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A very bored boy named Milo doesn't have anything to do with his life and believes everything is a waste of time. He gets home to find a box that includes parts to build a tollbooth with. After constructing it, Milo drives through the tollbooth in his toy car, heading for Dictionopolis.
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Milo shows up in the land of Wisdom, and starts his journey in Expectations. There he meets the Whether Man, who explains you have to go to Expectations first, before you can ever go beyond Expectations. Milo continues, and winds up in the Doldrums because he wasn't paying attention. He gets out thanks to a watchdog named Tock, who encourages him to think in order to get his car moving. Tock is now with Milo on his journey.
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Milo, now accompanied by Tock, continues his drive through the Foothills of Confusion and to the gates of Dictionopolis. They meet the king's advisers and are told that its Market Day in the city. The pair find themselves perusing the word market, where all the words in the world can be found.
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They meet some literary insects (called the Spelling Bee and the Humbug) in the marketplace. These two get into a big argument over how important words are, and destroy practically the entire word market by toppling into the various booths during their tussle.
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Milo and Tock get arrested by Officer Shrift for the destruction of the marketplace caused by the Humbug and the Bee. They're sentenced to 6 million years in the dungeon, where they meet the Which named Faintly Macabre.
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Milo and Tock are told about the creation of Wisdom by a king and his people's bravely driving away the evil creatures that once lived there. The king's sons, Azaz and the Mathemagician, argued over whether numbers or words were more important. When they asked princesses Rhyme and Reason this question, they said they were both equally important, and have since been banished to the Castle in the Air. Their return would solve pretty much any problem that now exists within Wisdom.
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A chapter of the book filled with puns, Milo and Tock, along with everyone else in the city, partake in a banquet in which you literally eat your words. For dessert they get half-baked ideas, and then all the other guests, except the Humbug, leave for dinner.
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Milo asks King Azaz if Rhyme and Reason can return to Wisdom, and the Humbug naturally suggests that Milo and Tock should undertake this quest themselves. The King agrees, also making the Humbug go. He gives Milo a box of all the words he knows, ands sends them on their way.
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The trio of adventurers start their way towards Digitopolis, and the first place on the way is the Forest of Sight. Following the road that winds through the forest, they come to Point of View. Here they meet Alec Bings, a kid who grows down, and are told of perspective.
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They get led around the Forest of Sight by Alec. They meet the Giant/Midget/Fat man/Thin man, see the cities of Illusions and Reality, and eventually met Chroma the Great, conductor of the symphony orchestra of color, whichs plays color instead of sound, and colors the world at all times.
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Instead of getting Chroma up to conduct the orchestra, Milo gives it a go himself. He winds up sending the whole world a week forward in time and misplacing all the colors of everything before quitting. Luckily, Chroma was still asleep. They move on and meet Dr. Dischord and the terrible Dynne, who capture and create all sorts of awful sounds. They hate any decent sound, including silence.
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They drive on, and pass into the Valley of Sound, which at this point, is actually silent. This is because the Soundkeeper didn't like how sounds were being treated, and kept them safe in her fortress, banning sound from the Valley for good. Milo goes and tries to steal a sound from the fortress that could be used as ammo to destroy the fortress and release the sounds. He manages to keep the 'but' that was on the tip of his tongue and smuggle it out of the fortress in his mouth.
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Once the 'but' is loaded into a cannon and shot off, destroying the sound fortress in a sound explosion, every sound is released back into the valley. The Soundkeeper knows she was wrong to keep the sound and wishes the princesses were back. Since Milo is going to save them, she gives him a gift of sounds in her support. They drive on, only to soon get yanked out of the car and shot toward the Island of Conclusions. They swim through the Sea of Knowledge and get back to shore, back on course.
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The group finally makes it to Digitopolis, led there the remaining distance of their travel by, as the chapter title suggests, the Dodecahedron, a man-like creature with 12 faces on his head. Once there, the first place they go is the Number Mine, where all the numbers in the world come from. Here is where they first meet the Mathemagician, in all his numerical glory.
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They are treated to some subtraction soup, which makes you hungrier as you eat it, then are shown by the Mathemagician the abilities a pencil has to offer. He continues to talk about numbers, and how they never end, then tells him all the smallest ones and largerst ones are kept in Infinity. Milo enters the way to Infinity eagerly.
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Milo realizes he's never going to reach Infinity, and returns to his friends after meeting .58 of a kid. The Mathemagician gives him some gifts, and they continue to the Mountains of Ignorance. The very first thing they meet here is the Everpresent Wordsnatcher, a bird who is usually out of Context. The first real demon they meet, the Terrible Trivium, gives them tasks that seem pointless and time consuming; they agree to do them and get to work.
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Milo uses his gifts to get he and his companions out of the messes the demons get them into. In order, he uses his pencil to do the math and figure out that their assigned tasks would take too long, his telescope to see that the Demon of Insincerity isn't all that scary, and his ideas to make the Gelatinous Giant lose his appetite. They're then chased by the demons of the mountains.
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They see the castle that the princesses are being held at, but are stopped short by the Senses Taker, who makes them see whatever they want to see, smell what they want to see, and hear what they want to hear. Milo snaps out of it though, and they all meet the princesses inside. They explain lessons to Milo about what all his travels should mean to him, then leave via flying over the demons on Tock, right in the knick of time. They aren't finished yet though.
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The demons continue to give chase, but are stopped by the armies of the entire Kingdom of Wisdom and sent back to the mountains in fear. Tock, the Humbug, and most importantly, Milo, are all hailed as heroes and peace is restored to Wisdom. Sadly, Milo has to return home.
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Milo gets home worried about how much time had passed, but he hadn't been gone that long. He goes to bed, goes to school, and gets back home the next day, all in the excitement of trying to figure out one thing- what fun thing he would do next!
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