Memorably filmed by Tim Burton in a 1999 adaptation that changed a number of details of Irving’s original story, ‘The Legend of Sleepy Hollow’ is, along with ‘Rip Van Winkle’ (which we have analysed here), Irving’s best-known work. First published in 1820, the story is variously regarded as a Gothic tale and a modern folk story about the early history of the United States of America.
You can read ‘The Legend of Sleepy Hollow’ here before proceeding to our plot summary and analysis below.
‘The Legend of Sleepy Hollow’: plot summary
In the Dutch settlement of Tarry Town in New York State there is a secluded grove known as Sleepy Hollow. Rumours say that Sleepy Hollow is haunted. The most famous ghost of those sighted is a figure known as the Headless Horseman, which is thought by some to be the ghost of a Hessian soldier whose head had been shot from his body by a cannonball during a battle of the American Revolution. The story is set just after the end of the American War of Independence, in the late eighteenth century.
In Tarry Town there lives a tall, lean schoolmaster named Ichabod Crane. Crane takes a shine to a young woman, Katrina Van Tassel, not least because her father is a wealthy man. Crane is something of an outsider in the community, with very little money of his own and no family. He sees marriage to a wealthy woman as his route out of relative poverty. However, another man, Abraham Von Brunt (known as ‘Brom Bones’), also has designs on Katrina. Brom Bones is a hero to the people of Sleepy Hollow, ‘full of mettle and mischief’.
One night, Crane attends a harvest party at the Van Tassels’ farm and listens to ghostly legends told by Brom Bones and others. Crane fails to win Katrina’s hand in marriage, and rides home, his superstitious imagination working overtime following the ghostly accounts he had heard at the party. Ichabod encounters what appears to be the ghostly headless horseman, which is really (almost certainly) Brom Bones in disguise, playing a prank on Crane. Bones had brought a pumpkin with him and hurls it at Crane, who believes it to be the ghost’s severed head.
Ichabod Crane disappears from Sleepy Hollow, and Katrina and Brom Bones arrange to be married. Nobody knows what happened to Crane, but the old Dutch wives of the town believe he was taken away by spirits.
‘The Legend of Sleepy Hollow’: analysis
‘The Legend of Sleepy Hollow’ is a story shot through with peculiarly American detail, making it the New World’s answer to the European tales of the Brothers Grimm. Indeed, Irving was influenced by German folk tales for both this and ‘Rip Van Winkle’, and he actually wrote the story while living in Birmingham, England.
But what does the story mean? Should we view it as an out-and-out ‘Gothic’ tale, or as a more realist tale which merely draws upon Gothic elements? Part of the problem is that we cannot be entirely sure that the ghost of the headless 
horseman whom Crane encounters towards the end of the narrative really is just Brom Bones in disguise, determined to give his love rival a fright and clear the way for him to woo Katrina for himself. We are led to believe this, but Irving’s narrative does not confirm it at any point.
And two aspects of Irving’s story make it difficult for us to determine whether the events of the story are meant to be taken as genuinely supernatural or as a hoax perpetrated by Brom Bones. First, Irving’s narrator is the figure he uses as editor and narrator for many of his writings: Diedrich Knickerbocker. (Incidentally, that surname, which was Irving’s own invention, came to be used as a nickname for an inhabitant of New York; eventually, it inspired the name of men’s colourful trousers and, by association, the multicoloured ice-cream dessert the knickerbocker glory. Over in England, the ‘knickerbockers’ used to describe men’s clothing became shortened to ‘knickers’ and was applied to women’s underwear. Thanks, Washington Irving!)
Knickerbocker is, if not an unreliable narrator, an imperfect one: he is not omniscient, and freely admits the limits of his knowledge about the events of the story. In a Postscript, Knickerbocker claims he heard the story of ‘The Legend of Sleepy Hollow’ from someone else, who himself didn’t believe half of it. Is this tall tale meant to be taken with a pinch of salt? The effect of this is to lend the story an air of authentic oral tradition, of folklore and rumour, as if it describes a genuine event which has been passed around from teller to teller. But it also means that details are often murky or fuzzy, as Knickerbocker is hearing it second-hand (or even third-, fourth-, fifth-hand, etc.).
Here is Irving’s narrator telling us about what passes between Ichabod Crane and Katrina at the dance:
What passed at this interview I will not pretend to say, for in fact I do not know. Something, however, I fear me, must have gone wrong, for he certainly sallied forth, after no very great interval, with an air quite desolate and chapfallen. Oh, these women! these women! Could that girl have been playing off any of her coquettish tricks? Was her encouragement of the poor pedagogue all a mere sham to secure her conquest of his rival? Heaven only knows, not I!
Earlier, Knickerbocker had declared, ‘I profess not to know how women’s hearts are wooed and won.’ But now it’s not just women’s hearts or minds that he admits his ignorance of; it’s what went on between Crane and Katrina as he sought to woo her. He can only pass on tentative knowledge of what happened, and this goes for the events surrounding Crane’s eventual disappearance when the ‘headless horseman’ chases him.
The other narrative effect Irving uses to clever effect in ‘The Legend of Sleepy Hollow’ is to keep the focalisation of the story quite close to Ichabod Crane himself. Focalisation describes whose eyes we ‘see’ the story through, and although we start out viewing the gangling schoolmaster from a distance, as it were, we are soon ushered into his own superstitions and fears during that hectic horse-ride home. Look at how Irving describes the final moments before Crane disappears forever:
Just then he saw the goblin rising in his stirrups, and in the very act of hurling his head at him. Ichabod endeavored to dodge the horrible missile, but too late. It encountered his cranium with a tremendous crash, – he was tumbled headlong into the dust, and Gunpowder, the black steed, and the goblin rider, passed by like a whirlwind.
The man chasing him – probably Brom Bones – appears like a ‘goblin’ to Crane, so a goblin is how he is described, as Knickerbocker brings us close to Crane’s point-of-view as he hopelessly flees for safety. Note also, this ‘goblin’ is ‘hurling his head’, not ‘a pumpkin’ or ‘something round’, but ‘his head’ because that is how it appears to Crane in his suggestible and panicked state. Such focalisation not only pulls us into the superstitious schoolmaster’s state of mind – so that our own fear is heightened even if we suspect that a prank is being played – but also serves to define the limits of knowledge in Irving’s tale. Because we are too close to Crane, and Crane is an unreliable witness to his own experiences, we cannot be sure of what has taken place.
Like ‘Young Goodman Brown’, Nathaniel Hawthorne’s slightly later spooky tale which we have analysed here, ‘The Legend of Sleepy Hollow’ was a founding text in America’s Gothic literary history. Both stories are set in the autumn around Halloween, that date in the calendar which the United States did so much to develop into an annual rite. And ‘The Legend of Sleepy Hollow’, we should remember, is set during the early years of the United States. The headless horseman is thought by locals to be the ghost of a Hessian trooper: German soldiers who served as auxiliaries to the British Army during the American Revolutionary War. Irving’s story shows us a young country already haunted by its own past.