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.