Bobby is a sensitive, observant nine-year-old boy living in Cleveland, Ohio, during the late 1960s. Eager to grow up, he allows his older brother to introduce him to mature experiences, including sneaking alcohol and trying psychedelics in the nearby cemetery. He possesses a slightly humorous way of looking at the world and often struggles to interpret the complex emotions of his parents.

Carlton is a 16-year-old high school student who fully embraces the youth counterculture of the 1960s. He wears his hair in a long ponytail and sports a buckskin jacket embroidered with a blue eye. He loves rock music, dreams of the Woodstock lifestyle, and believes in taking risks. He regularly introduces his nine-year-old brother to adult substances, viewing himself as a fearless guide to the world.

Isabel is a special needs teacher who runs her household with anxious efficiency. Originally from a farm in Wisconsin, she carries the quiet grief of losing her first husband in a wartime plane crash. She struggles to manage her frustration with her family's messes. Underneath her tense exterior, she misses the simplicity of her youth and enjoys singing songs from the 1940s.

Mr. Morrow is a high school music teacher who took his job out of financial necessity rather than passion. He spends much of his time in the basement, playing the clarinet and working on a grandfather clock kit. He is a sensitive man whose face shows the wear of long-term disappointment, and he finds it difficult to bridge the generational divide with his sons.

Carlton's girlfriend is an intelligent teenager originally from New York. She brings an exotic energy to the local Cleveland counterculture and possesses a loose, graceful way of moving. Her presence introduces a new adult dynamic into Carlton's life that both fascinates and intimidates his younger brother.

Frank is one of Carlton's high school friends who embraces the hippie movement. He crashes the adults' house party alongside the other teenagers. His arrival brings rock music and an unpredictable energy to the gathering.