The fictional tale of the Headless Horseman is based on some true facts.
The story of the Headless Horseman takes place during the 1790s in a community referred to as ""Sleepy Hollow"" near Tarrytown, New York. Ichabod Crane (a schoolmaster from Connecticut) competes with Abraham ""Brom Bones"" Van Brunt (the local thug) for the hand of Katrina Van Tassel (daughter of a wealthy farmer). According to the story, a Hessian trooper (who lost his head to a cannonball during the American Revolution) was buried near the Old Dutch Church and was known to haunt the area every night in search of his missing head, harming anyone who stands in his way. One autumn night as Crane leaves a party at the Van Tassel Home, he encounters this Headless Horseman and is never heard from again.
Although the story itself is fictional, it is largely inspired by reality. The final showdown between Ichabod Crane and the Headless Horseman occurs on a bridge near the location where the Horseman is buried. The Old Dutch Burying Ground, the alleged gravesite of the Horseman, still stands in the Village of Sleepy Hollow. The bridge mentioned in the story is referred to as the ""Horseman's Bridge"" and still exists as well although today takes on a more modern appearance. Additionally, the characters themselves are based on real residents of the area. It is believed that the character of Ichabod Crane was based on Jesse Merwin, a schoolteacher in Kinderhook. Although Kinderhook is further north in Columbia County, Washington Irving spent several months in Kinderhook during 1809, well before he published his story in 1820. Similarly, Katrina Van Tassel is thought to have been based Eleanor Van Tassel Brush, with her name coming from Eleanor's aunt Catriena Ecker Van Texel. The gravesites of the Van Tassels, along with the supposed gravesite of the Headless Horseman, are still located within Old Dutch Burying Ground.
(Painting: "The Headless Horseman Pursuing Ichabod Crane" by John Quidor)