Set in the small secluded valley of Sleepy Hollow, Irving’s short speculative story follows the rivalry between Ichabod Crane and Brom Van Brunt for Katrina Van Tassel’s hand in marriage. Mostly inhabited by descendants from Dutch settlers, the residents are known for their belief in superstitions and the supernatural, and have many stories to suffice their colorful imaginations. The story begins when the scrawny schoolmaster Ichabod Crane from Connecticut moves to Sleepy Hollow for a teaching job and rotates living with the families of his students. This type of living arrangement allows him to grow familiar with the stories circling the strange town. The most popular phenomena being that of the Headless Horseman, supposedly ghost of a Hessian soldier who lost his head during a battle in the American Revolutionary War.

As Ichabod adjusts to his new home town, a visit to the rich farm of Baltus Van Tassel inspires him to win the hand of his only daughter Katrina. However, Katrina’s beauty and wealth have also attracted the attention of other bachelors in town including the exuberant Brom Van Brunt, or locally known as Brom Bones. Well in the habit of intimidating and scaring off Katrina’s suitors, mostly through physical confrontations, Brom instead turns to pranks as his main method of persuading Ichabod to give up on his love quest. A story torn between logic and superstition, the characters must determine what is real and what is not, or fall victim to local myths determining their fate.

Other than being an intriguing story of greed, superstition and the supernatural, Irving also uses his main character Ichabod as a means of satire, mocking the seemingly refined culture of city dwellers. It is no coincidence that the educated Ichabod trades big city life for the small Sleepy Hollow, and is victim to the many pranks played on him. The Legend of Sleepy Hollow is one of the earliest samples of American fiction which has remained a classic and favorite among its readers.