up in the morgue headless, she has her work cut out for her. On top of Dr. Van Tassel's ex, Ichabod, coming back into town, she has to contend with monster hunting when faced with the Headless Horseman himself.
hollow by Shannon Watters
In preparing for the 200th anniversary of the Headless Horseman's most infamous pursuit, Kat Van Tassel receives the original Katrina Van Tassel's diary. While resistant to familial expectations, this journal, as well as the arrival of Isadora, are just the beginning of Kat questioning everything she knows. Though a teen novel, it's a fun, Halloween-tinged story.
jack of fables deluxe book 1 by Bill Willingham
A spin-off of Bill Willingham's Fables series, Jack of Fables collects Jack's (of Nimble, the Beanstalk, etc. fame) adventures while exiled from Fabletown. Though reading part of the original series will enhance reader's experience, it is not necessary. Issue 16 is a special in which Jack adopts another moniker; Jack O' Lantern.
headless by Alexander Banchitta
Salem, Massachusetts in 1987 is not the first setting most people think of when the Headless Horseman is brought up. When two brothers roll up to town, not only do they reckon with the rider, they also run into your average bullies, witches, and even the Knight's Templar.
Consider reading the original story before or after checking out one of these titles! See what you remember from the original (if anything at all), or if your memory has been influenced by the various versions told over the years.
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