In 1799 America, Peter Van Garrett writes and seals a series of documents, before fleeing the small Dutch hamlet of Sleepy Hollow with his son, Dirk. On the road, their carriage is overtaken by a lone rider who beheads Dirk, and follows Peter into a cornfield, where he is slain as well. Elsewhere in New York City, mild-mannered constable Ichabod Crane (Johnny Depp) comes at odds with his superiors due to his persistent arguments in favor of integrating modern scientific procedures into the American justice system. Crane, who suffers from severe religious trauma (caused by the torture and murder of his mother, a practitioner of benign witchcraft, at the hands of his father, a sadistic religious fanatic) abhors the torturous methods used to solve crimes, and advocates for early forensic science in its stead. To this end, the Burgomaster (Christopher Lee) dispatches him to Sleepy Hollow to investigate the Van Garretts' murders, as well as the murder of the local widow Emily Winship, who was also found beheaded. Arriving in Sleepy Hollow, Crane meets Katrina Van Tassel (Christina Ricci) and her suitor Brom (Christopher Van Dien), and is welcomed by Katrina's father, Baltus (Michael Gambon), and stepmother, Mary (Miranda Richardson). Upstairs, Crane discusses the murders with Baltus and the other town elders: Reverend Steenwyck (Jeffrey Jones), Doctor Lancaster (Ian McDiarmid), Magistrate Samuel Philipse (Richard Griffiths), and Notary James Hardenbrook. The town believes that the murders are the work of Sleepy Hollow's local ghost story, the Headless Horseman. Baltus explains that the Horseman was once a bloodthirsty Hessian mercenary (Christopher Walken) who fought in the American revolutionary war, riding a great black steed and beheading his victims with a sword. When the Horseman was finally beaten, he was beheaded with his own sword and buried in the Hollow's western woods. The town believes the Horseman to have returned from the grave to slaughter its inhabitants, but Crane remains confident that the murderer is a mortal. The next morning, a fourth victim is found: Van Garrett's servant, Jonathan Masbath. Investigating the scene of the crime, Crane discovers that the wound was instantly cauterized, which the elders believe to be a sign of demonic force. At Masbath's funeral, Crane accepts his son, Young Masbath, into his service, and exhume the bodies of the Horseman's victims on a tip from Magistrate Philipse. Discovering a stab wound on Winship's body, Crane performs an autopsy on the widow and discovers that she was pregnant. That night, Crane is attacked by a headless rider in black, who turns out to be Brom playing a prank on him. Katrina takes Crane to the ruins of her family's old cottage, where the two begin to bond, and gives him a small spell-book for protection. Magistrate Philipse tries to flee, but is confronted by Crane, who interrogates him regarding his knowledge of Winship's pregnancy. The Headless Horseman suddenly appears and kills Philipse in front of Crane, riding into the woods with his head. Despite his initial terror, Crane volunteers to lead an expedition to the western woods, with Young Masbath the only one volunteering to accompany him. In the woods, Masbath mentions an argument that his father overheard between Peter Van Garrett and his son, and the two stumble upon the home of an old crone, who directs them to find the Headless Horseman's grave beneath the Tree of the Dead. Encountering Katrina along the way, the three reach the tree, which Crane deduces to be a gateway between the worlds of the living and the dead. Finding the Horseman's grave disturbed, Crane exhumes the body to find the skull missing. At that moment, the Horseman bursts from the base of the tree and rides for Sleepy Hollow, where he kills midwife Beth Killian (Claire Skinner) and her family. Unable to kill the Horseman, Brom is killed and Crane is stabbed. Recovering at the Van Tassels' house, Crane deduces that someone is using the Horseman's skull to summon and control him, and opens up to Katrina about his religious trauma. Suspecting a conspiracy, he confronts Notary Hardenbrook, and discovers that Peter Van Garrett secretly married Emily Winship, and made a new will that named the widow and her unborn child his sole beneficiaries. Realizing that Baltus stands the most to gain from the murders, Crane names him the prime suspect, as all those beheaded are either witnesses or beneficiaries to Van Garrett's will. That evening, Crane discovers the sign of the Evil Eye under his bed, and follows a hooded figure into the woods, who he discovers to be Lady Van Tassel in the middle of a sexual rendezvous in which she ritualistically cuts open her hand. The next day, Katrina burns the evidence against her father, and spurns Crane when he confronts her. Crane learns that Notary Hardenbrook has taken his own life. Reverend Steenwyck holds a meeting to discredit Crane, when Baltus rushes in declaring that the Horseman has killed Lady Van Tassel. The townsfolk shelter in the church, as the Horseman cannot enter. Steenwyck kills Doctor Lancaster when the latter confesses their conspiracy to Baltus, who shoots and kills Steenwyck in self-defense. The Horseman impales Baltus with a makeshift harpoon and drags him out of the church, beheading him. Crane finds that Katrina has drawn a large Evil Eye sigil on the church floor. Believing her to be in control of the Horseman, and unable to bring himself to accuse her, Crane leaves Sleepy Hollow. Crane discovers that the Evil Eye is actually a sigil of protection, and discovers the wound on "Lady Van Tassel's" body to have been inflicted post-mortem: the real Lady Van Tassel, having faked her death, abducts Katrina. At the town's old windmill, she reveals her true heritage as the daughter of an impoverished family who had been evicted by the Van Garrets. Making a pact with Satan, she summoned the Headless Horseman to kill those who had wronged her, and manipulated her way into the Van Tassel family while coercing the other elders into her plot. Having killed all beneficiaries and witnesses - as well as her sister, the crone who aided Crane and Masbath - Lady Van Tassel summons the Horseman to kill Katrina, the final obstacle between her and both the Van Garrett and Van Tassel estates. Crane arrives in the nick of time to save Katrina and Young Masbath, and the three destroy the windmill in an attempt to kill the Horseman. Fleeing to the Tree of the Dead, they are intercepted by Lady Van Tassel, who shoots Crane. Crane survives thanks to Katrina's spell-book taking the bullet, and manages to retrieve the Horseman's skull from Lady Van Tassel's possession. He returns it to the horseman just as Katrina is about to be killed, freeing him from his curse. The Horseman's head is restored, and he rides back to Hell, taking Lady Van Tassel with her. With the Headless Horseman's rampage ended, Crane, Katrina, and Young Masbath return to New York City.
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