"The Legend of Sleepy Hollow" takes place at a time when the United States had only recently achieved its independence. Washington Irving's stories often describe a setting that exists half in the old world and half in the new. There is a sense that the past has been shaken off but that there are remnants of it that persist in the minds of the people. In Irving's "Rip Van Winkle," the title character himself, a relic of the past awakened into the new world, symbolizes this division.

In "Sleepy Hollow," the past is represented by the legend itself, a supposed ghost of a Hessian soldier from the War of Independence. The Revolution is over and the British and their Hessian allies have been defeated, but this figure haunts the imagination of the residents of Tarry Town. The Hollow is a magical place that holds its power over people's minds in spite of the Enlightenment and the new, soon-to-be mechanized world that is emerging. So the elementary conflict is between past and present and...

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