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.

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.

Plot Summary

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.