One of the themes of American Literature and American folklore is the differences and comparisons of city people and country people. Ichabod Crane is a city man, educated , intelligent, gentile, but not the outdoor type. Once he falls in love with Katrina Van Tassel, he is in direct competition for her affection with Brom Bones who is a country man, a strong, skilled horseman, with a sense of humor.
When the headless horseman is seen by Ichabod Crane, it is done to prove to him that he does not belong in the country. He is weak, frightened and gullible.
The story behind the headless horseman about a Hessian soldier who lost his head during the Revolutionary War, and every night he rides his horse looking for his head, has made a distinct impression on Crane, who is interested in spirits and magic.
Brom Bones shows Crane that he is less of a man than he is, because he falls for the tale of the headless horseman and is scared out of his mind. He does not have what it takes to live in the country.
"Suddenly, he sees a large shadowy figure on the road ahead. It appears to be a headless man riding a horse, and Crane can just make out the shape of a head resting on the pommel of the saddle. Terrified, he races away, chased by the headless horseman. He is unable to escape. The last thing he remembers is the sight of the rider about to throw the head at him; struck by the flying object, he is knocked unconscious to the ground."