"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.
One of the most mysterious persons in the story is a man who carries a keg up a mountain and asks Rip to help. Rip notices that he is dressed as a 17th century Dutchman. When they arrive in a meadow, one of the men is addressed as "Commander". It is after that scene that Rip drinks some of the liquor and falls asleep for 20 years. So, who were those people and who was the commander? After Rip awakens, someone tells him that the ghost of Henry Hudson, who discovered the New York area where the story takes place, comes back every 20 years to haunt the place. This implies that the men were part of Hudson's crew and the commander was the ghost of Hudson, a symbol of adventure and discovery. Rip certainly has an adventure and discovers much about the future after he wakes up.