Extend the Lesson with These Phantom Tollbooth Activities for the Elementary Classroom

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The Phantom Tollbooth, by Norton Juster, is a great read for students in upper elementary grades and older. The story’s main character, Milo, learns a great lesson about his role in his own feelings of boredom. He enters a fantastic world through a mysterious tollbooth, interacts with a host of intriguing characters, and discovers that boredom is largely in the eye of the beholder. By the end of the story, he changes from a bored and somewhat spoiled child to a young man who sees nothing but possibilities in his world. In short, he learns to tap into his imagination. It’s a great lesson for kids of all ages, especially in this day and age when many children look to outside circumstances for their happiness instead of relying on their internal skills.

This lesson plan offers ideas to use with The Phantom Tollbooth. Extended activities included will help students to improve comprehension and make real world connections. Ideally students will have their own copies of the book or at least copies that can be shared among small groups.

Lesson Objectives and Materials

The objectives for these The Phantom Tollbooth extended activities are as follows:

  • Students will use a thesaurus.
  • Students will write sound sentences.
  • Students will increase vocabulary.
  • Students will identify similes and metaphors.
  • Students will recognize homonyms.
  • Students will analyze humor based on homonyms.
  • Students will write an essay in standard format.
  • Students will proofread written work.
  • Students will create a well-written paragraph with topic, supporting and closing sentences.


Choose the items you will need for activities you plan to offer.

  • Paper/pencil for all
  • Joke and riddle books, assorted
  • Thesauruses
  • Poster supplies, such as markers and posterboard


Students can be given choices from among these activities at the teacher’s discretion.

  1. King Azaz had five remarkable ministers who never used one word when five would do. They each repeated the same idea using synonyms. Out in the real world, we can use a thesaurus to find the same kinds of words that have similar meanings. Using less common words can add interest to writing and allow you to express exactly the right thought. It also prevents us from overusing plain, common words. Use a thesaurus to find five synonyms for these common words, just as the king’s ministers do: said, blue, round, fat, thin, went, try, saw, tall, big. Now, you should have fifty great words to choose from! Pick one from each group and work it into a sentence.
  2. Norton Juster has a very descriptive writing style. Find ten examples of similes and ten examples of metaphors from the book.
  3. The Whether Man wasn’t the usual sort of meteorologist. The book’s author made a play on words based on homonyms, the words that sound the same but have different spellings and meanings. Many jokes and riddles rely on the same type of humor. Grab a few joke books and find ten riddles or jokes that rely on homonyms for their laughs. Make a poster to show the jokes you found.
  4. The Mathmagician claimed to have a Magic Pencil that could perform all kinds of tricks. He made things disappear, multiply himself, and much more. Real pencils are pretty magical too, when you think about them. Write an essay to persuade your audience that pencils are the most important tools ever invented.
  5. What happened when Milo, Tock and the Humbug met the Terrible Trivium? Think of ten time wasters in your own life that seem to have come from the Terrible Trivium. How can you get rid of them? Write a paragraph.

Evaluation and Extension Activities

Evaluate students' efforts by assessing their finished products according to grade level standards.

If additional activities are desired, try these:

  • Challenge students to create a vocabulary lesson to teach to their peers based on the Phantom Tollbooth. Choose twenty words from the text to teach and make at least three worksheets or games that students could use to practice them.
  • Write the story of what happened to the tollbooth after it disappeared from Milo’s room. Who used it next? Where did it go and what adventures happened?
  • Create a Venn Diagram to compare and contrast King Azaz with the Mathmagician.
  • Write down fifteen plot events in proper sequence from the story.
  • Analyze the Phantom Tollbooth for themes and other literary elements.