“The Legend of Sleepy Hollow” is a short story, originally published in The Sketch Book of Geoffrey Crayon, Gent. “Geoffrey Crayon” being a pseudonym of Washington Iriving.

It tells the story of Ichabod Crane, a schoolteacher in a region of New York known as Tarrytown in the early 19th-century. He is—if I may cut through the florid 19^th-century lingo—kind of a jerk. He’s mean to his students, unless he sees an opportunity of mooching free meals off their mothers or flirting with their older sisters. 

Eventually, Ichabod’s fancy is caught by Katrina Van Tassel, the daughter of the wealthy Baltus Van Tassel. One thing  that’s interesting is that Ichabod seems to be interested in her largely for a wealth—whether he has affection or even mere lust for her seems beside the point.

But another of Katrina’s suitors, the large, vigorous, Brom Bones (actually Brom Van Brunt, but his nickname is Brom Bones) does not take kindly to the girl he’d been wooing spending all her time with the awkward schoolmaster. 

These are the three main characters, and they’re all kind of humorously unlikable. Ichabod is a selfish moocher, Katrina is a vapid tease, and Brom is what we would today call a jock frat boy. The main body of the story is more like a sit-com than a ghost story.

The ghost aspect comes from the setting—Tarrytown, a sleepy, dreamy village in the Hudson valley where, Irving tells us:

“…population, manners, and customs remain fixed, while the great torrent of migration and improvement, which is making such incessant changes in other parts of this restless country, sweeps by them unobserved. They are like those little nooks of still water which border a rapid stream where we may see the straw and bubble riding quietly at anchor or slowly revolving in their mimic harbor, undisturbed by the rush of the passing current.”

In other words, it’s a place that seems removed from modernity—modernity, in this case, being 1820. Even when Irving wrote the story, “Sleepy Hollow” was hearkening back to an earlier era. No doubt he was targeting those 1790s kids who felt nostalgic for their childhood.

Anyway, things culminate with Ichabod going to a large harvest party at the sprawling Van Tassel farm, where folks swap ghost stories, such as the one about “The woman in white that haunted the dark glen at Raven Rock, and was often heard to shriek on winter nights before a storm, having perished there in the snow.” And finally, of course, the region’s most popular legend: the story of a ghostly Hessian soldier who, having lost his head to a cannonball in the war, rides forth each night in search of a replacement. 

Ichabod, who is a devoted reader of Cotton Mather, is much troubled by such tales. He leaves the party in a state of agitation, and our narrator suggests that perhaps Katrina has dumped him, although this is ambiguous. At any rate, Ichabod is riding home alone, feeling rather miserable when he encounters a huge, headless rider mounted upon a black horse.

Furiously, Ichabod urges his own horse towards the old church bridge, which, according to a story of the horseman related by Brom Bones, the horseman will not cross. Ichabod successfully manages to cross the bridge and turns just in time to see the horseman hurling his head at him. 

Yes, that’s right—his head. The horseman carries his severed head with him on his saddle. And this is where the story becomes a bit ambiguous because the next day, as the townsfolk investigate Ichabod’s sudden disappearance, they do not find a head at the old church bridge, but do find the shattered remains of a pumpkin. 

The story is deliberately vague after that—while Ichabod is never seen again in Tarrytown, some say he simply moved, and is alive and well in another part of the country. Brom Bones—who, we are told, marries Katrina, looks “exceedingly knowing” whenever anyone brings up the subject of Ichabod, suggesting that perhaps the notorious prankster had simply disguised himself as a headless horsemen, seeking to frighten off his rival.

Of course, the more superstitious residents of the town believe that Crane became a victim of the ghostly Hessian. And after all, since we already have strong reason to think Ichabod was spurned by Katrina at the party, why would Brom have even needed to pull such an elaborate stunt? (Unless he was just adding injury to insult, which would be exactly the kind of move we might expect from Brom.)

This brings me back to what I think is the most curious thing about this story: it plays out like a romantic comedy—or more accurately, one of those anti-romantic comedies where all the characters seem self-absorbed, and the comedy results from the interplay of their attempts to get what they want. In fact, if you take away all the supernatural elements and think of it in modern terms, it’s basically a mean-spirited high-school comedy, where the rich cheerleader and the superstar quarterback screw over the know-it-all nerd.

Which seems like the sort of thing that might actually happen, and indeed almost makes me wonder if the eponymous “Legend of Sleepy Hollow” isn’t the thing about the headless ghost at all, but rather the legend of a love triangle that ended in a bizarre prank. In other words, it seems almost like the sort of thing that could have actually happened. Apparently, Irving did know people named “Ichabod Crane” and “Katrina Van Tassel.” Real-life Ichabod Crane was a captain in the army, not a schoolteacher, but real-life Katrina seems to have been more or less like the character in the story, which again makes me wonder how much of this was based on real events or gossip Irving picked up. 

But obviously, it’s the ghost aspect that has made this story famous. And is it ever famous! It’s one of the first and most iconic pieces of post-revolution American literature, and has been adapted many, many times. (More about that later this month.) There are places all over the country named “Sleepy Hollow.” Ichabod and the ghostly Hessian are commemorated on postage stamps and in statuary. Most people know the story even though they never read the original. It’s the quintessential American ghost story.