In 1799, New York City police constable Ichabod Crane (Johnny Deep) is facing imprisonment for going against traditional methods and favoring forensic investigation techniques, such as autopsies, considered unorthodox and unimportant at the time. Ichabod submits to deployment with his bag of tools to the Westchester County of Sleepy Hollow, New York, which has been plagued by a series of brutal slayings in which the victims have been found decapitated: Peter Van Garrett , wealthy farmer and landowner; his son Dirk; and the widow Emily Winship. Arriving in Sleepy Hollow, Crane is informed by the town's elders that the killer is not of flesh and blood, but rather an undead headless mercenary from the American Revolutionary War who rides at night on a massive black steed in search of his missing head.
Crane begins his investigation, remaining highly skeptical about the supernatural elements in the case until he actually encounters the Headless Horseman himself, who kills the town magistrate, Samuel Phillipse (Richard Griffiths), on sight. Boarding in a room at the home of the town's richest family and the Van Garretts' next of kin, the Van Tassels, Crane develops an attraction to their daughter Katrina (Christina Ricci), while he is plagued by nightmares of his mother's horrific torture when he was a child. This attraction is deeply resented by Brom van Brunt (Casper Van Dien), a suitor to Katrina, who scares Crane in a prank by posing as the Headless Horseman. Riding into the Western Woods with the orphaned Young Masbath, son of the Horseman's fifth victim Johnathan Masbath(before Magistrate Phillipse), Crane and Young Masbath come across the cave dwelling of a reclusive sorceress. She reveals the location of the gnarled Tree of the Dead, which marks the Horseman's grave, as well as his portal into the natural world from the supernatural.
Crane discovers that the ground is freshly disturbed and, digging through, discovers the Horseman's skeleton and that the skull is missing. He realizes that whoever dug up and stole the skull is the person controlling the Horseman. Just then, the Horseman's ghost bursts out of the tree and gallops towards Sleepy Hollow. Crane attempts to follow but winds up lost. The Killian family are taken by the Horseman and Brom is killed — cut in half — when trying to stop the Horseman.
Crane starts to believe that a conspiracy links all the deaths together, so he goes to the town notary James Hardenbrook (MIchael Gough) to look into Van Garrett's Last Will. Hardenbrook confesses Van Garrett had made a new will just before he died, leaving all his possessions to his new bride, Emily Winship, who Crane had learned from the late Magistrate Phillipse was pregnant at the time of her death (and thought that initially the father of the child might have killed Emily to keep the secret hidden). Crane deduces that all who knew about the new will were the victims of Horseman and that Katrina's father Baltus Van Tassel (Michael Gambon), who would have inherited the fortune, is the person holding the skull. Katrina, finding out that Crane suspects her father, burns the evidence that Crane has accumulated and tells him that she doesn't love him anymore.
In fear of the Horseman, Hardenbrook hangs himself and a town council is held in the town church. The Horseman seemingly kills Katrina's stepmother, Lady Van Tassel, and heads off to the church to get Baltus, with the townspeople filing in just as the he arrives. With the men firing muskets as he circles the church, Crane realizes the Horseman can't enter the church grounds due to it being consecrated and therefore holy. A massive fight breaks out in the church when Dr. Thomas Lancaster (Ian McDiarmid) suggests confessing for forgiveness, and is killed by Reverend Steenwyck (Jeffrey Jones), who is in turn shot by a frightened Baltus. The chaos ends only when the Horseman harpoons Baltus through a church window using a pointed church fence post attached to a rope, dragging him out and acquiring his head. The next day, Crane believes Katrina to be one who controls the Headless Horsemen and left while she was still unconscious.
As Crane is leaving Sleepy Hollow, he becomes suspicious when the hand of the corpse of Lady Van Tassel has a wound which shows signs of having been caused post-mortem. His suspicions are confirmed to be right when the real Lady Van Tassel (Miranda Richardson) emerges, alive, from the dark and shocks her step-daughter Katrina into a faint. Katrina awakens and eventually uncovers a plot revolving around revenge on the Van Garretts and land rights with the Horseman controlled by Lady Van Tassel, who sends the supernatural killer after Katrina now to solidify her hold on what she considers her property, a piece of land unjustly claimed by Baltus. She explains that the body believed to be her corpse actually belonged to the family's servant, Sarah, whom she had murdered. She also reveals that she had just murdered the mysterious witch in the Western Woods, her own sister, for her role in helping Crane and Young Masbath.
Following a fight in the local windmill and a stagecoach chase through the woods, Crane eventually thwarts Lady Van Tassel by throwing the skull to the Horseman, breaking the curse. The Horseman, no longer under Lady Van Tassel's control, simultaneously kisses and bites her, and he hoists her up on his horse, then rides to Hell taking her with him, fulfilling her end of the deal with the Devil. With the Headless Horseman menace eradicated, Crane returns home to New York with Katrina and Young Masbath, just in time for the new century.
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