"The Legend of Sleepy Hollow" is set in the late 18th century, shortly after the Revolutionary War. During this period, the United States was seeking to establish a coherent national identity and the works of Washington Irving—"Sleepy Hollow" included—helped put the young nation on the literary map.
The story takes place in a Dutch settlement called Tarry Town, a small market town on the shore of the Hudson River. Irving based this community on Tarrytown, New York, a village located in present-day Westchester County. A few miles from Tarry Town is Sleepy Hollow, a “sequestered glen” that seems to exist partially outside of time. The hustle and bustle of nearby cities is conspicuously absent from Sleepy Hollow, where the fashions hardly ever change and the residents exist in a state of perpetual repose. Sleepy Hollow’s atmosphere has a “drowsy, dreamy influence” on the area’s inhabitants, who are uniquely prone to superstitions, ghost stories, and supernatural visions. The most popular of these superstitions is the Headless Horseman, who Sleepy Hollow residents believe is the ghost of a Hessian trooper from the Revolutionary War.
Within Sleepy Hollow, the schoolhouse is a key setting that reveals unflattering elements of Ichabod Crane’s personality. Crane uses corporal punishment on his students while simultaneously ingratiating himself with their parents in hopes of getting hot meals and temporary lodging. He is authoritarian to people younger and weaker than he is, but around adults, he is slimy and ingratiating.
Another significant setting is the Van Tassel mansion, home to the wealthy Dutch farmer Baltus Van Tassel and his daughter, Katrina. When Ichabod visits the mansion, he is enraptured by Van Tassel’s abundant fields, well-fed animals, and beautiful grounds. At the sight of so much prosperity, Ichabod’s “devouring mind’s eye” begins to fantasize about claiming these riches for himself by marrying Katrina. This setting reveals Ichabod’s limitless appetite for fine food, beautiful women, and the prestige that accompanies great wealth.
The postscript to "The Legend of Sleepy Hollow" takes place in a new, unexpected setting. Diedrich Knickerbocker, the story’s narrator, relates how he heard the story of Ichabod Crane at “a Corporation meeting of the ancient city of Manhattoes” – Manhattoes refers to the southern tip of Manhattan island during the period of Dutch colonization. In the postscript, Knickerbocker explains that the original storyteller didn’t believe the story himself and only told it to entertain a group of Dutch businessmen. The setting of the Corporation meeting puts "The Legend of Sleepy Hollow" in a social context that casts doubt on Knickerbocker’s claim that his story is “precise and authentic.”
