The great American short story "The Legend of Sleepy Hollow" was written while Washington Irving was living in England, and it was published in England in a volume called The Sketch Book of Geoffrey Crayon, Gent.The Sketch Book was published in installments in the United States beginning in 1819, but the section that included this story was not issued until 1820. Readers on both sides of the Atlantic Ocean thus encountered the story at approximately the same time.

"The Legend of Sleepy Hollow" takes place in Sleepy Hollow, New York, a snug rural valley near Tarrytown in the Catskill Mountains. Constructed from German tales but set in America, it is a classic tale of the conflict between city and country, and between brains and brawn. Ichabod Crane courts Katrina Van Tassel, but is frightened away by his rival, Brom Bones, masquerading as the headless horseman. The story demonstrates the two qualities for which Irving is best known: his humor, and his ability to create vivid descriptive imagery.

Readers immediately took to "The Legend of Sleepy Hollow" and another tale from the Sketch Book, "Rip Van Winkle." Although little formal criticism greeted the arrival of the story specifically, the Sketch Book became wildly popular and widely reviewed both in the United States and in England. It was the first book by an American writer to become popular outside the United States, and helped establish American writing as a serious and respectable literature. In 1864, "The Legend of Sleepy Hollow" was published as a separate illustrated volume for the first time, and there have been dozens of editions since. Today, most of Irving's work has been largely forgotten, but the characters of Ichabod Crane and the Headless Horseman have lived on as part of American folklore.