The Literature of Sleepy Hollow

(painting by William Wilgus)

 

While doing the research for my essay “Eerie Rider: The Headless Horseman’s Forays into Pop Culture” (in The Legend of Sleepy Hollow: Ultimate Annotated Edition), I encountered countless written works inspired by Washington Irving’s 1820 tale. Plenty of these qualified as glorified fan fiction and were downright painful to read, but thankfully there were also many entertaining texts. Here’s a list of eight great reads that hearken back to Sleepy Hollow:

 

1. “Sleepy Hollow” by Washington Irving

Not many readers realize nowadays that “The Legend” doesn’t constitute the only time Irving wrote about Sleepy Hollow. In this 1839 work creative nonfiction (presented as an essay by Irving’s pseudonymous narrator, Geoffrey Crayon), Sleepy Hollow is revisited in resplendent fashion. Crayon relates his connection to Diedrich Knickerbocker, fills in the backstory of how the latter learned of “The Legend,” and details the modern innovations that have now intruded upon the quaint village–doing all in a comedic tone that makes the essay a fine companion piece to the original story.

 

2. Ghost Story by Peter Straub

Tellingly, the first ghost story interpolated in Straub’s 1979 novel (which revolves around the frightful fireside tales passed among the haunted members of the Chowder Society) is a variation on “The Legend of Sleepy Hollow” (ultimately mashed up with The Turn of the Screw). The narrator recounts his experience decades earlier as a teacher in a one-room schoolhouse in a rural New York village, and his encounter with the malevolent revenant of a man that perished from a grievous head injury. How thematically appropriate that Straub’s complex narrative of spook tales come to terrifying life draws upon Irving’s tale of a schoolmaster harassed by a seemingly all-too-real local legend.

 

3. Sleepy Hollow by Peter Lerangis

This 1999 novelization is a must-have for fans who just can’t get enough of the Tim Burton film adaptation. Lerangis follows the cinematic narrative faithfully, capturing Burton’s Hammer-Horror-style revision of Irving in vivid prose. A special treat is the scene at novel’s end involving the retreat of the no-longer-Headless Horseman with Lady Van Tassel into the Tree of the Dead–a scene presented here from the Horseman’s very own point of view.

 

4. Sleepy Hollow High by Christopher Golden and Ford Lytle Gilmore

This quartet of linked novels (Horseman [2005], Drowned [2005], Mischief, [2006], Enemies [2006]) is marketed as young adult fiction, but can be enjoyed by readers of all ages. Sleepy Hollow is besieged by a series of terrifying monsters, all linked in some fashion to the legendary Headless Horseman. The Horseman himself proves plenty frightening, but his character arc over the course of the four novels allows him to range beyond mere decapitating menace.

 

5. Rise Headless and RideBridge of Bones, and General of the Dead by Richard Gleaves

The first three volumes (2013/2014/2015) of the Jason Crane series (which also includes 2018’s Salem: Blood to Drink) are set square in a modern-day Sleepy Hollow that is haunted by its early history. These novels draw lovingly on the original “Legend” and transform its materials into an epic narrative centered on the Headless Horseman (whose mythos is thoroughly developed, and whose imagining here is unrivaled for inventiveness). Featuring a diverse cast enmeshed in supernatural intrigue, Gleaves’s books read like True Blood by way of Washington Irving, and are positively begging to be developed into a Netflix series (shot on location in Sleepy Hollow!).

 

6. Grimm Fairy Tales Presents: Sleepy Hollow by Dan Wickline

This modern retelling actually reimagines the Headless Horseman as an avenging hero–which isn’t to say that the figure (who looks from the neck stump down like Gene Simmons on steroids) has been stripped of menacing aura. Grue is splashed across the page in this graphically violent graphic novel, in which the Horseman stalks his prey with all the relentlessness and killer creativity of a classic cinematic slasher.

 

7. The Devil’s Patch by Austin Dragon

Irving’s story is reworked as a weird western in this 2015 novel (a sequel to Hollow Blood), in which a gunslinging posse travels far north of Sleepy Hollow in an attempt to kill the infernal Horseman in his new lair. I include this one on the list for its thrilling climax, blood-soaked and action-packed, and featuring one incredibly surreal image of the Horseman that will not be soon forgotten by the reader.

 

8. The Spellbook of Katrina Van Tassel by Alyssa Palombo

Ichabod in a bodice-ripper? Sounds like a recipe for disaster, but Palombo pulls it off in this atmospheric and historically-accurate gothic romance. The novel also works as a “feminist retelling” (as Palombo terms it in her author’s note) of Irving’s story, as Katrina is situated here as narrator, central character, and ultimate recorder of the Horseman’s legend. Various female writers have offered their take on “The Legend of Sleepy Hollow” in recent years, but this spellbinding book is head and shoulders above the rest.

 

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