Along with Irving's companion piece "Rip Van Winkle", "The Legend of Sleepy Hollow" is among the earliest examples of American fiction with enduring popularity, especially during Halloween because of a character known as the Headless Horseman believed to be a Hessian soldier who was decapitated by a cannonball in battle.

Unable to goad Ichabod into fighting for Katrina's hand, Brom instead wages a campaign of harassment against the schoolmaster, plaguing him with a series of pranks and practical jokes.

At the party, Brom tells the story of the Headless Horseman, the notorious ghost of a Hessian trooper decapitated by a cannonball during the Revolutionary War.

The Horseman is supposedly buried in a churchyard in Sleepy Hollow and rises from his grave every night to search for his missing head but is supernaturally barred from crossing a wooden bridge that spans a nearby stream.

The next morning, Gunpowder is found eating the grass at his master's gate, but Ichabod has disappeared from the area, leaving Katrina to marry Brom Bones.

A shattered pumpkin is found near Ichabod's hat where he fell, suggesting that the severed head thrown at him was merely a jack-o'-lantern and that Crane survived the fall from Gunpowder and fled Sleepy Hollow in horror.

Usually viewed as omens of ill fortune for those who chose to disregard their apparitions, these specters found their victims in proud, scheming persons and characters with hubris and arrogance.

[4] After the Battle of White Plains in October 1776, the country south of the Bronx River was abandoned by the Continental Army and occupied by the British.

The Americans were fortified north of Peekskill, leaving Westchester County a 30-mile stretch of scorched and desolated no-man's-land, vulnerable to outlaws, raiders, and vigilantes.

[6] According to another hypothesis, Irving could have drawn the figure of the "headless rider" from German Silesian literature, precisely from the Chronicle of Sprottau (since 1945 Polish Szprotawa) by J.G.