On the bus to New York, Dicey finds herself contemplating the concept of home. She realizes that she has long since given up the hope of finding home, and instead is merely looking for a place where she and her siblings can stay and be themselves. She realized that they were not free at Eunice's, as they had to expend energy and time feeling grateful for Eunice's sacrifices.
Dicey looks down at Maybeth, who appears tense, and tells her that they may have to go back to Eunice's, and Maybeth nods. They arrive in New York City, and negotiate the bus terminal. They buy tickets for Wilmington separately so as not to be recognized as a group of four. Dicey sleeps on the bus, and when she wakes, she feels renewed, as though she is both mentally and emotionally far from the deadening atmosphere at Eunice's. The children tease each other and laugh in the back of the bus, and at this moment, Dicey experiences the thrill of traveling, reconciling herself with the sadness and abandonment that have set them out upon this adventure.
Dicey begins to worry about money, as she wants to keep enough money for them to get back to Bridgeport if necessary, she knows they cannot ride the bus much longer. In Wilmington, they find that the next bus to Crisfield does not leave until the next morning, Dicey, who is afraid Eunice will be looking for them, impulsively buys tickets to Annapolis, on the opposite side of the Chesapeake Bay. In Annapolis, the children wander around the sunny, relaxed city, enjoying being once again so close to the water. When James finds they have traveled to the wrong side of the bay, he questions Dicey, who admits that she had not planned for them to travel together even though traveling together was the right thing to do. The younger children suspect Dicey, too, might have abandoned them, but she asserts that this is not true. The children find an abandoned house and sleep on the porch, as they had on their first night traveling. They sing quietly and happily into the night.
Dicey, no longer certain how much money she has left, pulls another twenty dollars out of her reserve and uses it to buy camping supplies at an Army Navy store. The children, uncertain of their plan, wander down to the boatyard, where they find two teenaged boys, Tom and Jerry, horsing around on a sailboat. The children talk to the two boys, who explain that they have been best friends their entire lives. Dicey senses that some of the things they tell the Tillermans are lies. The boys brag about their sailing abilities and their willingness to disobey Jerry's parents and take the boat out without permission, so James and Dicey quickly fabricate a story about their having to visit a relative on the eastern shore the next day. Before long, Tom has talked a reluctant Jerry into taking the Tillermans across the bay the next morning without his parents' permission. When they leave, Dicey congratulates James for his artful manipulation of the boys, but he defers, stating the Tom had done most of the manipulating. That night, the Tillermans feast triumphantly on hamburgers, and James and Dicey consider the boys' odd behavior, wondering if friendships so often consist of dares and bravado. They ruefully realize that the Tillermans rarely have friends. James asks Dicey about their grandmother, and Dicey explains that she is probably poor, strange, and solitary. That night, Dicey counts her money. Determined to keep forty dollars for their return trip, she realizes they only have seven dollars to get them to Crisfield.
The thrill of traveling breathes life into the children and their relationships with each other once again. They talk to each other honestly, Dicey telling Maybeth that they may have to go back and admitting to the rest that she had wanted to travel alone but is glad they are together. They begin to play with and tease each other, sharing jokes and laughter, which had been extinguished and repressed at Eunice's. Most importantly, they sing together at night in Annapolis, the first time the have sung since their night in New Haven. Voigt explains that singing symbolizes one of the book's major themes, reaching out, and indeed, by the time they are singing in Annapolis, the children have refreshed and reinvigorated their connections to one another.
This renewed vigor and sense of connection crucially allows Dicey to reconcile herself with what has gone before. She understands that while Momma's abandonment of them has caused them immeasurable anxiety and physical peril, it has, at the same time, launched them on an incredible adventure in which they drift in and out of the lives of others, some who have a long-term positive impact, like Windy and Stew, and some, like Louis and Edie, who do not. Moreover, this adventure binds Dicey and her siblings together: their sheer rootlessness has forced them to put down deep roots in one another. They rely upon each other, and their being together becomes clearly and simply their lives' highest priority. Most importantly, perhaps, their itinerancy teaches Dicey an important lesson about the impermanence that characterizes all life experiences. She understands that as long as she can remain with and protect the small group of people whom she loves dearly, she can let go of anything else and face any other loss and unexpected development.
The Tillerman's overriding commitment to one another and their suspicion of all others outside of their circle also evidences itself in their perceptions of Tom and Jerry. Dicey and James watch Tom and Jerry with almost detached curiosity, puzzled by the way in which Tom pushes Jerry to take unnecessary risks when he himself has little to gain. The Tillermans are also artful manipulators: Dicey has lied to the policeman in Peewauket and to Lou and Edie, and Sammy has lied to the woman in the bakery near the Connecticut River. The Tillermans, however, manipulate others only to protect themselves or to acquire resources they desperately need, and cannot understand the teasing, daring, and cajoling that characterizes Tom and Jerry's friendship. Their family's difference and their constant traveling have prevented Dicey and her siblings from ever forming bonds with anyone other than family members. They feel they can only trust their true selves with each other, having shared the same ambiguous home experience.
The Tillermans travel bravely towards their grandmother's house, sustained by the hope that their grandmother will accept them for who they are and take them in. Similarly, as they traveled headlong towards Bridgeport, they were sustained by the fantasy that Momma would be there, waiting for them. The novel suggests, however, that their grandmother will, like Momma, not live up to their wild and unfounded expectations. Dicey knows their grandmother only as the sour-faced girl in the pictures of Cilla, the stoic wife of the cruel John Tillerman, and the old woman who lives alone on a farm and screams when people come to visit so as to drown out their words. However, Dicey applies her usual coping strategy: she concentrates on one problem at a time and trusts that she will find the inspiration to deal with the next problem when it arises.