The Legend of Sleepy Hollow

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Head of the Headless Horseman Symbol Icon

The Headless Horseman, of course, is a major character in “The Legend of Sleepy Hollow.” But the ghostly rider—and, especially, his head—also symbolize the tension between reality and imagination, between the natural and the supernatural, held by many of the townspeople. The Horseman is fixed in historical fact: there were, indeed, many Germans or “Hessians” hired by the British to fight against the American army during the Revolutionary War. Indeed, though the townspeople’s stories about the Galloping Hessian may be ghost stories, it hasn’t been long since a real Hessian rider (one alive and with a head) could provoke fear in them for good reason—as the enemy. By becoming headless, the horseman can become nestled within society’s cultural and imaginative traditions, even while remaining based in history.

But in other ways, the horseman symbolizes Ichabod’s less defensible inability to separate fiction and fact. Indeed, it loses its head just as Ichabod, more metaphorically, loses his each time he returns home spooked by the Dutch ghost stories. Brom Bones takes advantage of this lack of reason. Brom uses his head—both intellectually in plotting and strategizing, and practically in hurling a “head” at Ichabod.

Head of the Headless Horseman Quotes in The Legend of Sleepy Hollow

The The Legend of Sleepy Hollow quotes below all refer to the symbol of Head of the Headless Horseman. For each quote, you can also see the other characters and themes related to it (each theme is indicated by its own dot and icon, like this one:
History and Storytelling Theme Icon
). Note: all page and citation info for the quotes below refers to the Penguin Classics edition of The Legend of Sleepy Hollow published in 1999.
Main Story Quotes

The whole neighborhood abounds with local tales, haunted spots, and twilight superstitions; star shoot and meteors glare oftener across the valley than in any other part of the country, and the nightmare, with her whole ninefold, seems to make it the favorite scene of her gambols. The dominant spirit, however, that haunts this enchanted region, and seems to be commander-in-chief of all the powers of the air, is the apparition of a figure on horseback, without a head.

Related Characters: Diedrich Knickerbocker (speaker), Headless Horseman
Related Symbols: Head of the Headless Horseman
Page Number: 273
Explanation and Analysis:

Irving opens his tale by describing in detail the setting of Sleepy Hollow, which is located in the Hudson Valley in upstate New York—an area that, in the 18th century, was almost entirely settled by the Dutch and their descendants. This passage is a combination of careful, objective description and fanciful storytelling, which sets the tone for the rest of the story, in which the boundaries between fact and fiction, between history and storytelling, are not always clear.

According to Knickerbocker (the narrator), this setting is ideally suited for a supernatural tale for several reasons. In some ways, he seems to suggest that the inhabitants of the town are simply more likely than the general population to swap ghost stories and to believe fantastical tales. This would situate his story within such a tradition. However, he also implies that there is indeed something in the very air or "spirit" of the setting that is supernatural—the shooting stars, and the meteors glaring across the sky. In this sense, Knickerbocker is merely a historian, chronicling the stories of a particular region. 


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The story was immediately matched by a thrice marvelous adventure of Brom Bones, who made light of the galloping Hessian as an arrant jockey.

Related Characters: Diedrich Knickerbocker (speaker), Brom Bones , Headless Horseman
Related Symbols: Head of the Headless Horseman
Page Number: 290
Explanation and Analysis:

Many of the guests at the Van Tassel party are discussing the most famous superstition of the region, that of the Headless Horseman, who was killed in the Revolutionary War and now gallops around chasing anyone who crosses his path. They have just related the story of old Brouwer, who didn't believe in ghosts until he met the Horseman one night and was chased by him, ending up being hurled into a stream.

Brom Bones, as usual, seems entirely unaffected by the frightening tales swapped by the others. He takes the opportunity to remind everyone of his own prowess as a horseman and of his inability to be conquered even by a malicious ghost. Only by the Horseman vanishing at the last minute, Brom claims, did he fail to capture and unseat him. Brom thus makes clear to Ichabod, among others, that he is not someone to be trifled with. However, his "making light" of the situation also suggests that he has escaped at least some of the bewitching influence of the region. By making fun of the Headless Horseman rather than duly expressing awe and fear of the apparition, like the others, he shows himself to be firmly anchored in reality and factual accounts of history—in other words, seemingly not a "true" citizen of Sleepy Hollow.

He saw the walls of the church dimly glaring under the trees beyond. He recollected the place where Brom Bones’s ghostly competitor had disappeared. “If I can but reach that bridge,” though Ichabod, “I am safe.”

Related Characters: Diedrich Knickerbocker (speaker), Ichabod Crane, Brom Bones
Related Symbols: Head of the Headless Horseman
Page Number: 294
Explanation and Analysis:

After leaving the party, Ichabod is confronted by a towering figure on horseback. Soon, with dread, he realizes that it is a headless body on a horse carrying its head in its saddle. The horseman pursues Ichabod through the dark paths and towards the church. Ichabod remembers this church from the story told by Brom Bones: it was there that the horseman had disappeared, so it is there that he believes he will be safe.

Ichabod thus is shown once again to embrace the tales told by fellow Sleepy Hollow inhabitants as historical truth, even though he knows that Brom Bones is prone to bragging. Although he mistrusts Brom Bones as a competitor for Katrina Van Tassel, Ichabod is credulous enough to accept his story, especially since the tale has been echoed in other versions by so many other guests at the party. These tales have become Ichabod's own reality, and he acts for his own safety in line with this reality.

In one part of the road leading to the church was found the saddle trampled in the dirt; the tracks of horses’ hoofs deeply dented in the road, and evidently at furious speed, were traced to the bridge, beyond which, on the bank of a broad part of the brook, where the water ran deep and black, was found the hat of the unfortunate Ichabod, and close beside it a shattered pumpkin.

Related Characters: Diedrich Knickerbocker (speaker), Ichabod Crane
Related Symbols: Head of the Headless Horseman
Page Number: 295
Explanation and Analysis:

The day following the Van Tassel party, Ichabod Crane cannot be found anywhere, and a search party fails to turn him up. Knickerbocker describes the evidence that they do find, much of which the reader can piece together as belonging to Ichabod's escapade the night before. It is apparent that Ichabod was there, since his hat must have flown off.

The shattered pumpkin, however, is noted in the narrative without any further explanation being attached to it. It is up to the reader to recall that the headless horseman had hurled his "head" at Ichabod, who fell to the ground, and to imagine what that "head" might be. Of course, the fact that Knickerbocker refrains from interpreting the scene means that we cannot know for sure. But significantly, the story does not draw to a close with Ichabod's immaturity and wild imagination being revealed as a fraud, while fact-based reality wins out. Instead, the story leaves us with a historical, material possibility coexisting with the supernatural explanation that Ichabod would have embraced.

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Head of the Headless Horseman Symbol Timeline in The Legend of Sleepy Hollow

The timeline below shows where the symbol Head of the Headless Horseman appears in The Legend of Sleepy Hollow. The colored dots and icons indicate which themes are associated with that appearance.
Main Story
Reality, Imagination, and the Supernatural Theme Icon
War and Battle Theme Icon well. As they race up a hill, Ichabod, horrified, realizes that the horseman is headless, and carries his head upon his saddle. The two sprint along the road, until Gunpowder... (full context)
Reality, Imagination, and the Supernatural Theme Icon
War and Battle Theme Icon
...reaches the other side, but as he looks back he sees the figure hurl his head at him. Ichabod fails to dodge it and it crashes into his own head. He... (full context)