Essential Questions: Is change always for the better? In what ways do societies change over time? How do stories help us understand the past?

Project the Theme Anticipation Guide on your whiteboard or share the Google Form version with students. Both are available in your Resources tab. Have students decide whether they agree or disagree with each statement, then discuss. (After reading the story, ask students how they think the characters would respond to the statements in the Theme Anticipation Guide.)

Project the Google Slides version of Vocabulary: Definitions and Practice on your whiteboard. Review the definitions and complete the activity as a class. Highlighted words: amble, bedraggled, bewildered, detestable, grizzled, hackles, impose, mending, peals, saunters. Audio pronunciations of the words and a read-aloud of the definitions are embedded on the slides. Optionally, print the PDF version or share the slideshow link to your LMS and have students preview the words and complete the activity independently before class.

Invite a volunteer to read the As You Read box on page 14 or at the top of the digital story page.

Assign parts and read the play aloud as a class.

Divide students into groups to discuss the following Discussion Questions, which are also located in the Resources tab.

1. In Scene 1, what do you learn about Rip and Cornelia? How are they different? (character) Cornelia is practical and hardworking. She focuses on the important things, like mending the fence, and gets frustrated when Rip doesn’t help with chores. Rip is more of a “dreamer,” and is irresponsible and easily distracted: He helps neighbors, tells stories, and watches the sunset instead of doing the work that is asked of him. He “stops to smell the roses”; Cornelia does not. 

2. What does Cornelia mean when she says, “There’s no time for looking up when there is so much work to be done here on the ground”? (figurative language, character) Answers will vary. Students may say that Cornelia means there’s too much real work to be done to waste time daydreaming. “Looking up” symbolizes Rip’s habit of getting lost in his thoughts or paying attention to the unimportant things. This figurative language helps reinforce how different she is from Rip—she’s focused on reality, while Rip is often distracted by his imagination.

3. What clues help you figure out that Rip has been asleep for many years? How does the playwright reveal this information? (text structure, author’s craft) Clues like Rip’s long white beard, his missing dog, the rusted rifle, the unfamiliar villagers, the inn’s new name, and the fact that people mistake him for a spy all point to the fact that Rip has been asleep for a long time. Instead of explaining this right away, the playwright spreads these clues across multiple scenes, allowing the reader to slowly realize the truth alongside Rip. This gradual reveal builds suspense and helps us experience Rip’s confusion and shock as he begins to understand just how much the world has changed.

4. Consider the characters Peter and Katrina. What is their role in the play? (author’s craft) Peter and Katrina are village elders. Their role in the play is to provide historical context to readers as well as to other characters. For example, they address the audience directly in the prologue and provide information about the time period. In Scene 7, Katrina recognizes Rip, and Peter declares he believes Rip’s story because the mountains are “haunted.” Peter’s word is all the other villagers need in order to accept Rip’s story, because Peter is highly respected in the village.

5. At several points in the play, the mood could be described as “uncanny,” meaning strange in a way that feels mysterious or supernatural. What details from the play help create this mood? (mood, key details) The playwright creates an uncanny mood through details that feel eerie and unexplained. The Odd Fellows whisper Rip’s name from offstage without being seen, which makes them seem ghostly. When Rip meets them, they’re dressed like Dutch explorers from 150 years earlier and don’t speak to him, adding to the mystery. Later, Rip wakes up with a long white beard and an aching body, and doesn’t recognize anyone in the village. These moments make the reader feel uncertain and uneasy, just like Rip does, because they suggest something supernatural is happening, but it’s never fully explained.

6. What does this play tell us about change? (theme, critical thinking) The play shows that change is constant, whether you’re ready for it or not. While Rip is asleep, his whole world changes—his children have grown up, his old friends are gone, his wife has passed, and the country gained independence. These changes happen without him, which shows that time doesn’t stop just because someone avoids responsibility or tries to escape their problems. The play suggests that if you ignore what’s happening around you, you risk missing important moments.

Have students complete the Featured Skill Activity: Narrative Writing. This activity will prepare them to respond to the writing prompt on page 17 in the printed magazine and at the bottom of the digital story page:

Imagine you are a person from a time period you’ve studied in social studies—or from today—who wakes up 20 years later, like Rip Van Winkle. Write a short story or play describing your experience.

Alternatively, have students choose a task from the Choice Board, a menu of culminating tasks. Our Choice Board options include the writing prompt from the magazine, differentiated versions of the writing prompt, and additional creative ways for students to demonstrate their understanding of a story or article.