In the Dutch valleys like Sleepy Hollow, there is a central conflict between life in the towns and cities that are becoming increasingly industrialized and the more traditional life on the farm. Sleepy Hollow is not against accepting new neighbors. Even still, the storied history of its Dutch inhabitants leaves quite a legacy.

As a newcomer to Sleepy Hollow, Ichabod attempts to reconcile this conflict. His role as a schoolmaster could certainly be seen as representing the city, or modernity. He is conscious of his role in the town. Though many of the members of the community who live in the rural area do not send their children to Ichabod’s school, viewing it as a financial burden, Ichabod still seeks to leave a good impression on them. He finds different ways to be both “agreeable and useful.” He helps them with their children or with light farm work, thus establishing himself in the country as well as the town.

The conflict between city and country is personified in Ichabod and Brom Bones, respectively. Ichabod is fascinated by the countryside and how he could benefit from it. Brom Bones, on the other hand, is a countryman who understands the lay of the land. Their skill sets are quite different. Brom is strong and accustomed to physical labor. Ichabod has musical talents and is educated, representing the outsider background he comes from. Both seek to marry Katrina, but Brom is ultimately the winner in this endeavor. The narrator implies that Sleepy Hollow is a dreamy place untouched by time—even when Ichabod disappears, the bounty of the area’s farmland and history lives on.