Imagination can be a powerful force. 

The story primarily focuses on Ichabod’s rich imagination and how it affects his behavior and guides his actions. He is frequently described as becoming lost in imaginative thoughts about the various foods he will eat, especially when he encounters the abundance of the Van Tassel farm. He decides to pursue Katrina after imagining in detail how prosperous his life would be, but his imagination also blinds him to her disinterest. His obsession with the supernatural is also fueled by his imagination. He spends much of his free time reading Cotton Mather’s “History of New England Witchcraft” and listening to and sharing ghost stories with the townspeople. These influences strengthen and shape his imagination so that he is prone to perceiving the world around him as full of the supernatural. Ichabod has a deep fear of the dark, and he perceives benign encounters, such as the flash of a firefly, or the whistle of the wind, as evidence of supernatural activity. On his ride home from the party, the power of his imagination works him into such a terrified frenzy that he is more willing to believe he is being chased by the Headless Horseman than the idea that Brom is playing a prank on him. The shame of this event forces Ichabod to re-imagine his life, the result of which is a completely new life away from Sleepy Hollow.

Belief in the supernatural helps people explain real fears. 

Sleepy Hollow’s townspeople are steeped in a tradition of belief in the supernatural to help them explain and cope with their trauma and fears. Whether or not they truly believe the town is haunted is irrelevant, because even its skeptical residents adhere to the tradition of passing on stories of hauntings in the area. These shared stories help the community explain actual frightening experiences, many of which are rooted in the American Revolution. The events of the Revolution loom large over this community, which participated in the war and was deeply affected by its horrors. When relaying stories of hauntings, many of the older men in the town lead with stories of their time as soldiers during the war. The tale of the Headless Horseman symbolizes how the war continues to haunt them, as Hessian soldiers fought against the American revolutionaries and were known to be fearsome fighters. Similarly, the story of wailing near the tree where Major André was executed as a spy during the war evokes the same kind of fear in the townspeople. Brom’s joke about having once challenged the horseman to a race breaks the tension and brings levity to a serious moment, highlighting that the town is no longer threatened by war. Brom’s joke reveals that while the war is long gone, its trauma lingers, and ghost stories are a way for the townspeople to cope.

The class structure of postcolonial America is fluid and based on wealth. 

Sleepy Hollow’s class structure is based on wealth rather than on the traditional inheritance structure of the European aristocracy. This was true of all of postcolonial America, where the accumulation or loss of wealth meant a person could rise or fall through the social ranks more fluidly than in a traditional aristocracy. Katrina Van Tassel’s suitors’ efforts to woo her, and especially Ichabod’s, represent this fluidity in action. The Van Tassel family is considered to have a high social status because they own a successful farm. As a result, Ichabod sees marrying Katrina as the key to his social ambitions. And despite his ultimate failure in Sleepy Hollow, he does go on to become financially and professionally successful in Manhattan. Ichabod’s eventual success shows that in postcolonial America, a person can fall to the bottom and still rise to a higher rung on the social ladder.

The narrator also pokes fun at Sleepy Hollow’s parochial society and highlights America’s rural–urban divide. The narrator refers to Katrina as an heiress and to her father as Mynheer Van Tassel and Heer Van Tassel, Dutch honorifics that mean “Sir” and “Lord.” He also humorously refers to the Van Tassel farm as a castle while juxtaposing this with descriptors of the homespun clothing the town farmers consider to be their finest. However, in nearby Manhattan the Van Tassels are considered nothing more than poor farmers. This highlights the disparity between how wealth is viewed within Sleepy Hollow and how the same wealth is viewed in a more prosperous urban center. Though the comparison between Sleepy Hollow wealth and Manhattan wealth highlight America’s rural–urban divide, it also shows that the barriers between the two spheres are minor. In postcolonial America, an impoverished schoolteacher can become prominent member of society in law and government.