After Hurricane Donna has safely subsided, Steinbeck has second thoughts about his trip. He feels attached to the comforts of home and his wife’s companionship, and he’s anxious about leaving them for months. He considers his illness and advancing age but decides he can’t allow himself to become a “baby,” a fate to which he believes many old men succumb. He says a quick goodbye to his wife, loads Charley into Rosinante, and embarks on his adventure. To avoid the New York City traffic, he takes ferries from Long Island to Connecticut. On one of these boats, he meets a man who works on a submarine. They converse over coffee. The man seems content with his job, but Steinbeck expresses fear over the stealthy nature and nuclear technology of submarines—and the lonely isolation of those who work on them.

Steinbeck avoids spending too much time in Connecticut; he wants to avoid difficult city driving and doesn’t feel a need to explore areas he already knows well. His first stop is his son’s high school in Western Massachusetts, where students surround the truck hoping to hitch a ride. After a quick visit, he makes his way north into Vermont and New Hampshire.