The Phantom Tollbooth
61 pages • 2 hours read
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- Introduction-Chapter 2
- Chapters 3-8
- Chapters 9-13
- Chapters 14-15
- Chapters 16-20
- Character Analysis
- Symbols & Motifs
- Important Quotes
- Essay Topics
- Discussion Questions
Summary and Study Guide
In Norton Juster’s 1961 middle-grade fantasy adventure The Phantom Tollbooth , a bored young boy visits a magical land whose people suffer from a strange delusion and volunteers to find a source of wisdom that can heal them. The book is a touchstone for generations of young readers; it has sold nearly five million copies in more than a dozen languages and has been adapted for film, stage, and symphony hall.
Author Juster published a dozen books, including The Dot and the Line , which was adapted into a short film that won an Academy Award . Juster also was an architect who taught architecture and environmental design at Hampshire College. The book is illustrated by Jules Feiffer, who later won a Pulitzer Prize and an Academy Award for other works.
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The e-book version of the 2011 50th-anniversary edition forms the basis for this study guide.
Content Warning: One passage refers to a “midget,” an old use of the word that today is considered disrespectful.
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Milo is a bored kid who has lost interest in life. In his room, he finds a large package that contains a tollbooth. He drives his small electric car through the tollway into a strange and colorful realm, the Lands Beyond .
At a junction called Expectations , Milo meets the Whether Man , a functionary who can’t make up his mind and offers Milo no useful information about the country he has entered. Further along, Milo thoughtlessly takes a wrong turn and ends up stalled in the dark, gray, featureless Doldrums , whose inhabitants, the tiny Lethargarians , spend their time yawning and napping. A watchdog named Tock—his body a giant alarm clock—scatters the locals and introduces himself by scolding Milo about getting mindlessly stuck in the Doldrums. Milo begins to think random thoughts, and his car starts to run again.
Milo and Tock drive to Dictionopolis , a city that grows letters on trees. The letters are bought and sold at a crowded weekly Word Market. The two travelers meet the king’s five ministers of words and the Spelling Bee , a large insect that can spell almost any word. The Humbug , a big, well-dressed beetle, derides the Spelling Bee for having a useless skill, whereas the Humbug is an important friend of the king. The Spelling Bee accuses the Humbug of lying; they fall to fighting and, in the process, knock down most of the stalls at the market.
The police arrive, including Officer Shrift, a very short, squat man who promptly convicts Milo of mayhem and sentences him and Tock to six million years in prison. The two are placed in a dungeon cell, where they meet the Official Which , an elderly lady who once controlled which words were used by the people but instead trained everyone disastrously to silence.
The Which explains that the prince who founded the Kingdom of Wisdom had two sons, and each built a great city—Azaz founded Dictionopolis, and the Mathemagician erected Digitopolis . The sons fought over which was more important, words or numbers. Their sisters, the wise and beautiful princesses Rhyme and Reason, declared that both were equally important. Furious, the brothers imprisoned the princesses in the Castle in the Air . Until they’re released, the kingdom will lack Rhyme and Reason .
The Which shows Milo how to escape the cell. Milo and Tock attend a royal banquet in their honor, where guests make short speeches about food, which is quickly served to them. For dessert, everyone eats cakes made of half-baked ideas. Overstuffed, the guests depart at once for dinner.
King Azaz frets about how ridiculous things have become in his city. Milo suggests he bring back Rhyme and Reason, but the king says it’s impossible. The Humbug suggests that, though extremely perilous, the journey to retrieve the princesses is doable if Milo and Tock attempt it. Delighted, the king appoints the Humbug as their guide and gifts the boy with a box filled with all the words Azaz knows: Properly used, they’ll get him through any difficulty.
The trio drives toward Digitopolis. On the way, they enter the Forest of Sight , where they meet a boy, Alec, who floats in the air because his legs haven’t yet grown long enough for his feet to touch the ground. Alec escorts them through the Forest, where they meet an ordinary man who’s the world’s smallest giant, thinnest fat man, and largest thin man. They also see a beautiful, imaginary city called Illusions and travel through an invisible city called Reality. They watch as a 1,000-person orchestra plays all the colors of day and night.
Beyond the Forest lies the Valley of Sound , where Milo and friends encounter the crashing sounds produced by Dr. Dischord and his noisy assistant, the awful Dynne. Deeper in the valley, there are no sounds at all, and people can only communicate by writing. The Soundkeeper reigned wisely over this land until it became too crowded, and people stopped listening to beautiful sounds, after which she decreed that only silence would prevail.
Milo visits the Soundkeeper’s fortress, where every sound ever made is invented, dispersed, and then re-collected and archived. He smuggles out a sound that’s placed in a cannon and fired at the fortress, which collapses in a huge roar of all the sounds ever heard. Dynne collects and returns the sounds, and the Soundkeeper recants her edict of silence.
The trio’s journey takes them along the coast, where they each utter an unfounded assumption and jump to Conclusions, an offshore island. They must swim back across the icy Sea of Knowledge.
The trio arrives at a cave. Inside is the numbers mine of Digitopolis. Its owner, the berobed and feisty Mathemagician, shows them around while workers chop away at the walls, extracting number stones for polishing and export. The visitors then visit the Mathemagician’s study, where he shows them several amazing arithmetic tricks. He tells Milo that if he wants to visit the land of Infinity, he should climb a nearby set of stairs. Milo does so but soon realizes that it’ll take forever and gives up.
The Mathemagician agrees that Milo should search for the princesses. He gives the boy a small, pencil-shaped magic wand for the purpose. Milo, Tock, and the Humbug hike up into the Mountains of Ignorance. They meet several demons, including a dapper man with no face who traps them into doing pointless chores; a small, nervous, furry creature who tricks them into falling into a huge pit; and, after they escape, a giant who’s too scared to show himself but instead takes the shape of whatever landscape he’s on.
Chased by demons, the three travelers find a stairway into the clouds and climb its windy, treacherous spiral to the Castle in the Air. Here, they find the princesses Rhyme and Reason waiting for them. The demons chop down the staircase, and the Castle drifts off through the sky. Tock, who can fly, carries the others as they leap from the Castle and float down toward the ground.
Demons pursue the group across the land of Ignorance, but the visitors escape into the Kingdom of Wisdom, where a giant army drives the demons back into the mountains. With the return of Rhyme and Reason, the kingdom celebrates for three days, feting Milo, Tock, and the Humbug as heroes.
Milo returns through the tollbooth to his bedroom. The next day after school, the tollbooth is gone. In its place is a note that assures the boy he’ll find his way to more adventures. Milo looks forward to enjoying the wonders of every day ahead.
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Action & adventure.
Brothers & Sisters
Jewish american literature, order & chaos.
The Phantom Tollbooth
By norton juster, the phantom tollbooth study guide.
The Phantom Tollbooth is a children's book written in 1961 by Norton Juster , an architect with a passion for planning, order, and, especially, maps. Basing the main character, Milo , on himself, Juster created an adventure story filled with philosophy, mathematics, and clever wordplay disguised as a fantastical tale of heroism and bravery where the child is the hero and the adults are forever in his debt. By making concepts such as boredom, jumping to conclusions, and color into actual people or places, Juster teaches his readers the importance of being interested in everything because one never knows when it might be useful.
Juster has mentioned several things that went into the book’s conception and writing. First, he submitted a grant to do a children’s book on urban aesthetics but found himself weary of the task. One day at Fire Island beach, where he was vacationing with friends, taking a break from the project, he decided to direct his attention to a little story germinating in his mind – the story of Milo, a bored kid, and his adventures in knowledge. Second, Juster was inspired by an event that took place a few days prior to his beach trip: a ten-year-old boy sat down next to Juster in a restaurant and asked him what the biggest number in the world was. Juster told him to think of the biggest number he knew and then to add one to it. The game continued back and forth until the boy left and Juster began to remember what it was like to be a child with so many burning questions and confusion about words and numbers. He also remembered feeling annoyed by having to study so many things that seemed irrelevant to him as a child and thus decided to write a short story about a child's confrontation with numbers and words. Finally, he stated that he was also inspired to write the book so he could have a map in it like the "Swallows and Amazons" books by Arthur Ransome that he has loved so much as a child.
Juster was renting a small apartment in Brooklyn in the 1960s due to his Navy allowance, and befriended Jules Feiffer, a cartoonist and screenwriter who also resided there. Feiffer remembered hearing his friend pacing at night above him, and when he confronted him on it he learned about the manuscript. Feiffer loved it and encouraged Juster, who from that point forward showed him the latest pages. Feiffer began to haphazardly illustrate, but it was not an official agreement that he’d illustrate the book from the beginning. In an interview Juster stated that he wrote the book from a variety of angles, focusing on different episodes at a time. When he was about 50 pages in, he submitted it to Random House and it was slated for publication.
The book was well-received upon its publication. In the New York Tribune, John Crosby wrote, “In a world which seems to have gone mad, it is refreshing to pause and consider for a moment a book for children which contains a character called ‘ Faintly Macabre ,’ the not so wicked witch.” Jane Jacobs also lauded the work in The Village Voice. However, some critics claimed it was not a children’s book because the vocabulary was beyond them. Others firmly believed that fantasy was bad for children because it disoriented and distracted them. It was adapted into a film that was popular but not particularly admired by Juster, who thought it was too slavishly devoted to the text.
The Phantom Tollbooth only grew in popularity over time, especially after an effusive New Yorker review. It became a mainstay of children’s literature, a bestseller, and the epitome of intelligent, witty fantasy for young people.
The Phantom Tollbooth Questions and Answers
The Question and Answer section for The Phantom Tollbooth is a great resource to ask questions, find answers, and discuss the novel.
Chapters 9-10 before you. Read
Are you referring to chapter 9 or 10?
What decree does soundkeeper issue
Since people had stopped appreciating sound, the Soundkeeper issued a decree abolishing all sound in the valley. The people in the crowd tell Milo that the Valley of Sound has been silent ever since.
Study the word rigmarole. Why did the count pass the breadbasket when offering a rigmarole?
I think that in this context, a rigmarole is a kind of croissant passed in a breadbasket.
Study Guide for The Phantom Tollbooth
The Phantom Tollbooth study guide contains a biography of Norton Juster, literature essays, quiz questions, major themes, characters, and a full summary and analysis.
- About The Phantom Tollbooth
- The Phantom Tollbooth Summary
- Character List
Lesson Plan for The Phantom Tollbooth
- About the Author
- Study Objectives
- Common Core Standards
- Introduction to The Phantom Tollbooth
- Relationship to Other Books
- Bringing in Technology
- Notes to the Teacher
- Related Links
- The Phantom Tollbooth Bibliography
Wikipedia Entries for The Phantom Tollbooth
- Influences and comparisons
- My Storyboards
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The Phantom Tollbooth by Norton Juster
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.
Student Activities for The Phantom Tollbooth
Essential Questions for The Phantom Tollbooth
- Why do people explore?
- Is it important to have an imagination? Why or why not?
- What influences our identity?
- What makes a person a hero?
A Quick Summary of 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.
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Frequently Asked Questions About The Phantom Tollbooth by Norton Juster
What is the phantom tollbooth about, who wrote “the phantom tollbooth”, what knowledge does milo acquire throughout his journey, try 1 month for.
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More on The Phantom Tollbooth
Introduction see all, summary see all, themes see all.
- Language and Communication
- Philosophical Viewpoints
- Freedom and Confinement
- Cunning and Cleverness
- Versions of Reality
Characters See All
- Rhyme and Reason
- The Mathemagician
- The Soundkeeper
- Faintly Macabre
- The Dodecahedron
- King Azaz's Cabinet
- The 0.58 Boy
- Officer Shrift
- The Lethargarians
- Chroma the Great
- Dr. Dischord and the DYNNE
- The Spelling Bee
- Minor Characters
Analysis See All
- What's Up With the Title?
- What's Up With the Ending?
- Writing Style
- The Phantom Tollbooth
- The Doldrums
- The Castle in the Air
- The Tollbooth
- Narrator Point of View
- Plot Analysis
Quotes See All
- For Teachers
The Phantom Tollbooth Introduction
A book about learning? Yuck – no, thank you. Next?
Wait a second, not so fast. The Phantom Tollbooth is here to show you, once and for all, that learning can be fun (whoa, just like Shmoop!). Imagine if you had a magic pencil to math your way out of sticky situations, or a box of words that helped you defeat evil demons. Sounding a little better, right?
Here's the deal: The Phantom Tollbooth tells the story of a bored kid named Milo, who takes an exciting journey through a magical kingdom, and in the process learns that life (and learning, too) isn't so boring after all. In fact, Shmoop would argue that every single word in this book is fun. Don't believe us? Take a look for yourself.
We've got magic, demons, a young hero, and a general spirit of fun and awesomeness. You younger readers have probably already bolted off to the library to get your hands on a copy of this gem. But for those of you more cynical fun-isn't-for-me types, read on. Ann McGovern, who wrote a rave review for the New York Times when the book was first published, gushed, " Norton Juster 's amazing fantasy has something wonderful for anybody old enough to relish the allegorical wisdom of 'Alice in Wonderland' and the pointed whimsy of 'The Wizard of Oz'" ( source ). We're totally with her. The allegories of The Phantom Tollbooth add a layer of learning that even the wisest of adults can appreciate.
Sure, the book was published in 1961, but guess what? Learning is still fun. And as long as you open your mind to it, it always will be. The Phantom Tollbooth didn't rack up many awards, but it won the most important prize of all: the enduring love of its readers.
What is The Phantom Tollbooth About and Why Should I Care?
Do you ever get bored in class? Antsy at dinner with your family? Do you have a room full of stuff and nothing to do? (Yeah, us too). It can be kind of a bummer, but it definitely helps us identify with our protagonist, Milo. He's almost lethally bored with everything. School's the worst for him – he's totally uninspired by learning things – but relaxation time isn't much better.
Luckily for Milo, rescue appears, in the form of a tollbooth. He drives through it and – BAM! – life's not boring any more. Wouldn't it be cool to go home and find one of these in your own room? Be able to drive through it and go on an adventure of your own? Well, guess what: you don't even need a tollbooth. You just need this book.
After all, when Milo gets back from his journey, he's still got all the tools he needs to have another great adventure any time he wants: they're all inside his head. And because we were along for the ride, we have all have those same tools. We can make the same discoveries Milo does: it's just a matter of viewing the world around us with hope and excitement. We learn a lot of lessons from The Phantom Tollbooth, but Shmoop's favorite is that learning and imagination can take us anywhere.
PS: If you're thinking that Milo's story, which was written in the 1960s, doesn't apply to you, we think you should give it another shot. And author Norton Juster agrees with us: "Today's world of texting and tweeting is quite a different place, but children are still the same as they've always been. They still get bored and confused, and still struggle to figure out the important questions of life" ( source ). Boredom is boredom, and adventure's adventure, no matter what year it is.
The Phantom Tollbooth Resources
For the Phans Check out the inside dirt on The Phantom Tollbooth at this site, which advertises an in-depth documentary about the book.
Wordplay Michael Chabon riffs on his first reading of The Phantom Tollbooth (this is also part of an introduction to the novel as published by Knopf).
The Phantom Tollbooth , Animated The 1970 movie version of the book, directed by Chuck Jones, is partly in cartoon form. We think that's kind of fitting.
The Phantom Tollbooth : 2013 Yes, please!
Original New York Times Review Ann McGovern raves about The Phantom Tollbooth when it first came out. Throwback!
Fifty Years Later Adam Gopnik takes his stab at The Phantom Tollbooth : the fiftieth anniversary of the book really sparked a lot of talk. And we couldn't be happier.
Interview with the Man Salon.com's Laura Miller talks with Norton Juster about The Phantom Tollbooth , the writing process, and life in general. We like this guy.
Old School Trailer Here's a preview of the 1970 movie, although we recommend checking out the whole thing. What do you think? Is that how you pictured the Lands Beyond?
Preview the musical! This YouTube short gives you an idea of what the full-length musical (music and lyrics by Sheldon Harnick and Arnold Black) is like. Pretty impressive.
Have a Listen David Hyde Pierce takes a stab at it: how do you think he did? (If you like it, you can buy the whole thing on Amazon.com !)
The Original This cover illustration – now a classic – was done by Jules Feiffer.
This is Definitely from the 70s What do you think: does this poster make you want to check out the film version?
Milo Down in the dumps.
The Lands Beyond This map often appears as the frontispiece (that's the fancy way of saying the picture at the front of a book) of The Phantom Tollbooth .
The Phantom Tollbooth Introduction Study Group
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Extend the Lesson with These Phantom Tollbooth Activities for the Elementary Classroom
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
- Poster supplies, such as markers and posterboard
Students can be given choices from among these activities at the teacher’s discretion.
- 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.
- Norton Juster has a very descriptive writing style. Find ten examples of similes and ten examples of metaphors from the book.
- 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.
- 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.
- 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.
The Phantom Tollbooth
Norton juster, everything you need for every book you read., king azaz the unabridged, the mathemagician.
Princess of Sweet Rhyme
Princess of pure reason, the soundkeeper, officer shrift, faintly macabre, the whether man, the lethargians, the spelling bee, the giant, midget, thin man, and fat man, dr. kakofonous a. dischord, the dodecahedron, terrible trivium, the demon of insincerity, the gelatinous giant, the official senses taker.