Rip Van Winkle

Use this activity to engage all types of learners, while requiring that they refer to and incorporate details from the text over the course of the activity.

“Rip Van Winkle as an Allegorical Work”

In this activity, students will identify the allegorical elements of “Rip Van Winkle” using evidence from the text to support their response.

Many interpret Irving’s “Rip Van Winkle” as an allegorical text describing the relationship between the American colonies and Great Britain during the Revolutionary War. Consider the different events that sparked The Revolutionary War and identify the elements of Irving’s short story that you believe serve as an allegorical representation of the colonies and Great Britain. Combine the symbols from Irving’s work into a digital presentation. Consider these points as you identify the symbols.

• What is the relationship between Great Britain and the colonies before the Revolutionary War?
• How might the relationship between Dame and Rip Van Winkle parallel the conflict?
• How does Irving explore changing loyalties and the passage of time?
• How does Irving convey the attitudes before and after the Revolutionary War?
• In what ways might the novel’s setting contribute to the allegory?
• How does Romantic literature tie into the attitudes of the story?

Share your presentation with peers and explain your interpretation of the story as an allegory. Use specific passages from the novel to support your response.

Teaching Suggestion: Students may find it beneficial to review the importance of freedom in American Romanticism as well as aspects of the American Revolution prior to completing their allegorical presentation. Consider permitting students to work in small groups on their analysis to generate ideas for how Rip’s story aligns with the Revolutionary War. This Activity connects to the theme of America’s War for Independence and the Meaning of Freedom.

Use these essay questions as writing and critical thinking exercises for all levels of writers, and to build their literary analysis skills by requiring textual references throughout the essay.

Differentiation Suggestion: For English learners or struggling writers, strategies that work well include graphic organizers, sentence frames or starters, group work, or oral responses.

Scaffolded Essay Questions

Student Prompt: Write a short (1-3 paragraph) response using one of the bulleted outlines below. Cite details from the text over the course of your response that serve as examples and support.

1. Rip Van Winkle has become an indelible American character, a folk hero who represents the American identity of the late 18th century.

• In what way is Rip Van Winkle representative of American culture and values before or after the Revolutionary War? (topic sentence)
• Describe ways in which Irving creates a folk hero in the figure of Rip Van Winkle.
• In your concluding sentence or sentences, explain why Irving chose to highlight Rip Van Winkle’s American attributes.  

2. Rip Van Winkle is illustrative of American Romantic ideals.

• How is Rip Van Winkle a Romantic hero? (topic sentence)
• Describe three character attributes of Rip Van Winkle that align with an American Romantic hero.
• In your concluding sentence or sentences, compare Irving’s presentation of Romanticism with that of other American Romantics.

Full Essay Assignments

Student Prompt: Write a structured and well-developed essay. Include a thesis statement, at least three main points supported by textual details, and a conclusion.

1. Rip is described as having positive and negative attributes. Consider whether Rip should be considered an admirable character. Evaluate his character in two or three paragraphs, considering both his flaws and positive attributes and the societal expectations for men at the time the story was written. Support your answer using evidence from the story.

2. Rip Van Winkle awakens after 20 years to discover that the community he once knew has been changed forever by the Revolutionary War. Explore Irving’s depiction of the conflicting forces of tradition and revolution. Incorporate multiple details into a brief paragraph to describe Irving’s message about the changes the nation underwent during the American Revolution. Use specific quotes from the story to support your response.

Multiple Choice and Long Answer Questions create ideal opportunities for whole-text review, exams, or summative assessments.

Multiple Choice

1. What statement best serves as a moral for Rip Van Winkle’s story?

A) Hard work produces peace.

B) Laziness is a waste of time.

C) Change is important for survival.

D) Freedom is essential for a happy life.

2. What is the purpose of Irving’s depiction of Diedrich Knickerbocker, a fictional historian, in relating the tale to his audience?

A) It is used as a humorous prelude, adding to the overall tone of the story.

B) It provides first-hand accounts so the reader can determine its trustworthiness.

C) It lends credence to the believability of Irving’s short story.

D) It mocks the scholarly class of the American Colonies, who were strongly pro-Revolution.  

3. Which of the following best classifies Rip Van Winkle’s character type?   

A) Dynamic

B) Flat

C) Round

D) Static

4. What does the narrator claim to be the only tool that becomes sharper with constant use?

A) Knives

B) The tongue

C) A pickax

D) The mind

5. What does the Inn/Union Hotel symbolize in the short story?

A) The changes in the American landscape from patriotism to laziness.

B) The passing of Rip’s wife and all that he loved in his village.

C) The passage of time and changes that occur within a lifetime.

D) The changes in Rip Van Winkle’s character from lazy to productive.

6. In the story, which individual functions as both a historical figure and a mythological founder of the American identity?

A) Henrick Hudson

B) Diedrich Knickerbocker

C) Rip Van Winkle

D) King George III

7. Which of the following best identifies elements of Romanticism in Irving’s story?

A) The narrator’s emphasis of the importance of familial ties and personal responsibility.

B) Rip’s acceptance of progressive social changes he observes in the village. 

C) The narrator’s description of the Catskill Mountains’ majestic and mysterious beauty.

D) The stern, judgmental narrative voice that criticizes Rip’s character flaws.

8. What relationship does Irving satirize in his description of the relationship between Rip and Dame Van Winkle?  

A) The relationship between the American people and the Dutch colonists.

B) The relationship between the American Colonies and King George III.

C) The relationship between the colony of New York and the Federal government.

D) The relationship lazy people have with the rest of society.

9. Which phrase best describes the villagers’ response to Rip Van Winkle’s return from the mountains?

A) Suspicious and unfriendly

B) Disinterested and dismissive

C) Surprised and grateful

D) Curious and welcoming

10. Which statement best depicts the changes made to American culture after the American Revolution?

A) America became more concerned with freedom and less concerned with commerce.

B) America changed temporarily but returned to the tranquil culture it was before the war.

C) American culture became busier because of an interest in politics and commerce.

D) There were few changes made to the American culture during the short passage of 20 years.

Long Answer

Compose a response of 2-3 sentences, incorporating textual details to support your response.

1. In what way does the short story portray typical elements of American Romanticism?

2. Though Rip is described as lazy in the narrative, many of the villagers tend to side with Rip as opposed to his wife in their troubles. Why do the villagers prefer Rip over his wife? Whom do you believe to be responsible for the financial ruin of the Van Winkle family? Support your response using evidence from the text.