The strange little tale of Ichabod Crane - local schoolmaster in the small village of Sleepy Hollow. He has an interest and firm belief in witchcraft and listens to all the local ghost stories - the most startling being the tale of the Headless Horseman - who lingers around the small church and races along the pathways in search of his missing head, spurring his horse to great speeds.
Ichabod tries to court the lovely Katrina Van Tassel, the heiress to a large farm but finds he has competition in the form of Brom Bones - a lad with a strong reputation - a legend almost in his own right. Crane becomes the victim of pranks as Bones tries to make him look a fool in front of Van Tassel.
Katrina's father throws a "merry making" for the villagers and Crane attends - borrowing a horse from the farmer with which he is staying. At the end of the evening he leaves the Van Tassel farm - greatly upset, by what we do not know specifically but it is intimated that Katrina has turned Ichabod down - prefering Bones. It is all too late that Crane realises how late it is an happens across the headless horseman, trying to out run him - and trying to dodge the head that the horseman throws at him. The next day no trace is found of Crane apart from his hat found next to a pumpkin.
At the end of tale you are left to wonder - has Ichabod encountered the Headless Horseman? Crane is never again seen in Sleepy Hollow - but news trickles back that he moved away - or has he and why does Brom Bones seem to know more about Cranes fate?