Irving Crane is not at all pleased with his family's move to quiet, rural Sleepy Hollow. He doesn't like having to start at a new school during his senior year. He doesn't like having to take care of his grouchy, nearly invalid grandfather. He doesn't like the way the locals make him feel like an outsider, or how the small country church doesn't make him feel welcome, or how his jock classmate Brad Brunt torments him.

But there are a few things he does like about Sleepy Hollow. For instance, he likes riding his beloved horse Gunpowder through the trails surrounding the town. He likes the beautiful Katie Tassel very much, as well as the weekends they spend together. And he likes the local tales of ghosts and hauntings, particularly the story of the Headless Horseman, a fearsome specter forever galloping up and down the hollow, searching for his lost head. He doesn't believe the stories, of course, but he does enjoy hearing them.

At least until he has to ride home through the haunted forest, late at night, alone...and he finds they might not just be stories after all...