Tarry Town, also known as Greensburgh, lies between the Hudson and Tappan Zee rivers, and it is a small market town. Near this town is a very quiet glen named Sleepy Hollow. In this glen, the land and its people all seem to exhibit a quality of dreamy drowsiness. Diedrich Knickerbocker, whose story this is, is convinced that this quality has been caused by some kind of spell or curse. Because of its relative isolation for a fair amount of time longer, Sleepy Hollow has more than its share of legends, superstitions, and strange occurrences.
The town’s most dominant spirit is that of a headless man riding on horseback, believed by many to be the ghost of a Hessian soldier from the Revolutionary War, who is frequently seen rushing quickly through the village, often near the church. It is thought that he is rushing in search of his head, and he is known throughout the region as The Headless Horseman of Sleepy Hollow.
Ichabod Crane, originally from Connecticut, is the schoolmaster of Sleepy Hollow. His school house is designed so that any thief could break in easily but would find it difficult to get back out. He believes in disciplining his students with the rod, although he is careful to use it only against those who can bear it, and he treats the weaker students much more gently.
The students do not hate him, and this benefits Ichabod, for by custom he relies on the hospitality of his students’ families to give him room and board, each for a week at a time, since his pay is very low. He has few possessions. To alleviate his burden on the families, Ichabod does his best to make himself useful around the farm and to be on good behavior. He is also the singing master of Sleepy Hollow, for which he makes some extra money, and the local women like his skills, so he gets by quite well.
Ichabod’s status as the schoolmaster, being second in learning only to the parson, gives him much of his importance in the female circles of Sleepy Hollow. His traveling lifestyle gives him greater access to gossip than most have, which adds to the welcome that he receives in most of the farmhouses. Ichabod is fascinated by Cotton Mather’s History of New England Witchcraft, and he is a firm believer in it and in the supernatural generally. Indeed, he often spends all afternoon reading this history before heading home for the week, and he scares himself so badly that he must sing psalms while walking to maintain his composure. He also enjoys listening to the housewives tell their ghost stories, especially those involving the Headless Horseman, and he scares the women with his stories of witchcraft in return.
Ichabod Crane is an anti-hero in that he is the tale’s protagonist and has some good qualities, but his serious character flaws make him not admirable—and these flaws will doom him. He is a schoolmaster, but he does not seem particularly interested in his students, and he is only well-educated relative to the others in the town, having finished a few books. The only one he seems to focus on is Cotton Mather’s History of New England Witchcraft. He is obsessed with the supernatural apart from religious faith, despite his learning. This in itself is not enough to make him foolish, but he fails to realize that he is the agent of his own undoing in that he makes himself scared just to walk home at night.
In addition, this opening section makes clear that, although Ichabod is popular with the ladies of Sleepy Hollow for his gossip and his relatively advanced education, he would not be much of a catch as a husband—he can barely support himself, is homeless, and seems to have a mistaken idea of his own worth. The narrator, Diedrich Knickerbocker, uses irony and sarcasm when giving Ichabod accolades for what skills he has, such as his singing voice. Ichabod Crane also has a “speaking name” in that he looks like a crane, a kind of bird. He is an outsider compared to the residents of the town, which has gone on its way with its own traditions for a relatively long time without him.
The emphasis on Sleepy Hollow’s unusual amount of ghost stories and legends is interesting, for “The Legend of Sleepy Hollow” is one of the few sketches in The Sketchbook of Geoffrey Crayon that is not set in Europe. The dichotomy that Crayon makes throughout The Sketchbook is between storied Europe and young, unstoried America. But Sleepy Hollow is filled with people who are descended from its original settlers; it is, therefore, full of stories and legends, although still relatively young compared to European villages. Sleepy Hollow has a quality that is rare in early America—its inhabitants have all lived there for generations, instead of moving around frequently. This allows histories and legends to be built and passed on in a way that would otherwise be impossible.
Irving himself is doing his part to create a distinctly American literary tradition, distinguishing American ways from European ones and focusing on distinct American traits. These include unprecedented levels of liberty and ease of movement and migration, vast available resources, and little emphasis on class hierarchy. These characteristics are present in and around Sleepy Hollow, so Sleepy Hollow’s legends and folklore can have a particularly American flavor. Knickerbocker seems quite pleased with their existence.
Indeed, stories are essential in “The Legend of Sleepy Hollow.” They add excitement to Ichabod’s otherwise fairly mundane life and the similarly mundane lives of the townspeople. They serve as his currency for treats from the farmer’s wives, providing for a welcome stay in their homes. Ichabod’s work to educate the children of the town seems to be valued less than his enjoyment of supernatural stories, his energy in sharing them, and the ways that his own experience will become another set of stories for the community.