The Legend of Sleepy Hollow

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 numbers and citation info for the quotes below refer 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:

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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:

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Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam, quis nostrud exercitation ullamco laboris nisi ut aliquip ex ea commodo consequat. Duis aute irure dolor in reprehenderit in voluptate velit esse cillum dolore eu fugiat nulla pariatur. Excepteur sint occaecat cupidatat non proident, sunt in culpa qui officia deserunt mollit anim id est laborum.

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:

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Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam, quis nostrud exercitation ullamco laboris nisi ut aliquip ex ea commodo consequat. Duis aute irure dolor in reprehenderit in voluptate velit esse cillum dolore eu fugiat nulla pariatur. Excepteur sint occaecat cupidatat non proident, sunt in culpa qui officia deserunt mollit anim id est laborum.

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:

Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam, quis nostrud exercitation ullamco laboris nisi ut aliquip ex ea commodo consequat. Duis aute irure dolor in reprehenderit in voluptate velit esse cillum dolore eu fugiat nulla pariatur. Excepteur si

Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam, quis nostrud exercitation ullamco laboris nisi ut aliquip ex ea commodo consequat. Duis aute irure dolor in reprehenderit in voluptate velit esse cillum dolore eu fugiat nulla pariatur. Excepteur sint occaecat cupidatat non proident, sunt in culpa qui officia deserunt mollit anim id est laborum.

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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
...as 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)