Chapter 1, Milo
• Milo is a boy who is always bored and always wishes he were somewhere else.
• One day Milo arrives home to discover a large box in his bedroom and finds when he assembles it that it's a large purple tollbooth.
• Milo chooses his destination by closing his eyes and pointing at the map, then dusts off his car, pays the toll and drives through with the intention of going to Dictionopolis.
Chapter 2, Beyond Expectations
• Milo arrives in Expectations, where he's greeted by the Whether Man who ushers Milo on his way.
• Milo fails to pay attention, takes a wrong turn and ends up in the Doldrums where he meets the Lethargarians.
• He soon meets Tock, the watchdog, who chastises Milo for killing time.
• Under Tock's guidance, Milo realizes that he needs to think in order to get out of the Doldrums, and he does.
Chapter 3, Welcome to Dictionopolis
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