Holling Hoodhood is a junior high schooler in the 1960s. Like many schools, Holling's high school has segregated itself into communities, this time Catholic and Jewish communities. Each group goes to their respective church/temple once a week for religious instruction, but since Holling is a Presbyterian, he doesn't attend either midweek class.
Holling ends up with Mrs. Baker during those weekly sessions, and he wonders if she hates him for taking some of her free time. He especially dislikes that she makes him study during this time, but eventually, they strike up a friendship. Mrs. Baker tells him about her husband fighting in Vietnam, and Holling discovers that unbeknownst to him, he has an affinity to Shakespearean plays.
Holling's home life is troubled but in different ways. Instead of having a father who won't take care of the family, Holling has a father who is domineering, both in business and in private life, and Holling feels serious pressure from his father to become just like him. Holling begins dating Meryl Lee whose father is a competitor of Holling's father. To underscore the troubles at home, we learn that Heather (Holling's older sister) has run away to California.
Holling struggles in school, but through his friendship with his teacher, and by using his newfound knowledge from Shakespeare, Holling begins navigating his social dilemma more successfully, although the final confrontation where Holling will navigate his relationship with his father is not included in the book. Instead, the book ends without a clear finale, implying that Holling will keep practicing the skills of his independence.
