Our Phantom Tollbooth First Read Kicks Off: Chapters One and Two

by Tom B.

The Annotated Phantom Tollbooth

Perfect for Tollbooth obsessives…

Back on September 20th, we celebrated Building a Library’s first anniversary and announced that, the following week, I was finally going to start reading The Phantom Tollbooth – the book that inspired this blog – to my almost six-year-old daughter. And then… I took the following week off. Anti-climatic, I know, but it was a crazy week with swim classes and TWO soccer games and I was exhausted and blocked and I apologize. But, now that all my excuses are out on the table, I DID start reading The Phantom Tollbooth with my daughter last week and, so far, it’s been a pretty positive experience.

Let me state up front that I was a little worried that my daughter was too young for The Phantom Tollbooth. Norton Juster expertly plays with language and various abstract concepts throughout the book and I was concerned that aspects of the text would go over her head. As far as I can remember, I probably first encountered The Phantom Tollbooth when I was eight or nine, so I will admit that I am (still) concerned that I might be trying to introduce the novel to my daughter at too early an age. But, regardless of those concerns, I wanted to give Phantom Tollbooth a shot in our coveted bedtime reading slot last week and I’m going to periodically give updates on how the reading is going so far.

I’m calling this series “Phantom Tollbooth: First Read” and I’m planning to structure the updates in a similar style to the re-read or rewatch series that you can find on Tor.com or The Onion‘s AV Club. For those unfamiliar, in those series, the websites pick a book or a movie and a person episodically blogs their reaction to revisiting those works. For example, the blogger might post their ongoing reaction to rewatching all three seasons of Arrested Development or re-reading Stephen King’s Dark Tower books, chapter-by-chapter.

For Phantom Tollbooth, I’m going to adopt a chapter-by-chapter model, although some nights, we’ll be reading multiple chapters. For our first week, we started slow, only making it through the first four chapters. In the future, we may be moving through the book at a different pace, largely determined by what we’ve got going on that week. (Fair Warning: A trip to NYC will limit our progress this weekend.) I’ll give a quick summary of the chapter, my thoughts, my daughter’s reactions, and I might even toss in a few pieces of trivia from Leonard S. Marcus’ fantastic The Annotated Phantom Tollbooth as well.

Are we all set? Excuses made and plans delineated? Great. And, with that, let us begin…

THE PHANTOM TOLLBOOTH FIRST READ: CHAPTERS 1 AND 2 – “Milo” and “Beyond Expectations”


“I do hope this is an interesting game, otherwise the afternoon will be so terribly dull.” – Milo, The Phantom Tollbooth

The Phantom Tollbooth, Chapter One

Santa got my letter!

The opening passages of The Phantom Tollbooth were what sold me on the book as a kid. In a few short paragraphs, Norton Juster wonderfully captures the itchy, nagging boredom that can easily consume a child in the wrong frame of mind. I love comedian Louis C.K.’s inspired riff on how “Everything’s Amazing and Nobody’s Happy” and it shares some nice thematic parallels to initial mindset of Milo, the protagonist of The Phantom Tollbooth. To quote Juster:

There once was a boy named Milo who didn’t know what to do with himself – not just sometimes, but always.

When he was in school he longed to be out, and when he was out he longed to be in. On the way he thought about coming home, and coming home he thought about going. Wherever he was he wished he were somewhere else, and when he got there he wondered why he’s bothered. Nothing really interested him – least of all the things that should have.

It’s an incredibly powerful opening and, after reading into it a few paragraphs, I turned to my daughter and asked, “Do you ever feel like that?” “Yes,” she replied. “I get bored a lot.”

Milo rushes home from school – “for while he was never anxious to be where he was going, he liked to get there as quickly as possible” – and flops into a chair, consumed with the awful future of spending another boring afternoon with his boring books and his boring toys and nothing particularly interesting to do. At that moment, Milo notices a large package in his room, a box addressed simply “FOR MILO, WHO HAS PLENTY OF TIME.”

The Phantom Tollbooth, Chapter One

My daughter seriously covets Milo’s car…

Inside the box, Milo finds “ONE GENUINE TURNPIKE TOLLBOOTH” with instructions for its assembly and use. It also comes with three coins for paying tolls, precautionary signs, a map of the lands beyond (“up to date and carefully drawn by master cartographers, depicting natural and man-made features”), and a book of rules and traffic regulations.

Our family frequently travels across the country by car – we’re professional road-trippers – so, fortunately, I didn’t have to explain to my daughter what exactly a “tollbooth” was. After Milo opened the box, my daughter asked “That’s like in Ohio when they make you pay money to use the road and there’s the change bucket and the arm, right?” “Yes,” I replied. “Just like that.” “OK…”

Milo assembles the tollbooth and, “since, at the time, there was nothing else he wanted to play with,” he sets everything up, dusts off his small electric toy car, and prepares to make his way through the tollbooth. He randomly pokes his finger at the map in search of a destination – “Dictionopolis… Oh, well, I might as well go there as anywhere” – deposits his coin, and drives off in his toy car through the tollbooth.

We stopped at the end of this chapter and I asked my daughter for her opinions so far. I told her I was writing about this for my blog, so she told me to “write all this down.”

In her own words:

“I like it. It’s a very good book. I am worried that it will be boring, but I like that he’s going to have an adventure. He’s going to have an adventure, right, Dad? (Dad nods head.) Good. I wish I had a car like that. Who left him the tollbooth? Do they ever tell you? And Dictionopolis – I know that’s supposed to sound like “dictionary,” so I bet there will be a lot of words, maybe like in WordWorld. (For those unfamiliar, WordWorld is a PBS Kids show for preschoolers about a barnyard filled with characters physically constructed out of words – for example, the bear’s head is the letter “B” and her feet are the letter “R”, etc.)

When I said “Let’s move on to chapter 2,” she nodded and said, “Right. To the adventure.”


“What a strange thing to have happen.” – Milo, The Phantom Tollbooth

The Phantom Tollbooth, Chapter Two

I don’t think that toll money is being used for any noticable road-improvement projects on this stretch of highway…

Chapter Two opens with Milo surprised to find himself speeding down an “unfamiliar country highway.” (“Is he in Narnia, Dad?” my daughter asked, having never read the Narnia books nor seen the Narnia movies. “No,” I answered. “But good guess.”) Milo comments about how this game is “much more serious than I thought” and seems happy for the change of pace. He stops next to a small house with a sign that reads: “WELCOME TO EXPECTATIONS. INFORMATION, PREDICTIONS, AND ADVICE CHEERFULLY OFFERED. PARK HERE AND BLOW HORN.”

Milo honks and out runs the Whether Man, a jolly person with the unfortunate habit of repeating himself over and over again. I will admit – the arrival of the Whether Man marked our first stumbling block while reading. For whatever reason, my daughter took an instant dislike to the character, even though he’s only around for a few pages. Milo, at first, thought he was the “Weather Man”, and so did my daughter, but, as I tried to explain what he meant by “WHETHER” – “You know, like whether or not” – my daughter crunched up her nose and said, “I don’t like it. It’s confusing.”

I tried to explain, “Well, they’re playing around with the meanings of words. Like, isn’t it funny to go to a place actually called EXPECTATIONS right before you get to the place you want to go?” She shot me a dark look in response. “I guess.” At this point, I apparently looked dejected and my daughter grabbed my hand and said, “But I’m still really liking it, Daddy,” which was both incredibly sweet and a little pathetic. She can tell that I REALLY want her to like this book and she’s trying to protect my feelings. Again, that’s adorable, but it’s insane for me to put that kind of baggage onto a kid. That’s like a guaranteed way for me to ensure that she won’t enjoy The Phantom Tollbooth.

The Phantom Tollbooth, Chapter 2

Enter Tock the Watchdog, looking annoyed…

So my new mission is to be as nonchalant as possible about reading Phantom Tollbooth with my daughter. If she wants to read it, great. If not, no big deal. I just need to get her to stop thinking that I have a vested interest in her enjoying this book. (Even though I do.)

OK, let’s leave parental paranoia behind and get back to the story, Milo eventually leaves the Whether Man, commenting that, “It’s all very well to spend time in Expectations, but talking to that strange man all day would certainly get me nowhere.” As Milo drives away from Expectations, he soon becomes bored and distracted, and finds himself wandering into an increasingly gray and monotone landscape. His car slows down until it can move no longer and Milo discovers that he’s found his way into the Doldrums, “where nothing ever happens and nothing ever changes.”

In the Doldrums, Milo meets the Lethargarians, who explain to the young boy how completely exhausting it can be to do nothing all day. As they laboriously break down their daily schedule of loafing, lounging, and dillydallying, Milo finds himself yawning and falling in step with their boredom – that is, until the arrival of the Watchdog. The Watchdog (later known as Tock) is reviled by the Lethargarians because “He’s always sniffing around to see that nobody wastes time.” When the Watchdog finally appears, he angrily chases off the Lethargarians and confronts Milo with “What are you doing here?”

The Phantom Tollbooth, Chapter 2

Tock REALLY doesn’t look that pleased with Milo on the cover…

(At this point, my daughter said, “That dog is mad. Look at him in that picture. I thought he and Milo were friends. They’re friends on the cover of the book.” I then pointed that that Tock doesn’t exactly look particularly pleased with Milo on the cover of The Phantom Tollbooth, but quickly added, “OK, you’re right, they become friends later – just wait.”)

After the Watchdog recoils at Milo’s suggestion that he’s just “killing time,” he further bristles at Milo’s request for help to find the way to Dictionopolis. “Help you! You must help yourself,” the Watchdog argues.

Next comes one of my favorite exchanges in the whole book:

“I suppose you know why you got stuck [in the Doldroms].”

“I guess I just wasn’t thinking,” said Milo.

“PRECISELY,” shouted the dog as his alarm went off again. “Now you know what you must do.”

“I’m afraid I don’t,” admitted Milo, feeling quite stupid.

“Well,” continued the watchdog impatiently, “since you got here by not thinking, it seems reasonable to expect that, in order to get out, you must start thinking.”

And, with that, Milo starts thinking, his car starts moving again, and the Watchdog hops into the passenger seat, asking, “Do you mind if I get in? I love automobile rides.”

(That line made my daughter laugh out loud.)

So Milo and the Watchdog get back on the road, headed towards Dictionopolis and Chapter Three.

Again, I stopped my daughter and asked her what she thought after Chapter Two. In her words:

“It’s confusing sometimes. I really got confused by the Whether Man. I don’t get what you mean by a ‘whether or not’ man. But I liked the Doldroms, that was just people being bored, and I liked the Watchdog. I think it’s cool that thinking makes his car move.”

So, that’s us done reading chapters one and two of The Phantom Tollbooth. I’ll try to post my daughter’s reaction to chapter three soon – as a preview, just know that there’s a moment in chapter three that made my kid say out loud, “OH! So THAT’s what the book is about!” Hope this isn’t too painful to follow along with. If you have your own memories of reading The Phantom Tollbooth, please feel free to share them in the comments section below.


With every installment of “Phantom Tollbooth: First Read“, I’m going to end with my favorite nugget of information related to each chapter gleaned from Leonard Marcus’ terrific annotated edition of The Phantom Tollbooth. Here goes:


Referring to the assembly instructions for the tollbooth on page 7, specifically the line “easily assembled at home.”

  • Juster recalled: “When I was a child, almost all presents, it seemed, came in pieces and had to be put together. Some I loved, like erector sets and model airplanes. In fact, I think I learned to read well, and carefully, by poring over the directions for putting together model airplanes. … To me any real present required participation and patience” (N.J., Notes I, p. 4).


Referring to the moment when the Watchdog jumps into the car with Milo at the end of the chapter.

  • Maurice Sendak singled out this scene as a favorite: “You know you’re in excellent hands when, in the midst of some nutty, didactic dialogue, the author disarms you. … It’s what Tock, the literal watchdog … says next that makes my heart melt, as it did on my very first reading way back when: ‘Do you mind if I get in? I love automobile rides.’ There is the teeming-brained Norton Juster touching just the right note at just the right moment” (“An Appreciation,” by M.S. for the 35th-anniversary U.S. edition, 1996).

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