“The Legend of Sleepy Hollow,” thought to have a source in a German folktale, tells the story of Ichabod Crane , a greedy and naïve schoolmaster from Connecticut who tries to win the hand of the flirtatious and very wealthy Katrina Van Tassel . Brom Bones, a neighborhood hero, is also in love with Katrina, and he has a tendency to play pranks on others, which will come to haunt Ichabod soon enough. Ichabod is especially fascinated by ghost stories and witches, and Sleepy Hollow is known for its supernatural activity--especially its infamous ghost, the Headless Horseman.
The story was the longest one published as part of The Sketch Book of Geoffrey Crayon, Gent. (commonly referred to as The Sketch Book ), which Irving issued serially throughout 1819 and 1820, using the pseudonym "Geoffrey Crayon".  Alongside " Rip Van Winkle ", "The Legend of Sleepy Hollow" is one of Irving's most anthologized, studied, and adapted sketches. Both stories are often paired together in books and other representations, and both are included in surveys of early American literature and Romanticism .  Irving's depictions of regional culture and his themes of progress versus tradition, supernatural intervention in the commonplace, and the plight of the individual outsider in an homogeneous community permeate both stories and helped to develop a unique sense of American cultural and existential selfhood during the early nineteenth century.