Name: _______________________
“Where the Horseman Haunts (Part 1)”
Directions: Answer the follow Critical Thinking Questions below in sentence form.
“The Legend of Sleepy Hollow” was written by Washington Irving as a satirical
response to a generation of people who he felt had lost their way in life. These people
were living in a world ruled by an industrial mindset—a world of black smoke,
pollution, greed, starvation, and poverty. Irving led a movement of authors and artists called Romanticism,
which wanted to take people back to a simpler time—a time of peace, virtue, imagination, and nature.
Irving’s creation of Sleepy Hollow embodied his view of a Romantic utopia—quiet, calm, and
seemingly free of stresses of the real world. The people were Dutch farmers, happy and content in their
existence and very creative in mind and spirit. They had remained true to their heritage for generations,
exhibiting great manners and unique, country customs.
1. What is your initial impression of the area of the world where Tarrytown (formal name for Sleepy
Hollow) is located and its people? Explain your impression using three characteristics that the author
gives us on pages 1-2. [5 points]
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2. A legend or story is not just great entertainment; but, they can be a very effective teaching (education) or
parenting (discipline) tool. In your opinion, how do the parents of Sleepy Hollow use the story of the
Headless Horseman? Why? [10 points]
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Name: _______________________
“Where the Horseman Haunts (Part 2)”
Directions: Read the following passage about the background on “The Legend of Sleepy
Hollow.” Answer the questions below in sentence form.
……Ichabod Crane, Washington Irving’s embodiment of the Industrial way of
thinking, entered the hollow as a schoolmaster and left as a legend. As awkward,
scarecrow looking man from Connecticut, Crane was completely opposite anyone
Sleepy Hollow had to offer or had ever seen. Unlike the well-muscled farmers, called the Sleepy Hollow Boys,
Crane was tall, thin, and wore clothes of a sophisticated taste. Despite his unique physical appearance he
possessed a giant appetite for food that was only rivaled by his yearning for money and to hear ghost stories.
Everything he saw was calculated with a price tag, including the farm of Baltus Van Tassel. He also loved to
immerse himself in the rich local stories of ghosts, goblins, and witches—particularly that of the Headless
Horseman, a Revolutionary War soldier who lost his head during battle.
3. What are some important traits that you’ve seen in your best teachers ever? Does Ichabod Crane have
those same traits? Why or why not? [5 points]
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4. How do you think the husbands of Sleepy Hollow reacted to the introduction of Ichabod Crane into their
community? Why? [10 points]
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Name: _______________________
“Where the Horseman Haunts (Part 3)”
Directions: Read the following passage about the background on “The Legend of Sleepy
Hollow.” Answer the questions below in sentence form.
. . . . . .Katrina had many men vying for her attention, throwing themselves at her.
These men were led by the ominous Brom Bones, a gigantic Dutch farmer, who
embodied Sleepy Hollow’s rough manner and its fun-loving spirit. He did not take kindly to the advances of
Ichabod Crane toward Katrina, especially when his time with her began to diminish to virtually nothing.
While Brom would have rather dueled with Crane in the manner of a gentleman, the schoolmaster avoided
his Herculean counterpart at all costs. Brom also feared the consequences of being viewed as a “brute” by
Katrina if he indeed did follow through in his promise to “double-up the schoolmaster and lay him on the
school-house shelf.” He did not want to do anything that would place him further from the heart of his love.
5. What is the reason for Ichabod’s intense cowardice of supernatural things that go “bump-in-the-night”
and his vivid fear of women?
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6. Explain why the following passage from page 6 illustrates Ichabod Crane as a symbol of the Industrial
Revolution: “From the moment Ichabod laid his green eyes upon these regions of delight, the peace
of his mind was at an end, and his only study was how to gain the affections of the peerless
daughter of Van Tassel.” [10 points]
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Name: _______________________
“Where the Horseman Haunts (Part 4)”
Directions: Read the following passage about the background on “The Legend of Sleepy
Hollow.” Answer the questions below in sentence form.
. . . . . .The rivalry between Bones and Crane would come to a head on All Hallows’
Even at the invite only party thrown by Baltus Van Tassel. Crane felt this would be
the night that he swept Katrina off of her feet with immense charm and even more
immense talent—dancing. On the way he dreamed of their future together. Once he arrived at the party, he
could neither contain his excitement at the sight of the buffet of culinary treasures, nor his curiosity at the
fireside stories being told by the old, Dutch farmers. They spoke of the areas deep history of ghosts, goblins,
and spirits that ruled the night, making even the bravest man pray for God’s watchful eye. While he wooed
the beautiful lady of the house, he left the party with a full stomach but an empty heart. Little did he know
that his ride home would soon be told by those same old, Dutch farmers around those same fireside chats for
years to come; he would not be there.
7. Explain Ichabod Crane’s daydream during the ride to the Van Tassel party on page 9. What earlier
“Industrialist” characteristic of Crane does Irving reinforce to the reader in these paragraphs?
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8. Do you think that Katrina Van Tassel had a legitimate interest in Ichabod Crane or did she use him as a
fool in her ultimate goal to “tame” the wild and mischievious Brom Bones? Why? [10 points]
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