The novel's protagonist. Dicey is a tough, capable, and fiercely independent girl who is deeply loyal to and protective of her family members. Dicey, who is thirteen, resents school and the entire world of social conventions, and thus reflexively shuns friendships, choosing instead to devote her time to her job and to refurbishing an old sailboat in her grandmother's barn. Throughout the novel, Dicey struggles to come to terms with the illness and eventual death of her mother, and these events are part of Dicey's instruction in opening up to the world around her.
Dicey's grandmother. Gram is eccentric, protective of her independence, and deeply stubborn. Gram does not exactly regret her past, for she is too proud and practical to waste time on regret, but she lives her life with the realization that she has made numerous and serious mistakes as a result of her pride. While Gram does not make ostentatious displays of emotion, she does her utmost to ensure that she does reach out to her family members and express her love for them when it is important to do so. Gram's love for her grandchildren more often than not shows itself in her supportive and protective actions towards them and in her respect for their individuality.
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Dicey's ten year old brother. James is a serious and cerebral boy who has always been an outsider despite his desire to be liked. James often frustrates Dicey with his abstract and philosophical musings, and he tends to forget the needs of others or to lose sight of right and wrong in the interest of serving his own ends. At the same time, James' seriousness and intelligence help the family confront many of their problems.
Dicey's younger sister. Maybeth is still in the third grade. The pretty girl is detrimentally shy and still reads poorly and struggles to comprehend fractions. At the same time, the nine year old is a capable musician who reads music much more fluently than words. Maybeth's gentleness causes the family around her to want to protect her from the outside world.
Dicey's youngest brother. Seven-year-old Sammy is a rambunctious, stubborn, and good-natured. As the youngest, Sammy has the strongest and most emotional connection to Momma and in struggles more than the others to understand why she became ill and left them. Sammy works hard for causes in which he believes, but cannot be persuaded to do anything he does not want to do.
Dicey's schoolmate. Mina is a pretty, well-liked, and intelligent girl. Mina takes an interest in Dicey because she is so different from the other students. She persists good-naturedly in her attempts to befriend Dicey despite the other girl's coolness.
A tenth grader in Dicey's school. Jeff is the guitar player who sits by the bike racks outside of school and takes an interest in Dicey. He is a quiet and, a popular but private individual whose singing endears him to Dicey and finally gains him entrance into her home one afternoon after Thanksgiving.
Maybeth's music teacher. Mr. Lingerle is extremely obese and therefore, like the Tillermans, a little bit on the outside of the conventional world. Mr. Lingerle responds warmly to Gram's hospitality, and his support and generosity are a boon to the Tillermans throughout the novel.
The Tillerman children's mentally ill mother. Momma remains, for the duration of the book, in a mental hospital in Boston. The children remember her as hardworking and loving, and each child questions his or her role in the decline of Momma's health. Gram disowned Momma because Momma, having seen the sad example of marriage presented by her own parents, refused to marry her children's father.
The butcher and owner of Crisfield's market. Millie is also one of Gram's oldest acquaintances. Millie is slow with words and numbers, but Dicey grows to respect the older woman for her steadiness and constancy of heart.
Dicey's English teacher. Mr. Chappelle is dull and unwilling to question conventions. He accepts the unexceptional answers and ideas of his students, but reacts only with suspicion when Dicey turns in superior work.
Dicey's home economics teacher, Miss Eversleigh struggles diligently to convince Dicey of the importance of domestic skills. She does not, however, make a strong effort to understand Dicey and her point of view.
The owner of the wood shop in which Dicey buys several presents and finds the box for Momma's ashes. The woodworker is slow to speak, but thoughtful, caring, and skilled. He speaks respectfully, intelligently, and compassionately to Dicey as she is struggling to face her mother's death.
Momma's doctor in the mental hospital. Dr. Epstein is harried and a bit self-important. Used to being surrounded by loss and despair, he seems most concerned with exculpating himself from Momma's death, insisting to Dicey that Momma never tried to get better.
The nurse at the mental hospital. Preston is strong, warm, and compassionate. She speaks gently to Dicey and Gram and suggests they cremate Momma to bring her home with them more easily.