Ichabod Crane, a lanky and superstitious man and school teacher from the North, is vying for the hand of Katrina Van Tassel who happens to have another suitor named Abraham "Brom Bones" Van Brunt. Crane has ill intentions in winning the hand of Katrina and Brom decides to try to spook the school teacher out of Sleepy Hollow through a series of pranks.

One autumn night, at the annual harvest party at the Van Tassel farmstead, Ichabod finally comes up with the courage to propose to Katrina, but he is rejected and leaves the party feeling sad and heavy hearted. As he is riding home, Ichabod encounters many strange things and cannot discern between what is real and what he can attribute an overactive imagination. He suddenly encounters a very real apparition of none other than the headless horseman, a soldier said to have lost his head during the Revolutionary War who rides nightly searching for it.

Ichabod rides furiously for the grounds near the cemetery where it is said that the Headless Horseman will disappear in a flash of fire. Ichabod never makes it to the cemetery or back home and is never heard from again. Was he spirited away by the Headless Horseman, or could some other force be to blame for the untimely disappearance?