The story is set in the Dutch settlement of Tarry Town (which is now Sleepy Hollow, Westchester County, New York, United States), near a sequestered glen called Sleepy Hollow, around the year 1787. It tells the story of Ichabod Crane, a priggish schoolmaster from Connecticut who is scared away from town by Abraham "Brom Bones" Van Brunt, his rival in love for the hand of eighteen-year-old Katrina Van Tassel, daughter of Baltus Van Tassel and a fifth-generation Dutch immigrant herself. The legend featured in the story is that of the Headless Horseman or Galloping Hessian of the Hollow, the ghost of a Hessian trooper who lost his head to a canon-ball during "some nameless battle" of the American Revolutionary War and who stalks Sleepy Hollow in search of a replacement head. The denouement of the fictional tale is set at the lower bridge in the real location of Sleepy Hollow Cemetery.

Notable film adaptations include:

• The Adventures of Ichabod and Mr. Toad directed by James Algar, Clyde Geronimi and Jack Kinney, first released on October 5, 1949. It is an animated version of the story, accompanied by an animated version of Kenneth Grahame's The Wind in the Willows and produced by the Walt Disney Company. It is somewhat darker than the original story and whether the visualy impressive Horseman is a ghost or a disguise is left somewhat unclear.
• Sleepy Hollow directed by Tim Burton, first released on November 17, 1999. A movie adaptation which takes many liberties with the plot and characters. Burton cited the Disney film as an influence, but his version is considerably darker. Christopher Walken played the Horseman.