When the dreaded Headless Horseman returns to modern-era Sleepy Hollow in hopes of collecting some craniums, it's up to a teen who just happens to be a direct descendent of Ichabod Crane to put a stop to the headless happenings in this terrifying tale from director Kyle Newman. High school senior Ian Cranston (Kevin Zegers) is a newcomer to the town of Sleepy Hollow, and when Ian sets his sights on pretty cheerleader Karen (Kaley Cuoco) he soon incurs the wrath of her boyfriend, arrogant star quarterback Brody (Nick Carter). As Halloween approaches and Ian has a strange encounter with local gravedigger Clause (Stacy Keach), the tales of the Headless Horseman take an ominous slant as a pair of students go missing and Ian is told that he is a direct descended of the legendary Ichabod Crane. When the real Headless Horseman makes a shocking appearance at the annual Halloween hayride, Ian discovers that he is the only hope to save his father Carl (Judge Reinhold) from a grim fate at the hands of the vengeful entity.