In Stamps, Maya and Bailey have the advantage of a close and nurturing community to help in their growing up. As Maya describes in the first chapter of the book, once the people of Stamps see that they are "harmless (and children)," they "close in" around them, "as a real mother embraces a stranger's child...warmly, but not too familiarly." Maya and Bailey's grandmother, whom they call Momma, takes very seriously her responsibility to guide the children "in the way they should go." She demands a high standard of behavior from them, and is constantly present to them to hold them to it.
In Stamps, the people all know each other, and take an active part in raising each others' children. The church is the center of social activity, and every member of the family is expected to attend, together. Uncle Willie, who lives with Momma and the children, drills the children on their lessons, and will accept nothing less than perfection from them in their ability to perform skills like their times tables with lightning speed. In Stamps, the children are dearly loved and supported, and closely watched and guided as they grow up. Although there is the constant threat of trouble from the white population, for the most part, Maya and Bailey are sheltered in the segregated town by their black neighbors, and do not have to deal with white people very much.
Life in St. Louis is quite different for Maya and Bailey. As is the case in big cities, things are much more impersonal, and the children are left on their own a lot more. Maya and Bailey are exposed to vices rarely encountered in the small town of Stamps, the offshoots of "prohibition, gambling and their related vocations" which are practiced in plain sight. The children's mother, as an entertainer, is sometimes involved with the more unsavory elements in the city, and is away a lot, leaving the children to fend for themselves. Unbeknownst to Mother, Mr. Freeman, her live-in boyfriend, molests young Maya while she is away.
Maya finds that things are very different in the St. Louis school she attends as well. The teachers are ruder, and the students are "shockingly backward," not having had the strong familial support that Maya and Bailey were given back in Stamps. The two children are adept in their math skills because of having worked in their grandmother's store in Stamps, and are well read because in Stamps, that had been their main source of entertainment. Both Maya and Bailey are moved up a grade upon entering school in St. Louis.