Phantom Tollbooth Assignments

Student Activities for The Phantom Tollbooth Include:

The Phantom Tollbooth is a fantasy novel about a young boy named Milo who was always unsettled and unable to find purpose in life. One day, a mysterious tollbooth appears and transports him to a life of magic, adventure, and wonder.

A Quick Plot Synopsis The Phantom Tollbooth

The Phantom Tollbooth begins by introducing Milo, a young boy, bored by life, who has no interest or motivation to learn or do anything. He notices a mysterious package in his room containing a tollbooth and a map. Deciding he has nothing better to do, he builds the tollbooth, climbs into his toy car, and drives through. Milo immediately finds himself driving along a mysterious road in a strange environment. Before long, he comes to Dictionopolis, a strange city inhabited by King Azaz, and citizens who have a fascination with words.

As Milo enters this imaginary land of Dictionopolis, he quickly realizes that everything is peculiar - including his encounter with a talking watchdog named Tock. Tock continues on the voyage with Milo to Dictionopolis where they discover a kingdom of words and letters: five gentlemen provide synonyms of words, a Spelling Bee spells out words, and people eat words.

Spelling Bee and Humbug, a foolish people-pleaser, get into an argument in the marketplace. During the quarrel, Humbug accidentally knocks over all the tables in the marketplace, which causing chaos. Milo is accused by Officer Shrift of being the culprit, and is sentenced to prison for six million years. In prison, Milo and Tock meet Faintly Macabre, the not-so-wicked “Which”. Faintly Macabre shares the story of how everything came to be: a young prince sailed the Sea of Knowledge, built the Kingdom of Wisdom, and had a wife and two sons. These sons went their separate ways and created two lands, Dictionopolis and Digitopolis. A rift occurred between the family as the two sons attempted to outdo the other, one swearing that words were better, and the other swearing that numbers were better. The king also had adopted two beautiful girls, Rhyme and Reason. These girls grew up in Wisdom and were able to solve all disagreements and problems that were brought to them. The two brothers became outraged when Rhyme and Reason would not claim one of them as correct, so they banished the sisters to the Castle in the Air. Milo decides that he is going to help set Rhyme and Reason free.

Milo and Tock easily escape the prison, and, much to their surprise, are welcomed back into the kingdom. At the king’s banquet, Milo reiterates his wish to rescue the princesses. Humbug agrees to accompany Milo and Tock on the long, treacherous adventure through distant kingdoms, including Digitopolis and Mountains of Ignorance.

During their voyage, Milo, Tock, and Humbug, meet many strange characters and learn about the mysteries of the land: people growing down, an orchestra that controls the light in the sky, unpleasant sounds being created and captured, and the Silent Valley where no sounds are heard at all. Milo presses forward to rescue the princesses who will be able to solve all the land’s problems.

The three travelers find their way to Digitopolis, the land of numbers. Here, equally bizarre and magical occurrences push Milo to reach the princesses and set everything right. It isn’t easy; demons and giants chase Milo, Tock, and Humbug to the gates of the Castle in the Air, and are only stopped by the Armies of Wisdom. Everyone in the land congratulates the trio on the impossible success of their quest, with a parade and a three day carnival. At the end of the carnival, Milo is told he has to say goodbye and return home. A sad and disappointed Milo says farewell to his new friends.

When Milo returns home, he is sure his parents will be worried about him because he has been gone for so long. It turns out however, Milo had only been gone an hour. He returns to school the next day, bored as ever. When he returns to the tollbooth for another adventure, he finds has been replaced with a letter advising him that he can now travel to distant lands on his own. At first, Milo sits sadly at the window, but soon he opens his eyes to the possibilities of the world in front of him.

Essential Questions for The Phantom Tollbooth

  1. Why do people explore?
  2. Is it important to have an imagination? Why or why not?
  3. What influences our identity?
  4. What makes a person a hero?

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Teaching The Phantom Tollbooth

The Phantom Tollbooth lesson plan contains a variety of teaching materials that cater to all learning styles. Inside you'll find 30 Daily Lessons, 20 Fun Activities, 180 Multiple Choice Questions, 60 Short Essay Questions, 20 Essay Questions, Quizzes/Homework Assignments, Tests, and more. The lessons and activities will help students gain an intimate understanding of the text, while the tests and quizzes will help you evaluate how well the students have grasped the material. View a free sample

Target Grade: 7th-12th (Middle School and High School)

Length of Lesson Plan: Approximately 111 pages. Page count is estimated at 300 words per page. Length will vary depending on format viewed.

Browse The Phantom Tollbooth Lesson Plan:

Full Lesson Plan Overview

Completely Customizable!

The Phantom Tollbooth lesson plan is downloadable in PDF and Word. The Word file is viewable with any PC or Mac and can be further adjusted if you want to mix questions around and/or add your own headers for things like "Name," "Period," and "Date." The Word file offers unlimited customizing options so that you can teach in the most efficient manner possible. Once you download the file, it is yours to keep and print for your classroom. View a FREE sample

Lesson Plan Calendars

The Lesson Plan Calendars provide daily suggestions about what to teach. They include detailed descriptions of when to assign reading, homework, in-class work, fun activities, quizzes, tests and more. Use the entire The Phantom Tollbooth calendar, or supplement it with your own curriculum ideas. Calendars cover one, two, four, and eight week units. Determine how long your The Phantom Tollbooth unit will be, then use one of the calendars provided to plan out your entire lesson.

Chapter Abstracts

Chapter abstracts are short descriptions of events that occur in each chapter of The Phantom Tollbooth. They highlight major plot events and detail the important relationships and characteristics of important characters. The Chapter Abstracts can be used to review what the students have read, or to prepare the students for what they will read. Hand the abstracts out in class as a study guide, or use them as a "key" for a class discussion. They are relatively brief, but can serve to be an excellent refresher of The Phantom Tollbooth for either a student or teacher.

Character and Object Descriptions

Character and Object Descriptions provide descriptions of the significant characters as well as objects and places in The Phantom Tollbooth. These can be printed out and used as an individual study guide for students, a "key" for leading a class discussion, a summary review prior to exams, or a refresher for an educator. The character and object descriptions are also used in some of the quizzes and tests in this lesson plan. The longest descriptions run about 200 words. They become shorter as the importance of the character or object declines.

Daily Lessons

This section of the lesson plan contains 30 Daily Lessons. Daily Lessons each have a specific objective and offer at least three (often more) ways to teach that objective. Lessons include classroom discussions, group and partner activities, in-class handouts, individual writing assignments, at least one homework assignment, class participation exercises and other ways to teach students about The Phantom Tollbooth in a classroom setting. You can combine daily lessons or use the ideas within them to create your own unique curriculum. They vary greatly from day to day and offer an array of creative ideas that provide many options for an educator.

Fun Classroom Activities

Fun Classroom Activities differ from Daily Lessons because they make "fun" a priority. The 20 enjoyable, interactive classroom activities that are included will help students understand The Phantom Tollbooth in fun and entertaining ways. Fun Classroom Activities include group projects, games, critical thinking activities, brainstorming sessions, writing poems, drawing or sketching, and countless other creative exercises. Many of the activities encourage students to interact with each other, be creative and think "outside of the box," and ultimately grasp key concepts from the text by "doing" rather than simply studying. Fun activities are a great way to keep students interested and engaged while still providing a deeper understanding of The Phantom Tollbooth and its themes.

Essay Questions/Writing Assignments

These 20 Essay Questions/Writing Assignments can be used as essay questions on a test, or as stand-alone essay topics for a take-home or in-class writing assignment on The Phantom Tollbooth. Students should have a full understanding of the unit material in order to answer these questions. They often include multiple parts of the work and ask for a thorough analysis of the overall text. They nearly always require a substantial response. Essay responses are typically expected to be one (or more) page(s) and consist of multiple paragraphs, although it is possible to write answers more briefly. These essays are designed to challenge a student's understanding of the broad points in a work, interactions among the characters, and main points and themes of the text. But, they also cover many of the other issues specific to the work and to the world today.

Short Essay Questions

The 60 Short Essay Questions listed in this section require a one to two sentence answer. They ask students to demonstrate a deeper understanding of The Phantom Tollbooth by describing what they've read, rather than just recalling it. The short essay questions evaluate not only whether students have read the material, but also how well they understand and can apply it. They require more thought than multiple choice questions, but are shorter than the essay questions.

Multiple Choice Questions

The 180 Multiple Choice Questions in this lesson plan will test a student's recall and understanding of The Phantom Tollbooth. Use these questions for quizzes, homework assignments or tests. The questions are broken out into sections, so they focus on specific chapters within The Phantom Tollbooth. This allows you to test and review the book as you proceed through the unit. Typically, there are 5-15 questions per chapter, act or section.

Evaluation Forms

Use the Oral Reading Evaluation Form when students are reading aloud in class. Pass the forms out before you assign reading, so students will know what to expect. You can use the forms to provide general feedback on audibility, pronunciation, articulation, expression and rate of speech. You can use this form to grade students, or simply comment on their progress.

Use the Writing Evaluation Form when you're grading student essays. This will help you establish uniform criteria for grading essays even though students may be writing about different aspects of the material. By following this form you will be able to evaluate the thesis, organization, supporting arguments, paragraph transitions, grammar, spelling, punctuation, etc. of each student's essay.

Quizzes/Homework Assignments

The Quizzes/Homework Assignments are worksheets that can be used in a variety of ways. They pull questions from the multiple choice and short essay sections, the character and object descriptions, and the chapter abstracts to create worksheets that can be used for pop quizzes, in-class assignments and homework. Periodic homework assignments and quizzes are a great way to encourage students to stay on top of their assigned reading. They can also help you determine which concepts and ideas your class grasps and which they need more guidance on. By pulling from the different sections of the lesson plan, quizzes and homework assignments offer a comprehensive review of The Phantom Tollbooth in manageable increments that are less substantial than a full blown test.


Use the Test Summary page to determine which pre-made test is most relevant to your students' learning styles. This lesson plan provides both full unit tests and mid-unit tests. You can choose from several tests that include differing combinations of multiple choice questions, short answer questions, short essay questions, full essay questions, character and object matching, etc. Some of the tests are designed to be more difficult than others. Some have essay questions, while others are limited to short-response questions, like multiple choice, matching and short answer questions. If you don't find the combination of questions that best suits your class, you can also create your own test on The Phantom Tollbooth.

Create Your Own Quiz or Test

You have the option to Create Your Own Quiz or Test. If you want to integrate questions you've developed for your curriculum with the questions in this lesson plan, or you simply want to create a unique test or quiz from the questions this lesson plan offers, it's easy to do. Cut and paste the information from the Create Your Own Quiz or Test page into a Word document to get started. Scroll through the sections of the lesson plan that most interest you and cut and paste the exact questions you want to use into your new, personalized The Phantom Tollbooth lesson plan.

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