Study Guide

The Phantom Tollbooth

The Phantom Tollbooth Summary

A young boy named Milo is going about his business, more bored than you could imagine. He doesn't like school and has nothing to do. (Or at least that's what it feels like). But in an exciting turn of events, he comes home one day to find a magic tollbooth in his room. He gets in his toy car, goes through the tollbooth, and finds himself in a magical place called the Lands Beyond. Now this is a story.

Milo starts by exploring a place called Wisdom and then passes through a region called the Doldrums, where everyone seems to be as bored as he was at home. He meets a watchdog named Tock, who joins him on his journey: together, they head to Dictionopolis where they meet a bunch of crazy characters who are obsessed with words. Yep, words. During a brief stint in jail (don't worry, it wasn't Milo's fault), Milo and Tock find out why Wisdom isn't so peaceful these days.

As it turns out, rival brothers King Azaz of Dictionopolis and the Mathemagician of Digitopolis kicked their sisters, Rhyme and Reason, out of the country – and it just hasn't been the same since. Milo decides it should be his mission to rescue these ladies. Why not?

After a very word-centric dinner in town (people in Dictionopolis eat their words… literally!), everyone bails and only Milo, Tock, and the Humbug are left with the king. After some deliberation, it is decided that the three of them will go on a journey to save Rhyme and Reason. But before completing their mission, they need to visit the Mathemagician to see if he'll give them the go ahead.

On their way to find brother number two in Digitopolis, they drive through the Lands Beyond and have a series of adventures: they meet a boy whose feet never touch the ground, a man who pretends he's multiple people, and a conductor whose orchestra injects color into the whole world. (Here's where we'll tell you, just go read it. It's just impossible to explain and quirkily as it happens.) Along the way, Milo learns that he needs to open his mind… quite a bit, in fact.

Next, the characters meet Dr. Dischord and the DYNNE, two individuals who are passionately interested in terrible sounds. From Dr. Dischord's home base, they travel into the Valley of Sound, where everything is silent. Through some tricky maneuvers, Milo manages to steal some sound and inject it back into the valley. He's just nailing it on this journey, huh?

After getting sidetracked when they jump to the Island of Conclusions, Milo, Tock, and the Humbug get closer to Digitopolis and run into the Dodecahedron. He accompanies them the rest of the way and shows them into a mine where numbers are brought out of the earth. They meet the Mathemagician, who explains the importance of numbers and just can't stop talking about math.

Using a bit of tricky logic, Milo gets the Mathemagician to grant them permission to move along toward Rhyme and Reason. They're almost there, but first, they have a few run-ins with some demons. Using the gifts he'd been given along his journey, Milo is able to help his gang make it to the Castle in the Air, where they meet Rhyme and Reason.

They all escape (in flight, thanks to the fact that time flies and Tock has a clock), and just in the nick of time, a huge army from the Kingdom of Wisdom comes to the rescue. The demons give up, and King Azaz and the Mathemagician welcome their sisters home. Hurray!

After a bit of celebration, Milo heads home. When he's back, he discovers that he was only gone for a couple of hours in his normal reality, even though he spent weeks in the Lands Beyond. Strange. The next day, the tollbooth's gone. But you know what? That's okay: by now Milo has opened himself up to the wonderful adventures and possibilities his own mind has to offer.

  • Chapter 1

    Milo

    • Our first chapter introduces Milo, who's a pretty grumpy guy. He's bored with his school and with life more generally: nothing's exciting or interesting. He has a lot of privileges, but they all seem kind of bland.
    • He uses his stroll home from a day of classes to think about how life kind of sucks. He seems pretty down in the dumps.
    • When he gets home, he goes to his room and feels like he has nothing to do.
    • But then he spots a mystery box in the corner of his room. It's a huge present, and he totally wasn't expecting anything of the kind. Awesome.
    • The box has his name on it, and there's a card attached: it says that inside the package are a tollbooth, signs, coins, a map, and a volume of traffic laws. Hmmm.
    • He opens the box and, sure enough, there's a tollbooth inside, but not all put together yet (kind of like something from Ikea).
    • Milo puts the contraption together and then displays the three signs. He consults the map and finds it sort of strange: it's very complete, but the countryside it describes is one he's never seen or heard of. Strange, indeed.
    • Oh well. He looks on the map and decides to travel to a place called Dictionopolis. He uses a toy car (it's large enough that he can sit in it), and heads through the tollbooth. Off he goes.
  • Chapter 2

    Beyond Expectations

    • So, Milo goes on his merry way. To his total shock, once he passes the tollbooth, he leaves his house and ends up on a road he's never seen before.
    • This kind of thing could freak out even the most well-balanced of us. Milo stays cool, though, and just decides to roll with it.
    • He passes through a beautiful area that he learns is called Expectations. He sees a sign that says if he sounds the car's horn, he can get some facts. That seems easy.
    • Milo immediately presses the horn and is introduced to a guy who calls himself the Whether Man.
    • Milo tries to ask whether he's going the correct way to get to Dictionopolis, and the Whether Man replies with a lot of nonsense about what it means to be on the "right road" versus the "wrong road" (2.9). Not super helpful.
    • The Whether Man says he definitely isn't the Weather Man, and tells Milo a little bit about Expectations. He's worried it will rain.
    • Milo makes his escape from this strange dude (and as he does, the Whether Man gets drenched by rain). As he drives, his mind wanders, and he ends up going down a path that perhaps he shouldn't have taken.
    • The pretty landscape fades away to repetitive boringness, and Milo feels like each little part of the road takes forever to cross. His little car loses speed until it halts.
    • A group of small people called the Lethargarians – who, like chameleons, blend almost entirely into their surroundings – tell Milo where he is. This part of the land is called the Doldrums.
    • The Lethargarians take turns talking in order to sloooooooooowly explain what it's like to live in the Doldrums. And boy, do we mean slowly.
    • They aren't "allowed to think in the Doldrums" (2.41). Sure enough, there's an official law about this that Milo sees in his "rule book" (2.42). Also in this not-so-awesome place, they can't find things funny. Shmoop is not a fan.
    • These slow-talkers have a very strict calendar of events each day, where they do different types of nothing that are all very strictly laid out. Yay for nothing!
    • Their attitude seems a little like Milo's was in Chapter 1, no? The Lethargarians encourage Milo to hang out with them, and he's strongly considering it.
    • But then, the watchdog shows up.
    • This isn't any old watchdog: he's an ordinary dog whose torso (body) is really an alarm clock. The Lethargarians are totally freaked out by this and they all run away.
    • The dog/clock scolds Milo and tells him how to get out of the Doldrums. The answer? He has to actively think.
    • Milo works on this, and when Milo's little car starts working again, the clock dog hitches a ride. They leave the Doldrums far behind. Whew.
  • Chapter 3

    Welcome to Dictionopolis

    • Milo and Tock drive along together. Milo wants to know why Tock is named Tock when the sound he makes is "tick." Hmm, good question.
    • Tock is overwhelmed by emotion and relays his life story. He had a brother who was named Tick and only made the sound "tock." Ironically, the reverse happened to him.
    • He also explains the concept of time as he understands it. Turns out his family business is protecting time.
    • Milo and Tock keep talking about time until they get to Dictionopolis, which is a beautiful city. Actually, it's the type of place you'd read about in a fairy tale.
    • When Milo and Tock roll up, a man is standing outside Dictionopolis, guarding it.
    • He welcomes them, saying that it's the market day. He wants to know their reason for approaching.
    • Hmm. Milo doesn't have one.
    • So, after some digging around (literally, digging into the ground) the guard finds a reason (it's an object that says "WHY NOT?") and gives it to Milo. This is like his free pass into the city. How cool is this place?
    • Once Milo and Tock get in, five gentlemen greet them. The men take turns saying the same thing in five different ways. Huh?
    • They also welcome Milo and Tock to Dictionopolis, and introduce themselves as the king's cabinet. All together, the five guys talk like a cross between a dictionary and a thesaurus. They define and act out their words constantly. Sounds complicated.
    • The cabinet members tell Milo about the importance of individual words: they say that words grow in Dictionopolis' forest, and they explain how words are used in the country.
    • These strange dudes also invite Milo and Tock to the Royal Banquet.
    • Then Milo and Tock go off to explore.
  • Chapter 4

    Confusion in the Market Place

    • Milo and Tock emerge into the word market, which is in full swing. Vendors are selling words as if they were fruits and vegetables.
    • There are all kinds of different words available, and Milo is totally overwhelmed.
    • At first, he thinks he should buy some words and picks out three really fancy ones. But they're way too expensive, so he puts 'em back.
    • Actually, Milo can't really buy any words, because he doesn't have any cash. He does have a small "coin," but that's for the tollbooth when he goes home. He should probably hang on to that one.
    • Milo and Tock still enjoy browsing, though, and they stop at a stand where you buy individual letters and create your own words.
    • Each letter has its own flavor. A's are really popular, like vanilla, but Z's aren't. (Just like in Scrabble!)
    • Milo would like to make words, but he just doesn't know how to start.
    • Cue the guy who does know how to make word: sure enough, the Spelling Bee shows up.
    • The Spelling Bee is, surprise surprise, an enormous bee that likes to spell. He can't go through a whole sentence without spelling at least one word.
    • Milo's kind of freaked out by him, because he doesn't really like bees, but the Spelling Bee calms him down and tries to demonstrate his knowledge.
    • Milo makes him spell "vegetable," which the Bee does. Nailed it.
    • The Bee has just started to tell his life story when he's interrupted by the Humbug, a giant bug.
    • It's immediately clear that the Bee and the Humbug do NOT get along.
    • The Bee says the Humbug is a big fat liar, and the Humbug strikes back by telling a puffed up story of his own family history.
    • The two yell at each other and then bust out fighting.
    • During the fight, all the word stands get knocked over. Milo falls on the Bee, and Tock gets squished in a big stack of letters. Oh my.
  • Chapter 5

    Short Shrift

    • After the fight, all the words are out of order. This means that everybody talks very strangely for a while.
    • The Spelling Bee bails.
    • In comes Dictionopolis' single police officer, Officer Shrift. He's short, which makes him "short shrift." (Get it? To give the "short shrift" to something means to blow it off or pretty much ignore it.)
    • The policeman analyzes everything, and as he's assessing the situation, the Humbug steps forward and accidentally blames it all on Milo. What the heck?!
    • Officer Shrift accuses Milo of several things, none of which are actually his fault. So uncool.
    • Milo tries to think on his feet, saying that as a policeman, Officer Shrift can't judge him or determine his punishment (that would be the job of a judge or a jury, right?). But Officer Shrift explains that he's got the power to do both those things.
    • The officer gives Milo a sentence ("I am" [5.23] – get it? It's a sentence) and also says he'll have to go to jail for 6,000,000 years. Wow.
    • Tock is caught up in everything and he'll have to go to jail, too. Officer Shrift drops them off at the slammer and tells them that they'll be locked up with a witch. Then he heads out.
    • Tock and Milo are understandably upset. Milo makes a vow to be better at English.
    • Finally, the witch, who's in the cell with them, introduces herself.
    • She's an elderly woman who doesn't appear all that scary: her name is Faintly Macabre. She explains she's a "Which," not the ordinary Halloween-style witch (spelled w-i-t-c-h) we were probably expecting.
    • She used to have an important job in Dictionopolis helping people decide which words were appropriate when.
    • Unfortunately, she got too full of herself and hoarded the words. She encouraged other people not to use them at all. Since Dictionopolis makes money from selling words, she nearly destroyed the country's economy.
    • Because of this, the king, who's one of her relatives, put her in jail for life, and let other people start deciding which words they wanted to use whenever they wanted. Freedom of speech!
    • She gives Milo and Tock each a snack – punctuation marks, which taste like candy.
    • Milo is inspired to free the Which, but she says that there's only one specific thing that will take care of that. Rhyme and Reason have to come back to Dictionopolis.
    • When Milo asks why, Faintly Macabre says it's a whole "story" (5.75). Read on, because she'll give them the lowdown in the next chapter.
  • Chapter 6

    Faintly Macabre's Story

    • This chapter begins with Faintly explaining what happened to Rhyme and Reason.
    • She starts out by giving the backstory, which involves a prince setting out on an exploration. He arrives in a complete wasteland and eventually conquers all the bad things living there. When he's done, he creates a city, called Wisdom.
    • At first, Wisdom is just a tiny part of the remaining wasteland. The prince, now a king, uses Wisdom as a base and gradually wins more and more territory.
    • The king's life flashes by, before he knows it, he has two sons.
    • The sons continue their dad's mission of gaining territory. They each found their own cities, Dictionopolis (we know that one) and Digitopolis. As you might have guessed, the first is for words and the second for numbers.
    • The two brothers each think that their city is the best and they quickly become rivals.
    • While this is going on, the king discovers two abandoned baby girls. He adopts them into the royal family and names them Rhyme and Reason. Cute.
    • After the king passes away, his sons, Azaz (Dictionopolis) and the Mathemagician (Digitopolis) share the kingship of Wisdom and are supposed to take care of baby sisters Rhyme and Reason.
    • For a while, it's all good, and Rhyme and Reason become famous for being fair and honest.
    • But the brothers can only get along for so long, and eventually they have the fight to end all fights. They want Rhyme and Reason to choose between "words and numbers" (6.20).
    • Rhyme and Reason end up finding a happy medium: they say that the two are equally important, but in different ways. Sounds fair to us.
    • But this pleases no one and the two sons send the two sisters away, to the Castle in the Air.
    • And that's where Faintly's story ends. The two sisters are still gone, and so all the realms suffer.
    • Milo still wants to save the day, but there's the little problem of his jail time.
    • But Faintly tells him that he and Tock can go any time. Officer Shrift won't be back to check on them, and he didn't lock the door. Oh, okay.
    • So Milo and Tock leave. That was easy.
    • As they're leaving, they run right into the cabinet members, who say they're late for the banquet.
    • The cabinet members take Milo and Tock for a ride in their "wagon" (6.54). This little contraption moves when people are silent because it "goes without saying" (6.56). Man, these puns are just too good to be true.
  • Chapter 7

    The Royal Banquet

    • The cabinet members bring Milo and Tock into the palace, which is beautiful.
    • Everyone from the market is there: the Humbug, the Spelling Bee, and Officer Shrift.
    • Officer Shrift doesn't seem to mind that Milo's left jail, and the Humbug tells Milo that he (Milo) will get to pick what everybody has to eat. Things change quickly in Dictionopolis, it seems.
    • King Azaz (remember him from Faintly's story?) comes in, and has everybody sit down. He asks Milo and Tock about themselves, and makes fun of Milo for not seeming to have any real entertaining skills. These guys are harsh!
    • Milo's in charge of what they eat, but isn't sure what to ask for. He thinks about how his mom is always telling him to be a good, polite guest.
    • So Milo orders a "light meal" (7.31). He means "light" as in snacks, not heavy courses, but the food that arrives is actually made of light. (Should have guessed!)
    • The Humbug and the king encourage Milo to try again, so he orders a "square meal" (7.35). But this time, the dishes that show up are a bunch of squares, which don't seem to taste very good.
    • Overall, Milo's done a pretty bad job of ordering food for everyone. We'll cut him some slack though, it seems like a complicated task.
    • The king then announces that everybody has to make a speech, and Milo has to go first. Milo's not really sure what to say, so he starts by greeting everyone.
    • The king cuts him off (how rude!) and then has each of the other guests make a speech. The Humbug starts and the king finishes. Each person makes a speech that's just a list of the foods they'd like to eat that night. Oh.
    • Milo realizes too late that his speech should really have been his dinner order. His food arrives and looks pretty gross compared to everyone else's.
    • The cabinet members try to console him with the breadbasket, but end up talking over each other too much and making the king mad.
    • When everybody's finished (Milo didn't have his), dessert is brought in. It's all "half-baked ideas" (7.75). (More puns!)
    • These are a big hit. Everybody else chows down, while Milo takes one "idea" (they're like cake) for the road.
  • Chapter 8

    The Humbug Volunteers

    • Everybody's stuffed.
    • This is especially true for the Humbug, who thinks he's made himself ill.
    • The king is about to tell them all something, but the majority of the people at the feast all run away. What is with these people?
    • The only ones left are the king, Milo, Tock, and the Humbug. The king is kind of bummed about this.
    • Apparently, the other people have all gone straight to their next meal.
    • It turns out that Dictionopolis has too many words and not enough sense. The king and the Humbug brainstorm, but none of the ideas sound good.
    • Milo brings up the whole Rhyme and Reason thing. Azaz says he'd like it if they'd come back, but that it'll never happen.
    • But wait: the Humbug jumps in and says he knows how it could happen. The princesses could come back if their saviors (Milo and Tock, obvi) could go to Digitopolis and get the Mathemagician's permission, and then go through a dangerous journey to rescue the princesses from the Castle in the Air.
    • Each part of the trip has its own specific danger. Milo thinks it's totally unsafe, while the king kind of seems to like it (well, duh, he doesn't have to go).
    • Before they know what's happened, Milo and Tock have been given the task of going on the trip and bringing back Rhyme and Reason.
    • The king warns them that they'll encounter at least one terrible obstacle, but he won't say what it is. Why not? We have no idea.
    • He gives an order and a bunch of servants come in. They tidy up after the banquet so well that the whole palace disappears. Just like that.
    • Azaz presents Milo and Tock with a box full of words. It's both a weapon and a protective device for them to use on their trip.
    • Then, the king says the Humbug will go with them to help. The Humbug is even more upset about having to go than Milo and Tock. Serves you right for volunteering them, Hummy!
    • They all bid each other good-bye, and then Milo, Tock, and the Humbug set off on their quest.
  • Chapter 9

    It's All in How You Look at Things

    • Milo, Tock, and the Humbug drive along. They're in uncharted territory, and the Humbug talks about "quests" (9.2).
    • As they drive, the landscape changes significantly. They see a sign that says they will be arriving at a "Point of View." Sounds nice to us.
    • They stop the car and meet a new person, a boy who's hovering in the air. The boy's feet are about as tall as Milo's head.
    • The boy says that things depend on how you look at them. He gives several examples, and then explains why he's so high up in the air. His whole family starts out at the height they're going to be. Then, as they get older, their heads stay at the same height while their feet grow closer to the ground. It's the opposite of how people like Milo see the world.
    • The boy, who is named Alec, explains that he can "see through things" (9.31). This is usually an advantage, but it means that often he can't see the things that are closest to him. He tells Milo, Tock, and the Humbug what each of them is thinking about.
    • Milo realizes that he could share Alec's viewpoint if he wanted to – this would make him reach the same height and dangle in the air, too – but this is too hardcore for him. He decides he'd rather stay as he is.
    • All four characters talk about the importance of having their own ways of looking at the world.
    • Alec emphasizes this by talking about how a certain amount of water could seem like a ton to a small animal and like practically nothing to a huge animal. Good point, Al.
    • Alec offers to show the others around. As they start the tour, Alec talks about the people who are upside down and "grow up toward the sky" (9.46). They can get into the heavens, according to the legends he knows.
  • Chapter 10

    A Colorful Symphony

    • The four musketeers – Milo, Tock, the Humbug, and Alec – run through the woods.
    • They are having a great ol' time until they lose their way (although Alec doesn't seem bothered by this anyway).
    • There's a nearby house, so they go up to ask its resident for directions.
    • Alec says the person who lives there is a giant, but the man who opens the door just looks like an average-sized person. He says he's a small giant and sends them to talk to the "midget."
    • When Milo and Tock get to the other end of the house, the person who opens the back door looks just like the "giant." He says he's a big midget, and then he refers them to the "fat man." On the third side of the house, the same man appears (this time, as the "fat" man) and refers Milo and Tock to the "thin man."
    • The thin man appears at the fourth door of the house. Guess what? It's still the same guy. But when Milo points this out, the giant/midget/fat/thin man asks him to keep it to himself. The man plays all these parts so he can feel special. Fair enough.
    • But the man can't tell Milo and Tock where they should go to get un-lost. He just tells them to go away.
    • (The Humbug has slept through all of this, by the way.)
    • Alec wakes the Humbug up and encourages them to keep going. Alec keeps playing tour guide and explains that most of the people that he knows live in a city, called Reality.
    • The group soon passes a beautiful city, but it's not Reality: it's another place called Illusions.
    • Alec takes a sec explains what illusions are. (If you're curious, go check it out and hear it from the source!)
    • Finally, the group gets to the city of Reality. But even though it's all around them, none of them can see it.
    • Alec dives right into Reality's history: it used to be visible, but because its residents never paid attention to it, it slowly slipped away. They didn't take the time to look at it, so it disappeared from sight. All the elements of the city are still there, but no one can see them. And it doesn't seem to matter.
    • Milo says that it's too bad Illusions and Reality can't be one city. Alec responds by saying that they could be one city if Rhyme and Reason came back. (These ladies sure are important, it seems.)
    • Next on the docket, Alec takes them to a musical performance.
    • There's a huge orchestra playing, but Milo can't hear anything. It turns out that the orchestra isn't playing traditional music. As they play, led by an excited conductor, they put different colors into the world: the group has just arrived in time to watch the orchestra play the sunset.
    • The conductor, Chroma, talks with Milo and shows him what would happen to the world if the orchestra didn't play anymore. All the colors of the entire globe would just fade out.
    • Everybody is really impressed. As they should be.
    • Chroma says he's tired and is going to take the night off. He puts Milo in charge and asks him to be an alarm for the next morning.
    • He takes off and everybody else snoozes.
  • Chapter 11

    Dischord and Dynne

    • Milo gets up at the perfect time to wake Chroma.
    • But he's so tempted by Chroma's job – it looks so cool – that he decides to have a go at it.
    • Things start off well, but conducting the sunrise is much harder than it looks. Things get out of control very quickly, and a whole week rushes by, full of all the wrong colors. Oops!
    • The chaos stops only when Milo stops conducting out of total exhaustion.
    • Chroma wakes up and starts a new day like nothing happened. And actually, nobody really knows except for Milo and the orchestra. Phew: crisis averted.
    • With that, Milo, Tock, and the Humbug have to be on their way. When they're saying goodbye, Alec gives Milo a special telescope, which will help him to see things better.
    • The three friends then drive quickly away. The road they find is much steeper and more difficult than previous ones. Uh oh.
    • Soon they come to a "carnival wagon" (11.29) that is decorated to advertise the business of Kakofonous A. Dischord, Doctor of Dissonance. (That's quite a mouthful!)
    • Milo wants to ask the doctor some questions about the route, but the person who greets them has his own agenda.
    • He asks a bunch of questions about strange noises they might have heard. But neither Milo, Tock, nor the Humbug has ever heard them.
    • The three travelers go into the wagon as the doctor keeps asking questions. They're all kind of freaked out but don't want to let their feelings show.
    • Dr. Dischord examines the three of them and says they need more noise in their lives. He begins concocting a mysterious potion that will "cure" their sickness. As he mixes it, he tells the three travelers about his business. He works on making noise and harsh sounds, rather than soft or nice ones. Interesting profession, that's for sure.
    • When Dr. Dischord explains what his cure will do – make sure the three hear bad things, not good ones – the travelers all refuse it. Good call, guys.
    • So, Dr. Dischord says he'll give it to the DYNNE, genie-like thing that appears from a bottle and is composed entirely of smoke.
    • Dr. Dischord tells the DYNNE's sad backstory: turns out, the DYNNE is responsible for most of the noise in the world.
    • A joke the Humbug makes upsets the DYNNE, who cries. Then he weeps some more at the fact that none of the three travelers seem to respect noise in the way that he and the doctor do.
    • Dr. Dischord cheers up the DYNNE by reminding him of all the important ways noise works in the world. Then, he tells the travelers they should get going: the DYNNE has his own path to travel for the day.
    • When the doctor and DYNNE find out where Milo, Tock, and the Humbug are going, they freak out: it's dangerous and frightening, they say. In order to get to Digitopolis, these three will have to "pass through the Valley of Sound" (11.99). For whatever reason, Dr. Dischord and DYNNE are totally scared of this place.
  • Chapter 12

    The Silent Valley

    • Milo, Tock, and the Humbug have gathered their courage and driven away from Dr. Dischord.
    • They know that they're about to get to the Valley of Sound, which should scare them, but so far things don't seem that bad. Deep breath.
    • After a few minutes, though, they figure out the problem. They've entered an area where there aren't any sounds.
    • They try to talk, but nothing happens. Their car doesn't make any noise, nor does the outside world. This is like a bad dream!
    • But they keep going and end up finding some people who have figured out how to communicate without sound. They use signs to show the three visitors what the problem is.
    • Here's the story: their leader, the Soundkeeper, took sound away from them.
    • They used to have all kinds of sounds, but didn't treat these sounds with enough respect. People paid less attention to good sounds and more attention to bad ones.
    • Eventually, Dr. Dischord and the DYNNE showed up, but they only made things worse instead of better.
    • So, the Soundkeeper kicked Dischord and DYNNE out, and then took all the sounds away. That means that the people who live in the Valley live in constant silence.
    • The people ask Milo for some help. If he can go into the Soundkeeper's fortress and bring out just one little noise, they will be able to win back the rest.
    • Milo's up for the challenge, so he goes into the fortress to meet the Soundkeeper. Immediately, he feels better, because within the fortress there are sounds. He's happy to be back somewhere more normal.
    • The Soundkeeper's a pretty weird lady. She values silence as much as the people outside her fortress are tired of it. At least, she says she does.
    • She helps Milo explore the collection of sounds in the fortress, explaining where sounds come from and how they are recorded for all time. She says that the sounds are saved in the fortress for the good of the world. They are all automatically categorized and put in order.
    • She explains what sounds look like. For example, each time you clap your hands you produce a piece of paper. Each of the sounds turns into a tiny object.
    • Milo thinks of various ways to take a sound outside the vault – like asking for one straight up, or trying to hide one in his pockets. But the Soundkeeper is wise to his ways and she doesn't let it happen.
    • At the end of their meeting, Milo asks why the Soundkeeper hides all the sounds. She says that she doesn't want to let them out because she can't control how they'll be used.
    • Milo is about to argue with her some more, but he stops: he realizes that he's holding the sound of the next word he was going to speak ("but") in his mouth.
    • He keeps his mouth shut and leaves.
  • Chapter 13

    Unfortunate Conclusions

    • Milo doesn't have much time: as soon as he talks, he'll lose his stolen word.
    • So he races back to the others. He writes down what he's done, and the people of the Silent Valley get ready to use his word as their weapon. They set up a big cannon, and Milo says his word into it.
    • Then, the Silent people fire their cannon at the Soundkeeper's fortress.
    • The "but" looks small, but as soon as it hits the fortress it does the trick. The fortress sort of explodes, and all the forbidden sounds come out at once.
    • For a while, as you might think, it's a complete cacophony (a mess of unmatching sounds). But the cacophony fades away remarkably quickly, and the citizens reabsorb their old sounds with what seems like no problem.
    • Then they all go about their own business. Man, everything happens really quickly in this book, huh?
    • Milo, Tock, the Humbug, and the Soundkeeper are left behind. The Soundkeeper is super sad, and the other three can't console her.
    • What cheers her up is the appearance of the DYNNE, who has gathered up some of the leftover noises. He doesn't think they're useful, because they aren't unpleasant, but the Soundkeeper is so happy to have them back.
    • She tries to give the DYNNE a present of nice sounds as a token of her thanks, but this freaks him out and he leaves (he only likes bad sounds, remember?).
    • It turns out the Soundkeeper also wishes Rhyme and Reason would come back. Everyone's on board, huh? She wants to help Milo in the quest, too, and so she gives him a little box of different sounds.
    • Then, she tells them which way to go to get to Digitopolis.
    • But the characters aren't so lucky as to get to their destination right away. While they're going along in their car, each of them makes a claim that isn't based in fact. As soon as they do, they vanish and reappear on an island in the middle of the Sea of Knowledge. This should be interesting.
    • On the island, they meet a man who says he doesn't know his own identity. The three want him to tell them where they all are, but he wants them to tell him who he is. He just keeps saying the things he "can be," so the other three decide is name is "Canby." Easy as pie.
    • In turn, Canby says that this island is called Conclusions and they have all "jumped" (13.54) there. (Take a second to bask in the glory of this play on words.)
    • Canby says that people get to the island all too easily: it's leaving the island that's hard. And, in fact, the island is terribly crowded.
    • To leave, Canby says, they have to swim back to land.
    • Milo and Tock force the Humbug to gear up for it, and the three of them sludge through the sea back to land. They've all learned a lesson from it (no more jumping to conclusions!). They get in the car and are off on their way again.
  • Chapter 14

    The Dodecahedron Leads the Way

    • The three travelers – Milo, Tock, and the Humbug – pass a road sign to Digitopolis. They're headed in the right direction!
    • The sign starts with the distance in miles and then goes down in increments all the way to half inches.
    • There are all kinds of ways to measure the distance to Digitopolis, and the travelers can't agree on which measurement they should use.
    • Someone shows up to help them: the Dodecahedron.
    • He's called the Dodecahedron because he is one. He has "twelve faces" (14.14). (A dodecahedron is a three dimensional thing with twelve flat sides).
    • The Dodecahedron explains some of Digitopolis' philosophies to the travelers, particularly Milo. Then he says he'll hop in their car with them and guide them, but only after forcing them to do a little math. (They're trying to figure out how long it will take for them to get from where they are to Digitopolis itself.)
    • Their new guide also tells them where numbers come from. They're like jewels buried deep in the earth, and they have to be brought out through a mining process.
    • To prove it, the Dodecahedron takes Milo, Tock, and the Humbug into a mine.
    • Here, they soon meet the Mathemagician, who helps further explain the numbers-focused philosophy of the realm. Here, numbers are more important than words. (In case you hadn't noticed.)
    • The miners think numbers are the most special things of all. Even though their mine produces what we humans would think of as very valuable objects, like precious stones, the people of Digitopolis don't see the value in them. They only see the value of the numbers.
    • In fact, the Mathemagician dismisses a huge pile of precious stones like they're trash. Instead, he turns his attention to something far more important: lunch.
  • Chapter 15

    This Way to Infinity

    • The characters all have lunch inside the mine.
    • Milo, Tock, and the Humbug are all super-hungry. So when they're done with their soup they have seconds – and then thirds, and so on.
    • The more they eat, the more they want to eat.
    • When the soup is taken away, they're even hungrier than they were to start with.
    • The Mathemagician explains that in Digitopolis, people only eat when they're full. It's the opposite of what Milo and the other two are used to. Once again, we have to look at things a little differently.
    • All the details about the way people in Digitopolis eat are really an excuse for a math lesson about negative numbers and zeros. We're onto you, Mathy.
    • Then, the Mathemagician helps them magically travel to his office, which he does by erasing everything with his magic wand (which is an enormous pencil).
    • Surprise surprise, The Mathemagician uses his wand to do more magic/math.
    • Then Milo has a few questions. He tries to ask what the biggest number ever is, but has a hard time explaining what he means. Tock steps in.
    • The Mathemagician answers that however large a number Milo can think of, there's always going to be one that's even bigger. The same is true for the tiniest number ever. There will always be one that's tinier – and on and on into infinity.
    • In fact, Infinity is a place, and the Mathemagician tells Milo how to get there. He can follow a line or go up some stairs.
    • Milo is too curious to resist, so he tries out the stairs, just to get a taste of Infinity.
  • Chapter 16

    A Very Dirty Bird

    • Milo climbs and climbs. But the higher he goes the more it seems like there's more to go. (We all know that feeling!)
    • Just as he's getting totally worn out, he runs into another little boy. The boy is only partly there, though. That is, he's only there on one side.
    • The boy explains he's ".58" of a child. Then he tells Milo about the importance of fractions and percents – he's like the poster child of an "average" (16.14).
    • Milo's confused by their conversation (so is Shmoop) and feels more ignorant than ever.
    • The little boy tries to give Milo advice about learning, and Milo decides to return to his friends – and abandon the idea of trying to reach Infinity. Good call.
    • When he gets back to the others, he complains to the Mathemagician about how thinking is tough and how finding the right answer can be so hard.
    • This is the perfect opening for the Mathemagician to talk about how much Rhyme and Reason are missed.
    • The Mathemagician blames his brother, King Azaz, for this. He tells Milo about how hard it is for the two brothers to communicate.
    • The travelers try to get the Mathemagician's approval to rescue the princesses, but he says he can't give it because Azaz agreed to it already (and he sure can't agree with his brother).
    • Milo uses logic to fool the Mathemagician into giving approval.
    • The Mathemagician lets them go, but with two warnings. One is about the demons that will attack them once they get closer to the princesses. The other, he says, he can only reveal once they get back.
    • The Dodecahedron shows up and hands Milo the important presents that he (Milo) has collected along the way. The Mathemagician also contributes a gift: a magic wand that looks just like his, only smaller.
    • To keep going, Milo, Tock, and the Humbug have to proceed on foot. So they do. They say goodbye to the Mathemagician and the Dodecahedron and plunge right into the dangerous nearby mountains, leaving Wisdom and moving into Ignorance.
    • The farther they go, the more depressing it is.
    • When they've made it pretty far, and decide to rest for the night, they run into a mean and talkative bird. Every time they try to talk to it, the bird twists all of their words around. They can't even finish a sentence without it interrupting them and shifting their meaning.
    • The bird says he's named the Everpresent Wordsnatcher, and that he's from Context.
    • Milo accidentally hurts the bird's feelings when he asks if it's a demon (answer: no), and so it takes off.
    • The three others keep going, and soon they meet a nice-looking man. He's wearing snappy clothes but has no features in his face. The man is super-nice to them and asks if they'll do him a favor.
    • Milo, Tock, and the Humbug are happy to oblige. Maybe they were too kind: the man gives each of them a painstaking, time-consuming task.
    • The three get started on their tasks and then just keep going… and going…
  • Chapter 17

    Unwelcoming Committee

    • Eventually, the three workers – Milo, Tock, and the Humbug – realize that they've been working for what seems like forever and, well, nothing's happened.
    • Tock tells Milo to use the wand the Mathemagician gave him to determine how long their tasks will take.
    • Milo does some quick thinking and realizes that it will take hundreds of years. That's no good.
    • When he questions the man about it, the man tells them that they should do "unimportant things" (17.14) instead of important ones. It sounds like he's made that his life's work.
    • Milo realizes the nice-seeming man is actually a horrible demon: the Terrible Trivium.
    • The three travelers feel trapped.
    • Things get worse and worse as the Trivium tells them more of his philosophy and it seems like they will never be able to escape.
    • Then they hear a voice yelling for them to get out. Each of them thinks it's one of the others – oops – and they all obey.
    • They run and run… and run. Trivium is chasing them, but they leave him behind when they start pushing through something that feels like quicksand.
    • All three of them continue to follow the bodiless voice and then – ouch! – they all fall down into a huge hole.
    • From there, they hear the voice threatening them. The voice describes itself as a terrible and scary demon, but Milo uses one of the presents he was given – the telescope – to take a good look at it.
    • Milo figures out that the huge demon is just a tiny little thing: he's not scared of no tiny demon.
    • The demon presents himself as "the demon of insincerity" (17.43), and he's so upset by being discovered for what he really is that he leaves crying.
    • Milo, Tock, and the Humbug work together to climb out of the pit. It takes quite a while, but they manage it in the end.
    • At that point, the Humbug takes the lead and, well, he walks them right into the hand of a giant.
    • The giant is clearly about to eat them, so Milo tries to keep himself and his friends alive by starting a conversation with the guy. After all, as long as the giant's talking, he can't eat them. Smart move, Milo.
    • The more they talk, the weirder the giant starts to feel. It turns out that he doesn't like thoughts.
    • Milo shows him the box of words from King Azaz. Just the thought of them makes the giant sick, and he releases his prisoners.
    • Unfortunately, as soon as he does this, he goes and tells all the other demons about Milo, Tock, and the Humbug. Different types of demons emerge from all over, and they all start coming toward the three travelers.
    • Our three friends have no choice but to make a run for it.
  • Chapter 18

    Castle in the Air

    • Milo, Tock, and the Humbug go up the mountain as fast as they can. Meanwhile, the demons are following them.
    • At last, they find the Castle in the Air, but a man sitting in front of the entrance makes them stop.
    • The man, who introduces himself as the Senses Taker (like a census taker… how about that?), asks them a bunch of questions and says they have to answer them all before they can get through. As soon as they've finished, he asks a bunch more questions. Come on, dude!
    • Even though the demons are getting closer, the man insists that these three travelers answer his questions.
    • Finally they finish, but the guard tries to discourage them from going in the Castle. Instead, he provides each of them with the fantasy they'd like best.
    • Milo, Tock, and the Humbug are each mesmerized by their own fantasy, and they forget all about the danger they're in. (Hmm, it seems like the Senses Taker has taken their senses!) Meanwhile, the demons get even closer.
    • In the end, being distracted is what saves them. Milo is so into his fantasy that he can't even hold on to the gifts he was carrying. When he drops them, the box the Soundkeeper gave him falls apart and all the little sounds come out. They're enough of a new distraction that all the Senses Taker's fantasies fade away.
    • The Senses Taker still seems pretty scary and says that the only way they will be able to defend themselves against him, ultimately, is by laughing. Laughing?
    • Well, the other demons are about to overtake them, and the Humbug, Tock, and Milo run over the Senses Taker in their haste to climb the last stairs to the Castle in the Air.
    • The stairs are scary, but they prevail, and make it to the Castle at last. Whew.
    • Two beautiful women welcome the travelers. Milo recognizes them: Rhyme and Reason.
    • The travelers explain their mission, and the princesses say they should take a few minutes to relax before they try to battle their way out of the castle.
    • Milo has some private time with the princesses, who give him some wise ideas about how to approach education – and life, really. They say he shouldn't be afraid of not being right all the time.
    • Their conversation is interrupted, though, when all the demons attack the castle from below and separate it from the stairs. The castle starts floating away.
    • So the good guys smartly decide it's time to be on their way.
    • Because "time flies" (18.72), Tock is able to fly through the air, and all the others grasp on to him.
    • They abandon the castle and head for home.
  • Chapter 19

    The Return of Rhyme and Reason

    • Tock can't keep them all in the air for too long, but he manages to get them past the demons – at least, temporarily.
    • He, the Humbug, Milo, Rhyme, and Reason hit the ground and keep moving. Rhyme and Reason get to ride on Tock (which tells you how big of a dog he is), while Milo and the Humbug have to fend for themselves.
    • The demons are right behind them, and there are a bunch of creepy ones that our heroes are just now seeing for the first time: the Triple Demons of Compromise, the Horrible Hopping Hindsight, the Gorgons of Hate and Malice, the Overbearing Know-it-All, the Gross Exaggeration, and the Threadbare Excuse.
    • The heroes get closer and closer to the border between Wisdom and Ignorance (when they get to Wisdom they'll be safe), but the demons are catching up to them. The Giant and the Trivium are following them, along with another one called the Dilemma.
    • The demons are about to swallow the heroes alive, when saviors emerge. In the nick of time, a huge army from Wisdom appears. All the people and things Milo encountered along the way are represented, with King Azaz and the Mathemagician in the lead.
    • After seeing the army, all the demons give up and retreat. Victory!
    • King Azaz's cabinet comes forward and congratulates the returning heroes. Rhyme and Reason are welcomed home, and their rescuers are praised.
    • To celebrate, they all begin three days of partying. It starts with a huge parade.
    • During the parade, the travelers are horrified to learn that the one thing that neither King Azaz nor the Mathemagician wanted to say was that their quest was "completely impossible" (19.54). It's only because they didn't know it was impossible that they could attempt it. How about that?
    • At a neutral point in Wisdom, the parade halts for the three days of partying. All the (nice) characters we met during the book show up to jam. There's eating and drinking and speeches.
    • King Azaz and the Mathemagician seem like they've really made up.
    • The princesses tell Milo he has to be on his way: it's sad but true. He has to say goodbye to everyone, even Tock and the Humbug.
    • Milo gets his car back, and he takes off. As he's leaving, he hears the Mathemagician and King Azaz start to squabble once again over language and math. Oh my.
  • Chapter 20

    Good-by and Hello

    • Milo drives home. On his way, he realizes that that he's been gone for ages, which is probably not so cool with his parents.
    • Yet, by the time he gets home, he discovers that it's only been a few hours back in human time. He hasn't even missed dinner.
    • He's wiped out, so he eats and goes straight to bed.
    • After school the next day, he's really excited to go home, go through the Tollbooth, and start another adventure.
    • But the Tollbooth's gone. All that's left is a little note, which says he doesn't need the Tollbooth anymore. It says that he now has the power to make his own adventures.
    • At first, Milo is really upset: he won't ever get see the friends he made in the Lands Beyond. But he's more excited to be in his own world than he ever was before.
    • This guy is ready to make his own adventures.