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Teaching Guide

Teaching The Phantom Tollbooth

Transport your class with Shmoop.


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.

What's Inside Shmoop's Literature Teaching Guides

Shmoop is a labor of love from folks who love to teach. Our teaching guides will help you supplement in-classroom learning with fun, engaging, and relatable learning materials that bring literature to life.

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.

Instructions for You

Objective: If you've never 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, which means no wild goose chases.

On this WebQuest, they will expand their knowledge of Norton Juster, idioms, and wordplay—all items related to The Phantom Tollbooth.

Length of Lesson: You can expect this activity to take one 50-minute class period.

Materials Needed: 

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: fifth-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 or Anna's quest in Frozen.

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! Just set them up with the student instructions, give them an answer sheet to fill in, and go. In our quest to keep things 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

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. 

Just as Milo took a great adventure to Lands Beyond in  The Phantom Tollbooth, you're going to take a great adventure across that vast land called the Internet. You'll work with a partner to find 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 the websites all picked out for you.  

Step 1: Take a minute to chat with your teacher and the rest of your class about the whole WebQuest idea to make sure you know what you're doing and how long you have to do it. The questions you'll need to answer are all below, and for each set of questions, we've included a set of links that will provide you with everything you need to come up with the answers. 

Step 2: If you were paying attention, you probably noticed that we mentioned you'll be working with a partner. So... go ahead and find one! (If there are an odd number of students in your class, there will need to be one group of three.)

Step 3: Get a copy of Shmoop's Phantom Tollbooth Webquest Answer Sheet from your teacher so you have a place to record your answers. Then get started. Your quest awaits—and your questions are below. Good luck! 

WebQuest Questions

Part I: 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?

Norton Juster's Biography
NJ on GoodReads
Interview with NJ on Underdown.org
Interview with NJ on AVClub

Part II: Idioms

  1. What is an idiom?
  2. How many words are in the English language? How crazy is that?
  3. What does "kill two birds with one stone" mean?
  4. Draw a picture of the literal meaning of an idiom you like.

Idiom Site
20 Most Common Idioms in English
Literal Pictures of Idioms by Kids (scroll down for the list)

Let's have a little fun. Click below to play an idiom-inspired game.

Paint by Idioms

Part III: Wordplay

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

Fun With Words
Dictionary.com on The Phantom Tollbooth
Los Angeles Review of Books Talks TPT

Step 2: Go over your answer sheet and make sure you've recorded all of your answers.

Step 3: You journeyed into unknown lands and made it back in one piece. Nice work. Now turn in your answer sheet and set off on a new quest of your own. Be sure to have lots of good fun that is funny.

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Common Core Standards  


Check out all the different parts of our corresponding learning guide.

Intro    Summary    Themes    Quotes    Characters    Analysis    Questions    Quizzes    Flashcards    Best of the Web    Write Essay    
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