"Rip van Winkle" is a story that highlights the rapid social changes brought about by the American Revolution. One symbol of that is the quiet inn that turns into the bustling Yankee hotel. Before the revolution, people snoozed outside it, and its portrait of King George III symbolized its sleepy apathy and backwards focus. Afterwards, it becomes a hotel that is a busy, lively spot for political campaigning. The change from a population apathetic under monarchy to one active and engaged under democracy is symbolized by the new portrait of George Washington in the hotel. Possibly nothing characterizes the change more sharply than the portrait of a king replaced by the portrait of a dynamic patriot.
The Dutch bowlers Rip meets in the mysterious valley also symbolize the stasis of pre-Revolutionary times. The story starts out looking backwards, but ends up looking to the future, symbolized by the new Republic.