When the first breath of autumn touches the air, thoughts turn to colorful leaves, cinnamon-scented goodies, and pumpkins. Halloween can’t be far away. And each Halloween the headless horseman of Sleepy Hollow rides. Most of us don’t stop to think how closely related Halloween and “The Legend of Sleepy Hollow” actually are. They grew up together.
Many of us in the Boomer generation likely learned about Washington Irving’s classic through Disney’s The Adventures of Ichabod and Mr. Toad, or perhaps through the shortened version shown on television, The Legend of Sleepy Hollow. We grew up with that scary song, “Headless Horseman” ringing in our ears around Halloween. We may have even noticed the “Legend of Sleepy Hollow” commemorative postage stamp issued in October 1974, straight out of Tarrytown. However we learned about it, Sleepy Hollow had become part of our collective memory and an integral part of Halloween.
Think about how strange this is.
Not many folks can probably name anything Washington Irving wrote, apart from “The Legend of Sleepy Hollow” and “Rip Van Winkle.” They probably can’t tell you the title of the book in which both of these stories first appeared. (That will be revealed a little further on.) It isn’t widely known today that Irving was the first American to make a living primarily by writing and that he interacted with eight presidents from George Washington through Zachary Taylor. He wrote a five-volume biography of Washington. Today he’s mainly remembered for Sleepy Hollow. He never mentioned Halloween in his books.
This is an odd state of affairs. Not only did Washington Irving write a bestselling satirical history of New York City, he also served on the staff of the American Minister to England and, later, became the United States’ Minister to Spain. He lived a remarkable life for a writer. And he put Sleepy Hollow on the map. And Halloween. He did the latter without ever using the word.
Sent to Tarrytown as a tween during a yellow fever epidemic, Irving encountered Sleepy Hollow, and, if he’s to be believed, heard the story of the legend from an African-American mill worker. I say “if he’s to be believed” because as he was getting on in years, Irving kept the mystique of the tale alive, maintaining the fiction of having found it in the papers of Diedrich Knickerbocker. Diedrich Knickerbocker was one of Irving’s noms de plume.
The story itself is a humorous one. We tell it to children probably in much scarier tones than it was written. Ichabod Crane is cartoonish both in description and action. He’s not exactly the hero of the tale. A self-serving itinerate teacher, he sets his sights on Katrina Van Tassel because she can provide a means of early retirement, with her father’s great wealth. Her rustic lover, Brom Bones, takes none too kindly toward the pedagogue and when Crane is chased out of Sleepy Hollow by a headless horseman, many assume it was Brom behind the ghost. The story was published in a book titled The Sketch-Book of Geoffrey Crayon, Gent. in 1820. Geoffrey Crayon was another pen name Irving favored.
Halloween was largely unknown in the United States at the time. The spooky autumnal holiday only made inroads after large-scale Irish and Scottish immigration established Celtic communities in America. Although some Irish had emigrated and landed in the United States earlier, the Great Famine beginning in 1845 brought great numbers. Halloween appeared in small, local pockets and young people found pumpkins ready-made for jack-o-lanterns. Back in the British Isles, where pumpkins don’t grow naturally, turnips had traditionally be used. By the 1850s, however, pumpkins already had a scary autumnal story in Irving’s legend.
Fast forward about two centuries from when Irving’s story was published in 1820. Fox television surprised even itself with the early success of the four-season series Sleepy Hollow. A dashing Ichabod Crane, somehow morphed with Rip Van Winkle, awakes in twenty-first century Sleepy Hollow to prevent the four horsemen of the apocalypse from destroying the world. It seems that the show’s ensemble of writers and directors failed to grasp that the African-American police lieutenant, Abbie Mills, was crucial to the outlandish plot they’d concocted. As her role diminished, interest began to fade. Nevertheless, the series spun off novels and even graphic novel tie-ins. Fan wikis were established. The charming story of an itinerant school teacher from Connecticut became part of a supernatural horror show of weekly monsters chasing a former Oxford professor turned American patriot and modern-day expert witness.
The two centuries between these two renditions of the story had been filled with many other cultural expressions of Irving’s tale, even as Halloween was catching on. Arguably, this began with the invention of celluloid. Early American filmmakers, hungry for content, latched onto Irving as early as 1903. The first feature-length film of Sleepy Hollow, starring Will Rogers as Ichabod Crane, was released in 1922 as The Headless Horseman. Before the mid-century mark Walt Disney had released its iconic cartoon of the legend. From that point on, television adopted Crane, Katrina, and Brom. And, of course, the headless horseman. Television movies appeared and networks showed episodes of established series with a Sleepy Hollow theme, generally near Halloween.
Around 1993 a make-up effects director, Kevin Yagher, began working with screenwriter Andrew Kevin Walker on a project that Paramount Studios would eventually assign to Tim Burton to direct. Sleepy Hollow was one of three feature-length movies based on Irving’s tale released in the autumn of 1999. It was, however, the most influential of them. The half-century nap between Disney and Burton ended with wide-eyed enthusiasm for Irving’s short story. The influence of Burton’s film on the Fox series is obvious at a glance. This was now a horror story to dust off every October. Three years ago Paramount announced that Lindsey Beer would be writing and directing a new Sleepy Hollow feature film. The release date hasn’t yet been announced.
Burton’s film, following Disney, firmly settled Ichabod Crane’s visit to Sleepy Hollow on Halloween. Disney had introduced a headless horseman holding not a pumpkin, but a flaming jack-o-lantern. Burton’s film opens with a scarecrow with a jack-o-lantern head. Both the Disney film The Adventures of Ichabod and Mr. Toad, and the television version of The Legend of Sleepy Hollow six years later, were released in October. By the mid-twentieth century Halloween had become mainstream. And Ichabod Crane was right there with it.
Behind the scenes, over the past century and a quarter, America has been developing a fascination with Halloween. During Irving’s lifetime Halloween had not yet captured the American imagination. It’s doubtful he even knew of it. “The Legend” itself makes no mention of the holiday or even of jack-o-lanterns. Halloween took many decades to become mainstream. Again, Boomers may have been the first generation that grew up with great expectations for the autumnal holiday, even if it’s not a day off work. When Halloween really took hold it would almost rival Christmas as a spending holiday. The headless horseman’s pumpkin early on suggested itself as a companion to the growing American interest in what we now think of as the scary season. It has even been suggested that the reason Americans think of autumn as the spooky time of year, rather than the traditional English Christmas, is because of Irving’s story.
Although born of different parents, “The Legend of Sleepy Hollow” and Halloween grew up together, creating the now standard and expected idea that fall is scary. October is for watching horror movies. And for horror tourism. The Great Jack-o-Lantern Blaze, sponsored by Historic Hudson Valley, draws enthusiastic visitors to Sleepy Hollow annually from far and wide.
“The Legend of Sleepy Hollow” is Americana in the widest sense. Embracing ideas from elsewhere—Irving was living in Europe when he wrote his story—and adapting to fit the needs of a group of rag-tag revolutionaries growing into a new world empire, its humble pumpkin crashed into Halloween. The two have been inseparable ever since.
Steve A. Wiggins (https://steveawiggins.com) is the author of Sleepy Hollow as American Myth, recently released by McFarland; The Wicker Man (Auteur, 2023); Nightmares with the Bible (Lexington, 2020); and Holy Horror (McFarland, 2018). He also writes horror fiction under a pseudonym. A former professor, he now makes a living as an editor for an academic press in New York City.