In "The Legend of Sleepy Hollow," Ichabod Crane's hat is discovered near the bridge over the brook, next to the remains of a shattered pumpkin. The only thing Irving tells the reader about this pumpkin is that Brom Bones "always burst[s] into a hearty laugh" whenever it is mentioned, leading to a suspicion that he knows something about Ichabod's disappearance that he does not tell anyone.

It is evidence of Irving's skill as a storyteller that most readers construct for themselves a tale he never explicitly tells. It is implied that when Ichabod leaves the party at the Van Tassels' home, Brom Bones draws his cloak up over his head and rides after him, to impersonate a headless horseman and terrify Ichabod. He carries a pumpkin, which is intended to look like his head, and, at the crucial moment, throws the pumpkin at Ichabod, knocking him off his horse. The answer to the question, therefore, is that the headless horseman does not exist. Brom Bones carries a pumpkin to look as though he is the headless horseman and to throw at Ichabod. However, although this is the solution shown in several film versions of the story, it is never explicitly stated by the author, who leaves it to the reader to make these connections.