The Legend of Sleepy Hollow

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"The Legend of Sleepy Hollow" is a short story by American author Washington Irving, contained in his collection of 34 essays and short stories entitled The Sketch Book of Geoffrey Crayon, Gent. Written while Irving was living abroad in Birmingham, England, "The Legend of Sleepy Hollow" was first published in 1820. (From Wikipedia)
Curriculet Details
15 Questions
18 Annotations
1 Quiz

This free digital curriculum for high school students contains interactive videos exploring character development and plot structure, as well as annotations describing setting and archetypes. Students will explore the themes of superstition, outsiders, and heroism. The Common Core aligned questions, answers and quizzes in this free online unit will increase student engagement in the short story while supporting reading comprehension.

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The Legend of Sleepy Hollow

Washington Irving chooses to open this short story with a passage from James Thomson's poem, "Castle of Indolence." Notice the poet's word choice: "pleasing," "dreams," "drowsy," "half-shut eye," and "indolence," for example. Words such as these help set the mood and establish the setting for Irving's famous story about the lovely yet mysterious hamlet of Sleepy Hollow, New York. As you read Irving's description of this area, compare the words he chooses with the words of the opening poem.  
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What does this passage lead the reader to understand about this part of New York? 
Did you know that you can look up any word in the text of the book or the text of the questions and answers? Just click (or press on mobile devices) the word you want to define and hold until the blue text selector pops up. When you release, a define option will appear. Since it's so easy to look up words, make sure you use this feature frequently. Try it now with the word "Hessian." What does this term help you understand better about the figure that "haunts this enchanted region"? 
The tale of the Headless Horseman is not one Irving created; instead, similar characters appear in several earlier European folk tales. Thanks to the popularity of this story, though, the Headless Horseman of Sleepy Hollow, assumed to be the ghost of a Hessian soldier, is the most well-known today. The picture below shows what has been dubbed "America's Scariest High School Mascot." Observe the photograph carefully and then answer the question that follows. (This annotation contains an image)
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How does the mood of the above photograph compare with the author's tone as he describes the Headless Horseman in this story? Use details from both the text and photograph to support your answer. 
The author uses a mixture of direct and indirect characterization throughout the story to describe the protagonist, Ichabod Crane. Here, Crane's physical appearance is directly described in detail, but what can indirectly be inferred about the character as well? Use the character's name, actions, thoughts, and motivations to fully understand complex characters you encounter while reading.  
The author uses a hyperbole in this passage to show just how big of an appetite Ichabod Crane has. For more about the use of hyperboles, watch the video below. Why do you think the narrator includes such an unexpected and bold detail to describe Ichabod?  (This annotation contains a video)
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Based on details from the text, which of the following is most likely to be true about Ichabod Crane as this story begins? 
In another example of direct characterization, the narrator makes it clear that Ichabod is a relatively intelligent man, but he is prone to superstition and fantasy. How might "this spell-bound region" of Sleepy Hollow, to which he is an outsider, affect the character of Ichabod Crane? As you read, look for evidence of both Crane's superstitions and the village's eerieness. 
The idea of "fearful pleasure" is a type of contradiction known as a paradox. One of the most famous literary paradoxes is shown below. While Ichabod enjoys hearing these ghost stories, especially ones about the Headless Horseman, they also have a dreadful effect on him later when he is alone. Like the statement below, he feels two conflicting emotions at the same time. As you read, look for ways in which this detail will help you understand both the character and the developing plot. (This annotation contains an image)
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Which of the following words in this passage do not help set the mood that affects Ichabod when he walks alone in Sleepy Hollow? 
In this passage, the narrator clearly establishes conflict. While Ichabod is a fearful and superstitious person living in a mysterious place, according to the narrator, the bigger conflict is actually about a woman. Therefore, this story will contain both internal and external conflict. To better understand each type of conflict and how both affect the plot and characterization, watch the video below. How do both types of conflict develop in this story? (This annotation contains a video)
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According to details from the text, which of the following is Ichabod's main desire regarding the Van Tassel family? 
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While other types of archetypes exist, what Jungian archetype does Brom Bones most clearly represent? 
The "burly," manly character of Brom Van Brunt is clearly a contrast to the meeker Ichabod Crane. Again, pay attention to both direct and indirect characterization to understand this new character. Both Brom and Ichabod also represent archetypes that are often seen in literature. Click the link to read more about Carl Jung's specific concept of archetypes. Then, answer the question that follows.  (This annotation contains a link)
This passage contains an example of an extended metaphor. Rather than quickly compare Ichabod to a supple-jack, the narrator goes into detail about both. How does an extended metaphor add detail that a simple metaphor does not? Use the image below to better understand this type of figurative language.  (This annotation contains an image)
The narrator of this story is never actually introduced to the reader here, but in a companion piece to "The Legend of Sleepy Hollow," we learn that his name is Diedrich Knickerbocker. Although he does not actively figure into the action of this story, it is most often considered to be told from first person point of view since the narrator uses pronouns such as "I" and "me." To better understand the use of point of view, including cultural perspective, watch the video below. How might this story be different if the first person point of view were that of a true Sleepy Hollow resident or even Ichabod himself? (This annotation contains a video)
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Why does Brom play jokes on Ichabod Crane? 
Compare the description in the text of Ichabod and his horse with the image shown below. How is the tone, or attitude, of both works somewhat comical? (This annotation contains an image)
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How does the fine autumn weather affect Ichabod Crane? 
Notice that Ichabod Crane is described here by the narrator as a "hero." Yet, if the narrator is using verbal irony, Ichabod is sometimes considered by literary critics to be more of what is often called an anti-hero. Click the link below to compare and contrast the two character types. As you continue to observe his character development, decide whether or not you think Ichabod is heroic.  (This annotation contains a link)
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How does the author create a sense of increasing conflict and tension within this passage? 
Compare the text with the video below, then answer the question that follows.  (This annotation contains a video)
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How does the video of the "dismal tales" told at Van Tassel's compare with the description in the text? Use specific details from each representation of the scene. 
This paragraph contains several examples of foreshadowing, which means it's a great time to make some predictions as you approach the climax of the story. If the ghost stories "sank deep in the mind of Ichabod" and he repays the crowd (including his rival) by telling them of his own "fearful sights," what is likely to happen after the party breaks up? Notice how the author uses details in this passage to increase the tension and heighten the story's suspense.  
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Based on details from the text, what can you infer happens to Ichabod at the end of the party? 
Major John Andre was captured in this region of New York and executed as a British spy and co-conspirator of Benedict Arnold during the American Revolution. See the plaque below. Where else in this short story have you seen an overlap between truth and fiction?  (This annotation contains an image)
The author uses careful word choice in this part of the story to heighten the tension of the scene. There are also several "near-misses," in which Ichabod thinks he sees something that turns out to be nothing. To understand more about how an author heightens tension, watch the video below. What specific words does the author use to intensify the mood? (This annotation contains a video)
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What specific detail causes Ichabod to burst into action? 
Compare the details in the text with the famous 19th century painting below. Which textual details seem to have inspired the painter? What details would you add to your own treatment of the scene? (This annotation contains an image)
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What detail from this passage could lead the reader to believe that Ichabod did not actually encounter a ghost? 
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Why does the author most likely include this detail about Brom Bones in the story's conclusion? 
Quiz, The Legend of Sleepy Hollow 
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Now that you have read the entire story, why do you think the author chooses not to have the story told from Ichabod's point of view? What effects are achieved by the use of an outside narrator?