Instead, people are valued for their merits, such as their book learning or their ability in teaching, activities requiring strength, or singing (Hoffman 7). In the period in which Irving based his story, few rural people were educated enough to teach. Therefore teachers had to come from the city. The entry of Ichabod Crane represents the intrusion of the city. D. Victor explains this as "The recalcitrant attitude towards change and education was evident in the perception of schoolmasters as "mere drones" or the costs of schooling as "a grievous burden"" (Victor 1).
The description of Ichabod as tall, awkward and erudite made the pedagogue seem wimpy in the rural area (Hoffman 9). The fact that he associated with the womenfolk more often strengthened this view. Irving wrote the characters based on the stereotypes associated with the Dutch and Yankees, of the time, in this story. The Dutch (Brom) were thought to be foolish and brawny while the Yankee (Ichabod) were thought to be sophisticated, pompous and vain. The use of these stereotypes improved the split between city and country in this story (Victor 2). "The Legend of Sleepy Hollow" also is redeemed from derivativeness by its ties to specific historical backgrounds and to contemporary social and political issues. The story is founded in regional history, most prominently building on the fact that New York was initially a Dutch colony and retained Dutch influences through the nineteenth century. Irving utilizes the "ancient" and "peculiar" Dutch (p. 272) to add apparent depth to American history and to stand as a sort of American folk. Irving also tethers the tale to local events of the Revolutionary War, setting it within what was the "neutral ground"-a segment of the Hudson Valley caught between the British and American armies for most of the war and plagued with violent infighting among residents.