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So you’re going to teach Washington Irving’s short story “Rip Van Winkle.” Whether it’s your first or hundredth time, “Rip Van Winkle” has been a mainstay of English classrooms for generations. While it has its challenges—necessary historical context and multiple layers of narration—teaching this text to your class will be rewarding for you and your students. Studying “Rip Van Winkle” will give them unique insight into American Romanticism, frame stories, and the theme of tradition versus modernity. This guide highlights some of the most salient aspects of the text before you begin teaching.

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Facts at a Glance

  • Publication Date: 1819
  • Recommended Grade Level: 9-12
  • Approximate Word Count: 7,200
  • Author: Washington Irving
  • Country of Origin: United States
  • Genre: Short Story
  • Literary Period: American Romanticism 
  • Conflict: Person vs. Person, Person vs. Society
  • Narration: Third-Person Limited
  • Setting: Catskill Mountains, United States, 18th Century
  • Structure: Framed Narrative, Folktale
  • Mood: Whimsical, Mysterious, Satirical

Texts that Go Well with “Rip Van Winkle”

“The Devil and Tom Walker,” by Washington Irving, was published in the collection Tales of a Traveller in 1824. It is a short story, also narrated by Geoffrey Crayon, that follows the Tom as he sells his soul to the devil for monetary gain. Both “Rip Van Winkle” and “The Devil and Tom Walker” feature protagonists with ill-tempered wives who meet life-altering supernatural figures.

“June’s Coming” is a poem by John Burroughs, published in his 1906 collection Birds and Boughs. Burroughs (1837-1921) lived in the Catskill Mountains, and much of the poetry in Birds and Boughs is about the Catskills and surrounding area. Like “Rip Van Winkle,” “June’s Coming” gives an imagery-laden description of the Hudson River and nature of the Catskills.

“The Legend of Sleepy Hollow,” by Washington Irving, is another story from The Sketch Book of Geoffrey Crayon, Gent. and attributed to the papers of Diedrich Knickerbocker. Along with “Rip Van Winkle,” it is one of Irving’s best-known short stories. It also explores the lasting influences of Dutch culture and the American Revolution on small New England communities. The story shows the power of folklore within a community while expanding the American tradition Irving invented through Knickerbocker in “Rip Van Winkle.”

“Oisin and Niam” is a Irish tale of two lovers, eternal youth, and death. The tale exists in several forms, but a printed version can be found in T. W. Rolleston’s Celtic Myths and Legends, originally published in 1911. “Oisin and Niamh” pairs well with “Rip Van Winkle” in that both stories explore the effects of time-travel and age. Oisin leaves Ireland for 300 years, much as Rip misses the American Revolution during his twenty-year sleep. Both Oisin and Rip age greatly, although Oisin dies of old age whereas Rip Van Winkle lives on as an elderly man.

“The Secret Life of Walter Mitty,” (1939) by James Thurber, describes the vivid daydreams through which Walter Mitty escapes his mundane life. In contrast to the moments that spark them, his daydreams are wild and adventurous. Like Rip, Walter Mitty is gentle and mild-mannered. His story shows a character who willingly creates the dream-like circumstances that pull him away from his life.

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Key Plot Points