1. Who are the “Strange men” that Rip encounters in the hollow?
2. Is it helpful to know that the story is based in a German fairy tale? Why or why not?
3. Is Rip’s long sleep a reward (perhaps for helping the man playing ninepins) or a punishment (for being la generally lazy guy?)
4. What is the portrayal of women in the story, including that of Rip’s wife Dame Van Winkle? Can you think of a more contemporary story where a “nagging” wife is so central to a story’s plot?
5. Are there other characteristics in literature that compare to Rip van Winkle?
6. Is Rip van Winkle consistent in his actions? Is he a fully-developed character?
7. Discuss some of the symbols in Rip van Winkle.
8. How essential is the setting to the story? Could the story have taken place anywhere else? What if the story had been set before and after the Civil War, or the War of 1812?
9. How realistic is Irving’s depiction of the Catskills? Why did he choose to set the story there?
10. How does time figure into the story? Why was rip’s slumber 20 years longs, and not 10 years or 30 years.
