As the two protagonists battle wits, a subplot becomes evident: choices must be made between the old order and the new order. The sturdy Brom Bones, with his practical, quaint Dutch upbringing, is a cog in a hole (or the whole, that is the village). Brom fits Tarry Town, and his rowdy mischievous nature functions as a pleasant diversion in the quiet little village. Brom represents the virtues of the old, tried-and-true order of the original settlers of the Sleepy Hollow area. Should Katrina choose Brom, she knows exactly what she will be getting. Not much will change in Katrina's life, one assumes, should she decide to marry the local fellow. Brom would be likely to assume some lesser role in the operations of his father-in-law's farm, which means that the happy couple will remain under the watchful eye of Katrina's doting father. Perhaps, over time, Brom will win over his father-in-law, if only because Brom brings a strong and willing back -- coupled with an irresistible good nature -- to the stoic existence of those who make their living from the soil.

Crane, on the other hand, represents a new order -- or at least he approximates what a new order could be. What is of particular interest is that Crane is so myopic: as a learned man, it is fair to expect him to be sophisticated enough to not be so very superstitious. Because of his slight build, he can be forgiven his timidity -- which is in high contrast to Brom's temerity. Crane's slight build may also be the result of an inadequate diet. As...

Immigrants -- newcomers of any sort -- like Crane, may have few resources at their disposal. It is the nature of an immigrant to be attracted to a land and a people because of the promise of a better life. Faulting Crane for his ambition is problematic, when it is the essence of the American dream, of Manifest Destiny. Although the term Manifest Destiny would not be known for roughly another hundred plus years -- the concept applies here. Crane was a pilgrim, and his motives were not as pure as they might have been.
After the disappearance or death of Ichabod Crane -- the reader can never be quite sure of the outcome -- Tarry Town was likely not much changed, as Ichabod did not cast a wide shadow. But the lives of Brom, Katrina, and Baltus van Tassel were transformed. The literary or figurative death of Crane opened the way to new relationships and new lives in this small circle of Dutch settlers.