The central conflict of "Rip Van Winkle" involves competing visions of American society following the Revolution. In the story, Washington Irving reveals an America falling short of its romanticized vision. He presents this symbolically through the journey of his title character, Rip.
For those who had supported and fought the Revolution, the post-war period seemed one of unrestrained possibilities. Indeed, some went as far as to characterize it as a golden age. Such attitudes regarding
America as Utopian were not altogether new, however, with some going back as far as the Puritan notion of the New World being a "city on a hill," there for all to study, admire, and emulate.
Irving, however, saw the post-war period as all but Utopian. Instead he saw American society as driven by avarice and political ambitions. As put by Lehigh University Professor Edward J. Gallagher, the story “really bemoans the fact that the Revolution marked the drastic change in America from bucolic paradise to commercial and political Babel.”
As such, Irving envisioned a society that left too many people behind, an idea embodied in the sleeping Rip, who awakens only to find himself incapable of adjusting to the changes he observes all around him. Instead Rip feels out of place and disoriented, yearning for a simpler past. Hence, the critical conflict in the story is as much a criticism of the post-Revolutionary period as it is a nostalgic longing for a bygone era.