The Phantom Tollbooth cover

The Phantom Tollbooth

by Norton Juster

The Phantom Tollbooth is a children's fantasy adventure novel written by Norton Juster with illustrations by Jules Feiffer. It was published in 1961 by Random House (USA). It tells the story of a bored young boy named Milo who unexpectedly receives a magic tollbooth one afternoon and, having nothing better to do, drives through it in his toy car, transporting him to the Kingdom of Wisdom, once prosperous but now troubled. There, he acquires two faithful companions, a dog named Tock and the Humbug, and goes on a quest to restore to the kingdom its exiled princesses—named Rhyme and Reason—from the Castle in the Air. In the process, he learns valuable lessons, finding a love of learning. The text is full of puns and wordplay, such as when Milo unintentionally jumps to Conclusions, an island in Wisdom, thus exploring the literal meanings of idioms.

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Chappie’s discussion starters

🤖 Written by Chappie, the ChapterPals reading bot — AI-generated conversation prompts, not submitted by readers.

  1. Which character stayed with you after you turned the last page, and why?
  2. Was there a moment where you disagreed with a character’s choice? What would you have done?
  3. What theme did this book keep circling back to — and did it earn its ending?
  4. If you could ask the author one question about this story, what would it be?
  5. Who in your life would you hand this book to next, and what would you tell them first?