100 Sideways Miles Reading Guide & Discussion Questions

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100 Sideways Miles by Andrew A. Smith

100 Sideways Miles

by Andrew A. Smith
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  • Critics' Consensus (6):
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  • First Published:
  • Sep 2, 2014, 288 pages
  • Paperback:
  • Sep 2015, 304 pages
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Book Club Discussion Questions

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For supplemental discussion material see our Beyond the Book article, William Mulholland and the St. Francis Dam and our BookBrowse Review of 100 Sideways Miles.


Please be aware that this discussion guide will contain spoilers!

After losing his mother at a young age in a bizarre accident that left him with a broken back and epilepsy, Finn has been coping but never quite feeling up to meeting life's challenges. With the help of his charismatic best friend, Cade, a heroic rescue in which the two boys ultimately rescue themselves, and the risk of romance with Julia, Finn begins to see everything differently.

Prereading Discussion

Read Maya Angelou's poem Caged Bird. Pay particular attention to images of clipped wings and shadow. Why does the caged bird sing?

Discussion Questions

  1. Finn thinks about time in terms of space. He wonders about cosmological concepts and principles that hold the universe together. What does Finn's fascination with the cosmos reveal about him?
  2. What does it mean to be trapped in a book? Have you ever felt trapped? How so?
  3. Finn comments, "When you think about it, the universe is nothing but this vast knackery of churning black holes and exploding stars, constantly freeing atoms that collect together and become something else, and something else again." What does Finn mean by this?
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  1. How does the author develop themes of identity and belonging throughout the narrative?
  2. What role does the setting play in shaping the characters' decisions and relationships?
  3. Discuss how the ending reframes the events of the story. Were you surprised?


Unless otherwise stated, this discussion guide is reprinted with the permission of Simon & Schuster Books for Young Readers. Any page references refer to a USA edition of the book, usually the trade paperback version, and may vary in other editions.

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