In the year 1799 a twenty four year old officer named Ichabod Crane has been told by his superiors about a string of decapitation deaths in Westchester County. When he arrives in the hamlet of Sleepy Hollow he learns about the deaths of Peter Van Garrett, his son and the widow Emily Winship. While staying with Master Van Tassel he speaks of the legend of a Hessian Horseman that was beheaded by American rebels. Crane is skeptical on the thought of a supernatural killer until he encounters the Headless Horseman riding his black stead.
Crane witnesses the beheading of the local magistrate Samuel Phillipse. After that ordeal he returns to the home of the Van Tassels where he is boarding. While staying with Van Tassel family, he is captivated by Lady Van Tassel's daughter Katrina. She takes him to see the local witch to find answers about the Headless Horseman. The witch tells Crane to seek out the Tree of the Dead which is the gateway between the world of the living and the spirit world.
Aided by the boy Young Masbath whose father was killed by the Headless Horseman, the duo sets out into the Western Woods to find the Horseman's grave known as the Tree of the Dead. While there, they discover that there is no trace of the Horseman's skull in the tree. He begins to investigate the Van Garrett land records on the previous tenants before the Van Tassels to discover that Lady Van Tassels was related to the Archer Family who were evicted.
At the local church where the townspeople gathered to stay safe from the Horseman only to discover the killer has followed them to take another victim. He attacked Reverend Steenwyck beheading him right in front of Katrina Van Tassel leaving her in a state of shock. When Crane and Young Masbath arrive at the aftermath of the attack they discover Katrina is missing amongst the survivors. Meanwhile she is taken to the flour mill by her stepmother, when she awakes she discovers that her stepmother Lady Van Tassel is controlling the Horseman.
She learns that her stepmother and her twin sister were evicted from their land by Peter Van Garrett during the war. Crane discovers the truth behind the murder plot and decides the Horseman's reign of terror. After battling the Horseman on a carriage chase through the Western Woods, in the final battle Crane throws the skull back to the Headless Horseman.
In a twist of fate Lady Van Tassel is claimed by the Horseman and taken back to Hell where she belongs. When it was finally over Crane takes Katrina and Young Masbath back to New York with him to ring in the 19th Century.
FOX has been developing a new pilot based on Washington Irving’s short story, Sleepy Hollow, and Orlando Jones and Katia Winter have just joined the cast. The show is described as a “modern-day supernatural thriller” based on the legend of the Headless Horseman who haunted Ichabod and Sleepy Hollow in the popular story. Multiple films have been made based on the story, including the enjoyably bad "Sleepy Hollow" starring Johnny Depp, Christina Ricci and Christopher Walken.