Numerous critics have explored Irving's knowledge of seventeenth-century Dutch or Flemish art. Rip himself recalls an "old Flemish painting" when he observes the bowlers in their peculiar attire. Locate paintings depicting rural life by artists like Adriaen Brouwer, Willem Buytewech, Jan Steen, Adriaen van Ostade, Esaias van de Velde, or other Dutch genre painters. Does Rip’s impression that the strangers form a "melancholy party of pleasure" resonate with the scenes shown in these artworks?

Compile a list of significant American publications from the early nineteenth century. How do Irving's stories stand out? What similarities do they share with other contemporary writings?

During Rip Van Winkle's twenty-year sleep, he misses the American Revolution and wakes up in an independent nation. Investigate the changes in Rip's village before and after his prolonged sleep, as well as in colonies like New York just before and after the Revolution. How significantly did this major political shift impact daily life?

Map out the journeys of Henry Hudson across North America. Where did he travel, and when?

Find a collection of Native American folk tales, especially those from the Native tribes of upper New York. How do these tales compare to folk tales from other regions around the globe? What common values are shared among the different cultures? Which values are unique?