The story is set in 1790 in the countryside near the former Dutch settlement of Tarry Town, in a secluded glen known as Sleepy Hollow. It relates the tale of Ichabod Crane, a lean, lanky, superstitious schoolmaster from Connecticut. Ichabod intends to woo Katrina Van Tassel, the daughter of a wealthy farmer, in order to procure her family's riches for himself. He competes for her affection with Abraham "Brom Bones" Van Brunt, the town rowdy. 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.
One autumn night, Ichabod is invited to attend a harvest party at the Van Tassel homestead. 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.
Ichabod proposes to Katrina, but she rejects his advances. He leaves the party heartbroken and rides home on a borrowed plough horse named Gunpowder. He encounters a cloaked rider and believes it to be the Headless Horseman. Ichabod rides for his life, desperately goading Gunpowder down the Hollow. The Horseman rears his horse and hurls his severed head directly at Crane, knocking him off his horse.
The next morning, Gunpowder is found eating the grass at his master's gate, but Ichabod has mysteriously disappeared from the area, leaving Katrina to marry Brom Bones. Although the true nature of both the Headless Horseman and Ichabod's disappearance that night are left open to interpretation, the story implies that the Horseman was really Brom in disguise, using a Jack-o'-lantern as a false head, and suggests that Crane survived the fall from Gunpowder and immediately fled Sleepy Hollow in horror.
