Milo is in a slump where everything in his life seems boring and drab. When he discovers a mysterious tollbooth in his room, he drives through it, figuring he has nothing better to do. This simple action sets him on a path through the lands of Expectations and the Doldrums, into Dictionopolis, where all the world's words originate. Here Milo learns of the disappearance of Rhyme and Reason, the daughters of the King of Wisdom, and decides to try and rescue them. This mission leads Milo and his companions (Tock, a watch-dog who is part-clock and a disagreeable insect called the Humbug) to other strange places, including Digitopolis, a land entirely ruled by numbers, and the Island of Conclusions, on which one can only arrive by jumping.
I enjoyed the sense of humor of this book very much. I am a big fan of playing with the English language and Norton Juster uses a lot of fun puns and other clever turns of phrase that require a little bit of sophistication to understand. Kids love to feel smart, and this book gives them many opportunities to experience that feeling. So much of the story is clearly an allegorical commentary on the human condition and the problems of society, which kids may or may not realize, but which amused me as an adult. Because of these deeper threads running through the book, it is very clear to me why so many grown-ups sing its praises and eagerly read it with their own children.
I feel like there was a probably a critical window of time during my childhood (age 9 or 10, possibly) when I would have read this book and fallen in love with it. I'm a little bit sad to have missed that window, because I just don't feel that strongly for the book, even though I liked it a lot from a critical standpoint. I hope my own kids will have a stronger connection with it, so that they are the ones gushing to librarians about how great it is when they have kids of their own.