One of the great works of American folklore, "The Legend of Sleepy Hollow" is a classic tale of the conflicts of City versus Country and brains vs. brawns. Another predominant theme is that of Imagination.
City versus Country
With the new frontier of America, it was expected that the view of the city as corrupt and ugly against the beauty of the vast expanses of countryside would predominate.
Ichabod Crane, a native of Conneticut "tarried" in Sleepy Hollow in order to be a school teacher for the children. With his narrow shoulders, long arms and legs and spindle neck on which a small head sits, Crane is in sharp contrast to the robust woodsmen of the area. His rival for the love of Katrina Van Tassel is Brom Bones, the "hero of the country round," who is famous for his skill in horsemanship and his feats of strength. It is this skill that the "redoubtable" Brom uses to foil Crane's clever attempts to ingratiate himself with the women of the county, especially Katrina Van Tassel whose bountiful home entices him with thoughts of ducks, turkeys, sausages, and pies.
Very impressionable, Ichabod is "esteemed by the women as a man of great erudition," because he is a teacher and "master" of Cotton Mather's History of New England Witchcraft, but he firmly believes it. So, as he spends long winter evenings with the Dutch matrons, Ichabod feeds his mind with all the old wives' tales. However, his failure to distinguish wives' tales from reality is what leads Crane to fall under the spell of the "drowsy, dreamy" valley. As a consequence of his gullibility, he becomes terrified when he encounters what he believes is really the Headless Horseman, and he falls prey to Brom Bones. Ironically, Ichabod himself becomes part of the community imagination:
The old country wives...maintain to this day that Ichabod was spirited away by supernatural means.
The theme of Imagination is certainly the theme that lends Irving's charming tale its folklorish color and humor as the vision of Ichabod "clasping old Gunpowder round the neck" as the saddle falls off and the black steed and "goblin rider passed by like a whirlwind" lingers long in American culture.