The Legend of Sleepy Hollow

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Headless Horseman Character Analysis

Also known as the Galloping Hessian of the Hollow. The Dutch wives of Sleepy Hollow especially enjoy telling ghost stories about the Headless Horseman, the ghost of a Hessian trooper (a German mercenary who fought for the British) whose head was blown off during the Revolutionary War. As the story goes, since his death, he leaves the churchyard where his body is buried each night and gallops off in search of his head.

Headless Horseman Quotes in The Legend of Sleepy Hollow

The The Legend of Sleepy Hollow quotes below are all either spoken by Headless Horseman or refer to 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.

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Headless Horseman Character Timeline in The Legend of Sleepy Hollow

The timeline below shows where the character Headless Horseman appears in The Legend of Sleepy Hollow. The colored dots and icons indicate which themes are associated with that appearance.
Main Story
History and Storytelling Theme Icon
Reality, Imagination, and the Supernatural Theme Icon
War and Battle Theme Icon
...stories about their region. One of the most pervasive tales is that of the Headless Horseman, who rides by on horseback through the night—supposedly it is the ghost of a Hessian... (full context)
Reality, Imagination, and the Supernatural Theme Icon
It’s not only the inhabitants of Sleepy Hollow who tend to see the Headless Horseman riding by at night, but also anyone who stays in the valley for awhile, and... (full context)
History and Storytelling Theme Icon
Reality, Imagination, and the Supernatural Theme Icon
...Hollow and the fields, brooks, and haunted houses throughout it as their setting. The Headless Horseman, or Galloping Hessian of the Hollow, is one of them. Ichabod joins in with stories... (full context)
Reality, Imagination, and the Supernatural Theme Icon
...for those of a specter behind him, and a gust of wind for the Headless Horseman following him. But by morning, daylight cures him of all his fears. (full context)
History and Storytelling Theme Icon
Reality, Imagination, and the Supernatural Theme Icon
War and Battle Theme Icon
...Major André, the woman in white who haunts Raven Rock, and, above all, the Headless Horseman who has been recently spotted tethering his horse to churchyard graves. The church is isolated,... (full context)
Reality, Imagination, and the Supernatural Theme Icon
War and Battle Theme Icon
The guests tell of old Brouwer, who didn’t believe in ghosts until he met the Horseman on his way back from Sleepy Hollow. They raced each other on horseback until reaching... (full context)
Reality, Imagination, and the Supernatural Theme Icon
War and Battle Theme Icon
...trots along behind him. Ichabod immediately thinks of Brom Bones’ story about racing the Headless Horseman, but when he quickens his pace, his follower does as well. As they race up... (full context)
Reality, Imagination, and the Supernatural Theme Icon
War and Battle Theme Icon
...about the event, and conclude that Ichabod must have been carried off by the Headless Horseman. Since he didn’t have family or any debt, people soon forget about him. (full context)
History and Storytelling Theme Icon
Reality, Imagination, and the Supernatural Theme Icon
...generally the most knowledgeable in the village, insist that Ichabod was carried away by the Horseman. The story becomes a favorite one in the neighborhood, and since the bridge is feared... (full context)