Rip’s emancipation from his husbandly and fatherly duties metaphorically reenacts the American War of Independence (1775-1783). With lighthearted satire, Irving draws parallels between the tyranny of the Crown and the tyranny of day-to-day responsibilities. Rip owes work to Dame Van Winkle like the American colonies owed fealty to Great Britain until finally, both Rip and the colonies escape from under the thumb of their oppressors.

Still, when Dame Van Winkle is long dead, Rip nostalgically admits that she “kept a good house”—a sentiment that gestures to the fact that by the 18th century the relationship between American and Britain was closer than ever: trade flourished, and a common culture prized commerce and the concept of liberty.  

With Dame Van Winkle gone, Rip is free to once again become the town gossip and storyteller—that is, to resume his old way of life. His house is a mess, the portrait hanging in the tavern is different, the people are busier, but other than that, not much has changed. Though the removal of Great Britain has changed life at the top, everyday Americans need the connection to the past that Rip provides.