Ichabod Crane, a lean, lanky and extremely superstitious schoolmaster from Connecticut, who competes with Abraham Van Brunt, the town rowdy, for the hand of 18-year-old Katrina Van Tassel, the daughter and sole child of a wealthy farmer, Baltus Van Tassel. Crane, a Yankee and an outsider, sees marriage to Katrina as a means of procuring Van Tassel’s extravagant wealth. Bones, the local hero, vies with Ichabod for Katrina’s hand, playing a series of pranks on the jittery schoolmaster, and the fate of Sleepy Hollow’s fortune weighs in the balance for some time. The tension between the three is soon brought to a head. On a placid autumn night, the ambitious Crane attends a harvest party at the Van Tassels’ homestead. He dances, partakes in the feast, and listens to ghostly legends told by Brom and the locals, but his true aim is to propose to Katrina after the guests leave. His intentions, however, are ill-fated.
After having failed to secure Katrina’s hand, Ichabod rides home through the woods between Van Tassel’s farmstead and the Sleepy Hollow settlement. As he passes several purportedly haunted spots, his active imagination is engorged by the ghost stories told at Baltus’ harvest party. After nervously passing under a lightning-stricken tulip tree purportedly haunted by the ghost of British spy Major André, Ichabod encounters a cloaked rider at an intersection in a menacing swamp. Unsettled by his fellow traveler’s eerie size and silence, the teacher is horrified to discover that his companion’s head is not on his shoulders, but on his saddle. In a frenzied race to the bridge adjacent to the Old Dutch Burying Ground, where the Hessian is said to “vanish, according to rule, in a flash of fire and brimstone” upon crossing it, Ichabod rides for his life, desperately goading his temperamental plow horse down the Hollow. However, to the pedagogue’s horror, the ghoul clambers over the bridge, rears his horse, and hurls his severed head into Ichabod’s terrified face.