Ichabod Crane lives in a quiet drowsy dark town that is known for its spooky stories. Ichabod is a schoolteacher and does singing lessons for extra money. He moves around from place to place because he does not have a home. Ichabod falls in love with Katrina, the daughter of Van Tassel, because of her wealth. Ichabod fights for the love of Katrina against Brom Bones. Brom Bones plays tricks and embarrasses Ichabod. At Van Tassel's party, Ichabod had a private conversation with Katrina that did not go as planned so he leaves. As Ichabod left, Brom Bones messes with him by pretending to be the "headless horseman", as one from the stories, to run after him to scare him. Ichabod Crane left to New York because he was scared and embarrassed from what happened.

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