Ichabod Crane (JOHNNY DEPP) is a late 18th century constable whose forensic science investigations into crimes are not only ahead of their time, but also aren't well-received by the more cut and dried judicial system with which he must work.
As such, a local magistrate (CHRISTOPHER LEE) sends Crane to investigate the report of several murders in upstate New York, where the victims have been beheaded. Arriving in the sleepy town of Sleepy Hollow, Crane meets its wealthiest citizen, Baltus Van Tassel (MICHAEL GAMBON), his second wife, Lady Van Tassel (MIRANDA RICHARDSON), and their daughter, Katrina (CHRISTINA RICCI), a young beauty who's immediately taken with him, arousing the suspicions of her suitor, Brom (CASPER VAN DIEN).
Nevertheless, Crane has more important issues to attend to and thus meets with many of the local town leaders including Reverend Steenwyck (JEFFREY JONES), Doctor Lancaster (IAN McDIARMID) and
Notary Hardenbrook (MICHAEL GOUGH). They inform him that the grisly deaths are at the hands of the ghost of a Hessian horseman (CHRISTOPHER WALKER) who had a thing for beheading others before meeting a similar demise many years earlier.
Being a man of science, Crane doesn't believe any of this, but after seeing the work of the headless horseman firsthand, he goes into immediate shock, dredging up memories of his mother (LISA MARIE) and her death at the hands of his preacher father. Upon recovering and being accompanied by a recently orphaned boy, Masbath (MARC PICKERING), Crane sets out to figure out exactly what's going on.
Discovering that the horseman seems to have an agenda and doesn't kill at random or even when mildly provoked, Crane tries to figure out who or what controls him while ever more people meet their deaths at the end of a sharp and burning hot sword.