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Teaching Guide

Teaching The Phantom Tollbooth

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The Phantom Tollbooth is like a literary TARDIS, a little book that's much larger on the inside, jam-packed with endless learning opportunities across the curriculum. Our teaching guide is a lot like that, too. It seems small on the outside, but you might get lost once you step in.

In this guide you will find

  • a Phantom Tollbooth WebQuest.
  • related lessons about other literature…and even math.
  • additional resources, like interviews with the author about his writing process.

And much more.

With your help, your students will have all the resources they need to cover any toll.

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Inside each guide you'll find quizzes, activity ideas, discussion questions, and more—all written by experts and designed to save you time. Here are the deets on what you get with your teaching guide:

  • 13-18 Common Core-aligned activities to complete in class with your students, including detailed instructions for you and your students. 
  • Discussion and essay questions for all levels of students.
  • Reading quizzes for every chapter, act, or part of the text.
  • Resources to help make the book feel more relevant to your 21st-century students.
  • A note from Shmoop's teachers to you, telling you what to expect from teaching the text and how you can overcome the hurdles.

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Instructions for You

Objective: If you've never before done a WebQuest with your students, you're in for a treat. If you have done a WebQuest with your students, you're still in for a treat. WebQuests are a marvelous way for students to get information for themselves. Because the resources are already selected for them, they don't waste time searching for information; they spend their time using it. Here's a bonus: no wild goose chases for your students! They will expand their knowledge of Norton Juster, idioms, and wordplay—all items related to The Phantom Tollbooth.

You can expect this activity to take one 50-minute class period.

Materials Needed: Some students may need a hard copy of the WebQuest in front of them. If students are recording their responses manually instead of typing directly into a Word document, they will need paper. Other than that, the only thing needed is Internet access.

Step 1: Introduce the WebQuest. You may have to give a general overview of WebQuests if your students have never done one. You can really play this up by talking about famous quests. Make it age-appropriate: sixth-graders may not be familiar with Jason's quest for the golden fleece, but they can relate to Carl and Russell's quest in the movie Up.

Step 2: Either place the students with a partner or allow them to choose their own. Like the Avengers, they are uniting against a common threat to the world…Okay, so they're not the Avengers, but they are joining forces because two brains working together are always better than one. It's okay to have a group of three if there are an odd number of students.

Step 3: Students can get started. It's that easy! If you're passing out hard copies of the WebQuest and a response sheet, make sure students have it before they begin. In our quest to keep it simple, we have included WebQuest questions in the "student" section of this activity – so just go on over and take a peek!

(California Core Standards for English Language Arts: 6th, 7th and 8th grade Integration of Knowledge and Ideas 7; Production and Distribution of Writing 4, 5, 6; Research to Build and Present Knowledge 7, 8; Range of Writing 10; Comprehension and Collaboration 1, 2)

Instructions for Your Students

Student intro: Frodo had a crew and a quest, Dorothy had a crew and a quest, and now you have a crew and a quest. A WebQuest, that is. For this activity, you are going to use the Internet to find the answers to questions about Norton Juster, idioms, and wordplay. Don't worry, you won't have to spend hours looking for information on the world wide web – we have picked out the websites for you.

Step 1: In groups of two, you will click the links provided to you below and search each website for the answer.

The Phantom Tollbooth WebQuest

Milo takes a great adventure to Lands Beyond and you're going to take a great adventure across the web. That's right – you're doing a WebQuest. For a nice change of pace, you don't have to listen to me; everything you're going to learn is coming from the Internet. For your WebQuest activity, you will explore topics that will be covered in class and in your reading. Enjoy your journey!

You will use the Internet to find the answers to questions about Norton Juster, idioms, and wordplay.


  1. Choose a partner.
  2. To find the answers, click on the links provided below each set of questions.
  3. Record your answers and turn them in.

WebQuest Questions

Norton Juster

  1. When and where was Norton Juster born?
  2. Mr. Juster has written other books. Name three of them.
  3. Fill in the blank: Mr. Juster says he is an amateur cook but a professional ________.
  4. In what other languages has The Phantom Tollbooth been published?
  5. How does Mr. Juster describe his life growing up?



  • What is an idiom?
  • How many words are in the English language? How crazy is that?
  • What does "kill two birds with one stone" mean?
  • In the space provided below, draw a picture of the literal meaning of an idiom you like.


Let's have a little fun. Click the following link to play a "paint by idioms" game.


  • List three types of wordplay.
  • What is the formal or technical word for "punning"?
  • During the time of its publication, why did literary critics worry that The Phantom Tollbooth was just for gifted children or adults?


Step 2: Record your answers.

Step 3: The fun and games don't end here. Now you are to write a 10,000-word research paper on Norton Juster's academic background and early influences. Okay, okay, we're just kidding! Wipe that sweat off your forehead. Just turn in your work and have lots of good fun that is funny.

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