The next day, Dicey decides that they must earn money picking tomatoes, despite the fact that she has money stored away. When the Tillermans see a sign, they walk up a long and dusty driveway to a run-down farmhouse, beside which a vicious dog is snarling and slobbering. When the owner, Rudyard, emerges, the dog cringes and cowers. The man agrees to hire the children as pickers, and asks only for their surname (Dicey gives him their father's name, Verricker). He looks at the children and his eyes linger on Maybeth. The children sense something is wrong, but set out to pick for the afternoon and earn money. Halfway through the morning, Sammy and Maybeth stop picking and go to explore, reporting back to Dicey that they can easily cross the nearby river by swimming it. Rudyard returns with lunch, which the children are too anxious to eat. Although Dicey informs him that they cannot pick anymore, he drives off, leaving the dog chained to a tree, and does not return until nightfall.
By this time, the children are sure he means them harm, and Dicey concocts a plan. Once he fetches the dog, Dicey will set the truck running and jump out, while the children will run as quickly as they can for the river. When Rudyard arrives and Dicey sets the truck in motion, he releases the dog, which, fortunately for the children, is so hungry he ignores the children in favor of the lunch they have abandoned. The children dive into the river and begin making their way downstream in the water. They hear Rudyard shuffling around in the brush upstream, but finally he disappears, and the frightened children climb up on the opposite bank and sleep.
When they wake, the children set out for Hurlock, and Dicey finds herself suspiciously inspecting each house, wondering what threats it might hold within them. When they reach the town, they are petrified by the sight of Rudyard in his pickup truck. Panicked, they run for the circus, which has just arrived in town, reasoning that they can disappear into the crowd. However, Rudyard has anticipated them and is hot on their heels by the time they reach the tents. When Sammy trips, Dicey turns to face the approaching man. He threatens to release the dog on her, but before he can, Claire appears from the tent, cracking her whip at him angrily. Will appears beside the children as well, and Rudyard explains gruffly that the Tillermans are his foster children. When Dicey protests, Will insists on seeing papers before releasing the children. Rudyard bitterly calls Will a name, and Claire snaps her whip at him viciously until he retreats.
Will takes the children aside, and Dicey tells him that they are trying to find their grandmother in Crisfield. Will offers to let the children stay with the circus, which is traveling to Salisbury the next week, and says he will drive them down to Crisfield while in Salisbury. That night, Dicey treats her siblings to rides and the circus, finally giving up her worries about money. She determines that she must spend the money now to take care of them, and if she finds herself wanting money in Crisfield, she will earn it then. The children sleep in Claire's trailer, and when she wakes, Dicey finds herself wondering if their grandmother, like Rudyard, is a bad person, and what they will do then. Finally, Dicey relinquishes her worrying and planning, and decides that she will take things as they come.
That day, Will takes them into town to buy them clothes, and also has Dicey tell a pastor about Rudyard. The pastor asks her to talk to the police, but she declines. Later, Dicey decides that she is glad she remembers Momma and wants Sammy and Maybeth to remember her, too. That night, Dicey begins to notice that the circus acts are contrived and pre-planned, down to the smallest mishaps and clowning, and Dicey is slightly bothered by this. The days pass in a blur, and soon they are in Salisbury.
Rudyard demonstrates to the children more than any other character in the book just how vulnerable they are on their own. Rudyard has a place in which he could hold them if he wanted, he has money which tempted the children onto his land in the first place, he has an angry dog and a car to pursue them, and he has the credibility and legal power of an adult, which he tries to abuse when he tells Will and Claire that he is the Tillermans' foster father. After their encounter with the man, fears crowd Dicey's mind, as she envisions the possible evil lurking inside every house they pass. She worries that their grandmother may not be a good person either. Rudyard has broken the illusion that they are independent and self-sufficient, and now worries for their safety consume Dicey as worries about money once did.
Eunice embodies one disastrous outcome for the Tillerman children: the breaking of their spirits and the eventual breaking of the bond between the children. Rudyard embodies a far more sinister outcome. By abandoning the chance Eunice offered them, the Tillermans are taking the risk of falling under the power of an evil person like Rudyard. This risk demonstrates how dearly they hold the possibility of becoming, or retaining, their status as a family. The risk also demonstrates that they have come to rely not only on their own ingenuity, but also on luck and the kindness of the people they meet. Will and Claire save the Tillermans from Rudyard, demonstrating that the good in the world counterbalances if not outweighs the evil. Dicey is a pragmatic and unsentimental girl; she sees that chance affects her life and comes neither to self-indulgently expect good fortune at every turn, nor pessimistically expect bad fortune. Dicey learns to accept good and evil in stride, and does not let their existence color her expectations for her future.
The circus symbolizes the Tillermans: like the Tillermans, it moves around from place to place, making transient friends, and putting on a show of illusions, for the entertainment of others and for the furtherance of its own ends. During her stay at the circus, Dicey's own infatuation with transience, sparked first by their hard but successful journey from Peewauket to Bridgewater, and intensified by her brief experience sailing, grows even stronger. She often finds herself lost in dreamy contemplation of life and its vicissitudes during their days with Will and Claire. While Dicey is part of the circus, she learns a valuable lesson about letting go. She learns to let go of her worries about money and the future. She reasons that she must trust herself to provide for herself in the future, for she has a limited ability to control the future, and only wastes her own time and energy trying to prepare for whatever contingency she can imagine. Dicey's experience with Rudyard teaches her that worrying about money for tomorrow can cause problems today. When she begins to worry about her grandmother and all the possible outcomes of their meeting, she realizes she cannot even anticipate, much less plan for, every possible outcome. Thus, Dicey finds a greater peace with the indeterminacy of their journey.