“The Legend of Sleepy Hollow” was published as part of Washington Irving’s The Sketchbook of Geoffrey Crayon, which came out in 1820. It is probably the most famous story from the collection, and it is considered one of Irving’s most important stories. The Sketchbook of Geoffrey Crayon was extremely well-received in America and was the first work by an American author to be reviewed well in Europe. The collection of stories and essays made Irving’s reputation and established him as a preeminent American author. Most of the sketches concern his observations as an American visiting England, but six, including the two most famous—“Rip Van Winkle” and “The Legend of Sleepy Hollow”—deal with American scenes, including adaptations of German folklore retold with New York as the setting, a romantic defense of Native Americans, and a few other essays.
“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.
One night, after a party at the Van Tassels’ at which Katrina probably rejects Ichabod (she might be in on Brom's plan), Ichabod finds himself joined by a dark figure on a large horse on his ride home. He cannot shake his unwanted companion, and Crane eventually realizes that the horseman has no head. Ichabod does his best to escape, but just when he expects the Headless Horseman to disappear, the ghost instead throws the "head" at him, knocking him off his horse.
The next day, nothing is found of Ichabod but his hat, and next to it lies a smashed pumpkin. Ichabod is never seen in Sleepy Hollow again, and Brom Bones soon after marries Katrina. The townspeople blame Ichabod's disappearance on the headless horseman, but Brom seems to know something more.
The tale thus brings a love story and a ghost story together, but most of all it is a comic tale. The plot appeals to common sentiments, but the story makes fun of communities that are so sleepy that they need ghosts and ghost stories to keep people occupied. It also makes fun of a schoolmaster who is supposed to be one of the smartest people in the town, yet he believes in ghosts and is easily spooked and tricked by a practical joke. The man of letters plays second fiddle to the athletic, strong Brom Bones.