Based on the classic Washington Irving short story, this is the tale of Ichabod Crane who arrives in Sleepy Hollow one October to take the position of schoolmaster in the small town. Seeing an opportunity to make his way in the world, he attempts to woo Katrina Van Tassel, the only child of a wealthy farmer. His rival in this pursuit is a rowdy local, Abraham Van Brunt, whom the townsfolk call “Brom Bones” due to his strength and tough demeanor.

As he takes his place in town, Ichabod soon learns that the town's dark history has a way of returning, and the residents of Sleepy Hollow regularly see spirits of soldiers, conjuring witches and mischievous imps in the countryside. Ghost stories permeate life in the quaint little town, and things might not be all they seem to be.

One night, as Ichabod heads back home, the shadows start to close in. With the bridge to safety in the distance, he happens across the most infamous and powerful of all Sleepy Hollow’s nightmares…