Rip Van Winkle

Use these questions or activities to help gauge students’ familiarity with and spark their interest in the context of the work, giving them an entry point into the text itself.

Short Answer

1. What are the reasons behind the rebellion of the American colonies during the Revolutionary War? What changes may have occurred in American culture after the war?

Teaching Suggestion: Rip Van Winkle awakens after a 20-year sleep to discover that American culture has shifted from tranquil to bustling. These changes are part of the aftermath of the Revolutionary War. Students may find it beneficial to understand the motivations behind the American Revolution to consider the allegorical nature of the short story as Rip’s relationship with his wife represents the relationship between America and Great Britain. Consider discussing the reasons behind the rebellion of the American colonies then explore the links to further investigate the cultural changes made because of the American Revolution. This activity connects to the theme of Freedom.

• This 10-minute video explores the reasons behind the American Revolutionary War.
• This article describes the instability and changes in American culture following the Revolutionary War.

2. What are the elements of American Romanticism? How might Romanticism have had an impact on American culture?

Teaching Suggestion:  Rip Van Winkle’s attitudes and perspectives reflect those of American Romanticism. American Romanticism is an important concept to explore for the short story as it will provide the reader with greater context for Irving’s glorification of Rip’s freedom. It may be beneficial for students to first read the articles before answering the questions. Consider creating an anchor chart of Romantic elements for students to refer to as they read the story.

• This article describes the elements of American Romanticism.
• This article explores the various periods of American literature, including American Romanticism, and provides examples from this literary movement in the United States.

Personal Connection Prompt

This prompt can be used for in-class discussion, exploratory free-writing, or reflection homework before reading the story.

Consider the technological and ideological changes that have been made in your lifetime or in past generations. Do you believe the world to be rapidly changing or changing slowly? What changes in technology or culture can you identify in recent history?

Teaching Suggestion: Rip Van Winkle drinks from a keg during a mysterious encounter in the Catskill Mountains and awakens 20 years later to vast changes to the American landscape. Consider discussing technological or ideological changes that have happened during the students’ lifetimes and speculate as to the changes that may be made in the next 20 years.

Differentiation Suggestion: Students who require an additional challenge may find it beneficial to create a timeline charting social and technological changes that have occurred in the last 20 years. Consider allowing the students to present their timeline for the class to aid in discussing the nature of change in culture.