The Headless Horseman is a character from Washington Irving’s classic short story, The Legend of Sleepy Hollow, which is in the collection of short stories in the book, The Sketchbook of Geoffrey Crayon. The story is set in 1790 and is about a man named Ichabod Crane who is a tall, gangly, and superstitious school teacher. He comes to Sleepy Hollow, which is a small part of Tarry Town, where he meets the town folk. He falls in love with an 18 year-old girl named Katrina Van Tassel. He competes for her affection with the town bully, Abraham “Brom Bones” Van Brunt. He returns home after a party at the Van Tassel house one autumn night and is pursued by the headless horseman. He is never heard from again. The headless horseman is the ghost of a Hessian mercenary. His head was shot off by a canon ball during some nameless battle of the American Revolutionary War.

The myth of the headless horseman came from a German folktale. The folktale was set in the Dutch part of Post Revolutionary New York and was recorded by the German author Karl Musaus. In this tale, an old man who lives in the area does not believe in ghosts and is taken for a ride on a horse by the headless horseman. The man is then discarded in a ditch under the bridge. The story of the headless horseman follows the patterns of many German folktales involving a chase such as Robert Burns’ Tam O’ Shanter (1790) and Bürger’s The Wild Huntsman (1796).

The Legend of Sleepy Hollow is a much beloved story that is often told during the Halloween season. The story of Sleepy Hollow has been recreated many times in different incarnations. The story has been made into many movies, TV shows, and cartoons. The most popular of these is the Disney animated short that was a part of The Adventures of Ichabod and Mr. Toad (1949). This animated movie features the voice of Bing Crosby doing voice-over work and singing the songs of the movie. Tim Burton made a live-action movie featuring the Headless Horseman, titled Sleepy Hollow, in which he was played by Christopher Walken.

The Headless Horseman is a part of American myth. He is the villain in the story The Legend of Sleepy Hollow and is a character that inspires fear. The Headless Horseman is a character with Dutch origins but has been incorporated into American folklore.