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Ichabod Crane is the story’s protagonist. He is “tall, but exceedingly lank, with narrow shoulders, long arms and legs, hands that dangled a mile out of his sleeves, feet that might have served for shovels, and his whole frame most loosely hung together” (9). Since Irving goes to great lengths to paint a picture of Ichabod’s awkward appearance, the prospect of the imposing Headless Horseman wearing Ichabod’s tiny head is comical.
Irving describes Ichabod as looking like a scarecrow or “the genius of famine” (9). This description is ironic because despite having an enormous appetite, Ichabod is always hungry. One of his key motivations in Sleepy Hollow is to find as much good food as possible, and this desire brings him into the homes of his new neighbors, where he hears ghost stories about the Headless Horseman.
Ichabod is from Connecticut; his age is unspecified. As a schoolmaster, Ichabod is strict, even beating his students with a birch switch if they misbehave. The narrator notes that Ichabod is not unfair and only disciplines the stronger, more wayward children. In addition to teaching, Ichabod does odd jobs in the community that help him make a living.
Aside from his appearance, the most salient detail about Ichabod is his strong belief in superstition. One of his only possessions is Cotton Mather’s History of New England Witchcraft. He loves exchanging ghost stories with the locals, and his impressionable nature makes him believe wholeheartedly in the Headless Horseman. Irving constructs Ichabod Crane as a ridiculous caricature of a man, making his disappearance more fascinating than tragic.
Brom Bones is the story’s antagonist and Ichabod’s rival in pursuing Katrina Van Tassel. Brom is renowned for his feats of strength, expert horsemanship, and mischievous nature. He is a burly man with curly black hair, and his personality is a mixture between “fun and arrogance” (31). While others fear the Headless Horseman, Brom’s tale of racing the Headless Horseman for a bowl of punch shows that he does not take the story seriously (63). If he indeed did dress up as the Horseman to chase Ichabod away, he knows that the superstitions of those around him will make them less likely to suspect him. In the end, Brom marries Katrina. The narrator implies that Brom knows what happened to Ichabod, though he never reveals the secret.
Katrina Van Tassel is the 18-year-old daughter of Baltus Van Tassel, the wealthiest farmer in Sleepy Hollow. Irving heavily sexualizes her, describing her as “plump as a partridge; ripe and melting and rosy-cheeked as one of her father’s peaches” (23). She is a coquette (flirt), and the narration implies that she dresses suggestively, in “a mixture of ancient and modern fashions, as most suited to set off her charms” (24). She attends Ichabod’s singing lessons and entertains him at her father’s house.
Katrina is a plot catalyst. Ichabod’s interest in her prompts him to go to Van Tassel’s party, and Brom’s disdain for Ichabod as his rival prompts Brom to scare Ichabod away. Katrina rejects Ichabod shortly before the story’s climax, completing the story’s romantic subplot and allowing the focus to return to the ghost story. Katrina’s only act of agency, perhaps, is leading Ichabod on to make Brom jealous. Like everyone else in town, she is unconcerned with Ichabod’s disappearance. She likes Brom Bones and seems happy to marry him in the end.
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By Washington Irving