33 pages 1 hour read

Rip Van Winkle

Fiction | Short Story | Adult | Published in 1819

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During Reading

Reading Questions & Paired Texts

Reading Check and Short Answer Questions on key points are designed for guided reading assignments, in-class review, formative assessment, quizzes, and more.

Reading Check

1. Where does the story of Rip Van Winkle take place?

2. What is Rip described as having an aversion to?

3. Who, in Rip’s family, does he consider to be as “henpecked” as himself?

4. What is the man Rip meets in the woods carrying?

5. How long has Rip been missing from his village after he awakens on the mountain?

Short Answer

Answer each question in at least 1 complete sentence. Incorporate details from the text to support your response.

1. What are Rip Van Winkle’s strengths and vices, and how do they impact his relationship with his neighbors?

2. Describe Rip Van Winkle’s relationship with his wife. How does their relationship impact the function of their home?

3. What does Rip identify as being unusual when he wakes up from his sleep? What does he suspect to be the cause of these unusual happenings, and at which moment does he suspect something nefarious has happened to him?

4. Compare the mannerisms of Rip’s former village to the newer, more modern village. How have the attitudes, identity, and culture of the village shifted?

Recommended Next Reads 

The Legend of Sleepy Hollow” by Washington Irving

  • This short story is about an awkward schoolteacher who encounters a ghostly figure in a small port town.  
  • Shared themes include Myth in the Old and New World.
  • Shared topics include folklore, the Revolutionary War, and lighthearted comedy.
  • “The Legend of Sleepy Hollow” on SuperSummary

The Monkey’s Paw” by W.W. Jacobs

  • This short story is about a family who acquires a magical monkey paw that grants its owner three wishes, but not without consequences.
  • Shared themes include Myth in the Old and New World.
  • Shared topics include magical realism, choices and consequences, and the evils of magic.
  • “The Monkey’s Paw” on SuperSummary

Reading Questions Answer Key

Reading Check

1. The Kaatskill (Catskill) Mountains (Paragraph 4)

2. Profitable labor (Paragraph 8)

3. Wolf (Paragraph 12)

4. A keg (Paragraph 20)

5. 20 years (Paragraph 51)

Short Answer

1. Rip is described as a kind, good-natured, meek, simple, and obedient husband. Rip’s vice is described as an “aversion to profitable labor” (Paragraph 8) and he has some difficulty completing work on his farm. Rip has gained “universal popularity” in his village as the women blame Dame Van Winkle, the men identify with Rip’s plight, and Rip often plays with the children, gaining their favor. (Paragraphs 6-9)

2. Dame Van Winkle is said to be a “termagant” wife and Rip is described as “hen-pecked.” Their relationship is therefore tumultuous. Rip often avoids his home because of Dame Van Winkle’s treatment of him. For example, Rip can often be found at the inn with the village gossips or wandering the hills as a form of escape from his wife. Rip’s avoidance of the home has consequences for his children who are “ragged and wild” (Paragraph 10), and his farm is “the worst-conditioned farm in the neighborhood.” (Paragraph 9) These passages indicate that Rip is neglectful in caring for his family and his livelihood. (Paragraphs 6-13)

3. Rip, upon awakening, notices he is very stiff, Wolf is missing, and his gun is rusted. He initially believes the men he had seen the night before pranked him during his sleep. He first becomes aware of what may have happened when he notices his beard has grown significantly. Additionally, Rip sees that his home is now in disrepair, Wolf has grown old and mean, and the inn he used to frequent is now called “The Union Hotel.” (Paragraphs 26-34)

4. Formerly, Rip’s quiet village was tranquil and lazy in its approach to politics and life. Rip and his friends spent many hours in the taverns talking and gossiping. Additionally, the town was loyal to King George and had his portrait hanging above the quiet inn. Twenty years later, upon awakening, Rip notices the busyness, suspicions, and argumentative nature of the villagers. Their loyalty is now to George Washington. (Paragraphs 33-36)

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