Dicey and Gram return from their shopping trip and Mr. Lingerle, who has stayed with the younger children all day, joins them for supper. After the meal, brimming with contentment, he sits happily by the fire even after Sammy and Maybeth have gone to bed. When Gram brings up Maybeth's situation in school, Mr. Lingerle jerks up, quickly realizing that he has stayed too long and is intruding on the family's time. Gram, however, reassures him that she would have asked him to leave if she had wanted him to do so. James, after some prodding by Gram, thinks over Maybeth's problem carefully and promises to do some research on how to teach reading. Dicey feels frustrated, already anticipating that James will not follow through on his promise.
Dicey spends the next day working on her boat, and must hold in her aggravation when Sammy appears. They exchange a few words, and on his way out of the barn, Sammy bumps into Dicey, causing the scraper to gouge the wood of the boat. Dicey is ready to become angry but stops herself when she sees Sammy standing in the doorway to the barn. She finds herself remembering all the time she spent with Sammy when he was younger and realizes how unreceptive she has been toward his needs. She suggests that Sammy start sanding down the places she has already scraped free of paint, and Sammy eagerly begins working. Dicey engages Sammy in a conversation, and for the first time during the school year, truly listens to him. When he explains to her that he is consciously working to be good so as not to upset Gram, Dicey realizes that Sammy is blaming his own bad behavior in Provincetown for Momma's mental illness, and tells Sammy that Momma's illness was not his fault. She goes on to tell Sammy how much she fought when she was Sammy's age, and before long, the two siblings are teasing each other and giggling as they work.
In school, Dicey continues to rebuff Mina's friendly advances, and although Jeff manages to hold her attention long enough to sing her a song, she repels his attempts to engage her in a conversation about the song's lyrics. When she returns home after work, she finds another letter from Momma's hospital in Boston and wonders what news it contains. That afternoon, while she and Sammy work on the boat, Sammy tells her about a boy in his class who got in trouble on purpose during recess to avoid a math test. Later that night, Dicey becomes irritated when she sees James engrossed in a book, and nags at him to begin his research on reading. That night a friend invites James to spend the night the coming Friday, and Maybeth's problem, much to Dicey's dismay, recedes even further into James's consciousness.
On Thursday, Maybeth comes home from school sobbing. She had been called on to read aloud during class and made such a mess of the passage that all the children began to laugh at her. James is sobered by his sister's distress and promises her that he will teach her how to read, and Sammy agrees to take James's paper route to give him more time to teach Maybeth. On Saturday, Gram brings down sweaters and boots from the attic for the children to wear, and James looks at Dicey curiously, wondering about the contents of the attic. That night, James talks over his plan with Dicey and Gram. He wants to try teaching Maybeth to read using phonics, arguing that since Maybeth no longer has the negative emotional interference she experienced in Provincetown, she may be able to master the system this time.
In Chapter 5, by becoming involved in each other's problems, the family members start to counteract some of the outward drift that had been drawing them apart. First, Dicey and Sammy finally have a meaningful conversation about his life at school, and Dicey is able, indirectly, to tell him to be himself, assuring him that Momma's illness was not his fault and telling him that she fought with other students when she was in elementary school. Dicey has this talk with Sammy partly because of her conversation with Gram, so, in a way, Gram is present in the conversation as well. Second, James becomes engaged in helping Maybeth solve her problems in school, but only with the help of all his family members. Gram and Dicey present the situation to him as a problem he could solve, and Sammy agrees to take James's paper route to give him more time to work with his sister. Thus, each of the children seem to be making progress on their major challenges. James is making friends, Sammy is relaxing and letting go of his worry, and Maybeth is tackling her reading problem from a new and more promising angle. Their progress on these problems of the outside world serve to draw them together closer as a family.
Significantly, Dicey makes her breakthrough with Sammy when they are working together on the sailboat. First, sharing work with Sammy signifies Dicey's acceptance of Sammy on equal terms and makes it possible for her to truly listen to his words. Second, Voigt uses wood, which is both organic and strong, to symbolize holding on—a natural site for the two children to connect with each other. Dicey's work on the boat symbolizes her work with her family. First she must scrape layers of old paint off to get to the wood beneath so that she can treat the wood, much as she must scrape off layers of resistance, distraction, and selfishness to get to the wood of her family members. The wood, malleable and passive while at the same time strong and organic, gives her and Sammy the surface on which they can, once they have put aside their distractions and personal concerns, connect with each other.
Just as reminders of Momma keep surfacing in the form of letters from Boston and fleeting memories sparked by assignments and observations of her siblings, a reminder of the children's veiled past hovers above them constantly in the attic. Just as the story of Gram's children is hidden from the readers, so it is hidden quite literally from the children. The attic, James is certain, contains artifacts that would narrate the family events that led up to the birth of the Tillerman children. Gram, because she is not yet able to face these memories and their implications, guards this history from the children's eyes. Although the entirety of its contents remains hidden from the children, Gram regularly mines the attic for objects that are of use to them: shirts for Dicey, and the sweaters and boots she brings down for the other children. These mute objects tantalize the children, again giving them just a hint of the narrative they long to know. Momma and Gram have hidden the past from their children as a side effect of their own inability or reluctance to face the past, but the children long to understand what happened before them to better make sense out of themselves and their family.