The Romantic Period: “Rip Van Winkle” was published in 1819, just as the Romantic movement was gaining traction in the United States, having already spread from Germany to England. Romanticism in literature emphasizes the powers of the imagination. Many Romantic works also explore the natural world and the past. Each of these features can be found in “Rip Van Winkle.” The story’s layered narration and Rip’s strange slumber bear the imprint of the imaginary. The wild, unexplored landscape of the Hudson Valley and its Dutch colonial heritage also figure prominently.

• For discussion: How is the setting described throughout the story? What emotions do these descriptions evoke?
• For discussion: What seems to be Rip’s relationship with nature? How does it affect him? Have you ever been affected by nature in a similar way?
• For discussion: How are the strange men in the Catskills described? Who are they? What role do they play in the story?
• For discussion: How are the events of the narrative filtered through one or more layers of imagination? What role might imagination play in shaping the telling of those events?

The Frame Story and the Folktale: “Rip Van Winkle” is a frame story, meaning that it contains another story within its narrative. In this case, the frame consists of Geoffrey Crayon’s notes about the fictional historian Diedrich Knickerbocker. Knickerbocker’s account of Rip Van Winkle forms the story within the frame. “Rip Van Winkle” is also contextualized as a folktale, and elements such as Knickerbocker’s research methods and Peter Vanderdonk’s stories of Hudson nod to the development of folktales through the oral tradition.

• For discussion: What does the epigraph at the beginning of the story mean? What is its effect on the rest of the story?
• For discussion: Who is Diedrich Knickerbocker, and why is he important? How does Geoffrey Crayon describe him? How does Crayon’s description of Knickerbocker affect your reading of “Rip Van Winkle”?
• For discussion: What do Diedrich Knickerbocker’s notes at the end of “Rip Van Winkle” say? What do they add to the story?
• For discussion: What points do you think Rip might have varied on as he first began to tell his story? Why? How might another character, such as Dame Van Winkle, have told his story instead?
• For discussion: Who would you call the narrator of Rip’s story: Crayon, Knickerbocker, or Rip himself? In what ways does that narrator work to make the story sound true? In what ways does the story sound fictitious?

Tradition Versus Modernity: The main source of tension in Rip’s life can be attributed to his aversion to profitable labor. When he awakens twenty years later, he finds that his small town has grown and become more politically engaged. Rip doesn’t bother himself with the town’s energetic pace and interest in politics. Instead, Rip continues his life of idleness and storytelling. In this, Rip symbolizes the secluded and simple nature of his town as it was in the past. Now, his village has changed, but Rip’s support by its younger citizens shows how tradition and modernity are connected. 

• For discussion: How was Rip Van Winkle treated by his village in the beginning of the story? How is he treated by the village when he initially returns from his twenty-year sleep? How is he treated after he has reestablished himself in the community?
• For discussion: What particular changes does Rip notice about his village after he wakes up? What does he eventually discover to be unchanged?
• For discussion: How do Rip’s personality and mannerisms contrast with those of the new villagers? Given this contrast, what do you think Rip represents within the story?
• For discussion: Some of the changes Rip encounters upon his return are more surface-level than others, such as the paint that has changed the portrait of George III to one of General Washington. How much has Rip’s village changed on a deeper level? Are the personalities and interests of its people truly different from when he left? How so? What themes might be revealed through these different levels of change?

Additional Discussion Questions:

• Is Rip Van Winkle an unreliable narrator? Is Diedrich Knickerbocker an unreliable narrator? Is Geoffrey Crayon an unreliable narrator? What is the effect of having three narrators of questionable reliability?
• Why do you think Crayon uses Knickerbocker’s notes to tell the story of Rip Van Winkle? Would the story have seemed more or less credible without the inclusion of Knickerbocker?

Tricky Issues to Address

The Story Engages Deeply with Historical Material: In “Rip Van Winkle,” Washington Irving explores the impact of the American Revolution. When Rip falls asleep, the American colonies are under the sovereignty of King George III. When he wakes, twenty years have passed, bringing the Revolutionary War and the birth of the United States. Readers of Irving’s story are well served by understanding these historical undercurrents.

• What to do: Discuss the historical backdrop of “Rip Van Winkle” with your students before assigning the story. Briefly review the United States’s transition from British colonies to independent nation.

Students Will Know the Story: The plot of “Rip Van Winkle” has become a fundamental piece of the American folkloric tradition, and many students will likely have encountered it before. A feeling of familiarity may lead students to disregard the story’s subtlety and literary value.

• What to do: Discuss the specifics of the story. Students may know that Rip falls asleep for a long time, but they may not know what happens in the world while he sleeps or the range of themes his story engages with.

The Story Perpetuates Sexist Stereotypes: Dame Van Winkle embodies the stereotype of the “termagant,” or overbearing and nagging woman. Conversely, Rip embodies the stereotype of the lazy, ineffectual husband. These stereotypes have their roots in traditions of stock comedy, and can be found in numerous literary works, including Irving’s other fictions.

• What to do: Draw students’ attention to the outmoded stereotypes so that they can engage with them critically, rather than reading their presence as a given. Such critical engagement ensures a keener reading of the story and curtails further perpetuation of the stereotypes. To bolster such a critical reading, consider drawing on the second alternate teaching approach in this guide.
• What to do: If students show interest in the topic, discuss with them the function of stereotype in such genres as stock comedy and folklore. 

Alternative Approaches to Teaching "Rip Van Winkle"

While the main ideas, characters, themes, and discussion questions above are typically the focal points of units involving teaching “Rip Van Winkle,” the following suggestions represent alternative readings that may enrich your students’ experience and understanding of the story.

Focus on the supernatural aspects of the story. “Rip Van Winkle” includes several supernatural and mysterious aspects. It also shares plot elements with fairy tales. Ask students to analyze how the fantastical parts of the story contribute to the story’s fabular quality. 

Focus on Rip and his wife’s marriage. Point out to the students that Irving uses exaggerated tropes of an overbearing wife and a lazy husband. Ask students to find stereotypes about both Rip and Dame Van Winkle within the text. Ask students what points of satire can be found through the characters and their interactions with one another. In particular, encourage students to consider Rip and his wife’s marriage as a satirical analogy for the American colonies’ relationship to the British Empire in the years before the American Revolution.