The story The Legend of Sleepy Hollow takes place after the American Revolution, mainly 1780. Sleepy Hollow is a small valley in New York where Dutch settlers acculturated the area, which perhaps influenced Irving. Historically, the story is not too far from where the Salem Witch Trials took place, which may have also added an aura of mystery and superstition. The headless horseman, supposedly the ghost of a Hessian soldier in the Revolutionary War "rides forth to the scene of battle in nightly quest of his head.", and creates the feeling of mythology to an American event. In Irving’s times, his story may have added a sense of realism because of the relatability.
Sleepy Hollow is about two miles from Tarry Town, New York. The residents of Sleepy Hollow seem to be under a drowsy trance and highly influenced by the supernatural. The setting continues to be persistent of the mood when it’s described as quiet at day and mystical at night where “stars shoot and meteors glare oftener across the valley than in any other part of the country”. Sleepy Hollow also seems to be isolated, and repetitive in landscape, as if it were a mask for the supernatural. The setting conveys the mood to such a high degree that the attitude of the story is detailed through deep use of location rather than feelings.
Ichabod Crane is the protagonist of The Legend of Sleepy Hollow; already superstitious, his nervous behavior intensifies living in Sleepy Hollow. He is egotistical and self-praises himself in the belief that his love interest is lucky that he woos over her. Being a pedagogue, Ichabod has an exceptional imagination, but would rather use it for thoughts of gluttony and greed; slobbering over the thought of indulgences and riches. After a night of partying, Ichabod becomes enwrapped in the thoughts of the supernatural; making himself weary and panicky. No one’s quite sure what happened to him.