- Now we learn about Steinbeck's interactions with truckers and his impressions of them and their lifestyle, as a group. We also get his thoughts on highways and driving, and the impact of both on how we think and daydream.
- Also, he reflects on the increasing popularity of mobile homes and considers whether that popularity relates to changes in the American lifestyle and priorities or is just part of the human inclination to wander.
- As he drove through the Midwest, he reflected on how it had changed since he was last there.
- As he recalls this, he also reflects on how regional dialects in general are disappearing, thanks to mass media.
- As Steinbeck stopped somewhere along his route (somewhere in the Midwest), a man came to harass him about trespassing. However, Steinbeck was so friendly in response that it completely disarmed this dude (whom Steinbeck called "the guardian"). Steinbeck and the guardian ended up enjoying some beverages together, and the guardian allowed him to stay after all.
- He and the guardian ended up going fishing together the next day, and they discussed the guardian's life.
- The guardian offered to let him stay longer, but Steinbeck was on his way to go see his wife in Chicago, so he peaced out.
- When he got to Chicago, he sent Charley off to a kennel-grooming place (much to Charley's displeasure) and tried to check into his hotel. However, since it was super-early in the morning (Steinbeck had traveled early to avoid city traffic), he wasn't able to get his room right away.
- Luckily for him, he looked like such a mess from his travels that the hotel management wasn't excited about having him waiting in the lobby for several hours. So, they let him into the room of someone who had just checked out for an early flight so he could at least shower and crash until his real room was ready.
- Once in his temporary room, Steinbeck was immediately preoccupied by all the stuff the previous occupant had left behind and built a story about him based on what he found. He called the occupant "Harry"—and really, built quite an elaborate tale about him (and his guest/mistress, "Lucille").