The book is a collection of 13 interconnected short stories revolving around Olive Kitteridge, a retired schoolteacher living in a small town in Maine. Olive is a complex character with a prickly exterior but a deep well of emotion and empathy beneath the surface. Through her interactions and relationships with various town residents, the book explores themes of love, loss, aging, and change, painting a rich portrait of a community and its inhabitants.

The novel follows the life of George Caldwell, a high school teacher in a small town in Pennsylvania, who is struggling with feelings of disappointment and failure. He is constantly compared to his father, a mythological centaur, symbolizing the conflict between the mundane and the extraordinary. The narrative alternates between the modern world and the mythological realm, exploring themes of identity, disillusionment, and the struggle between the human and the divine.

A gifted artist, Harriet Burden, frustrated by the lack of recognition she receives due to her gender, conducts an experiment where she presents her work under the guise of three male fronts. Her plan backfires when the third front, Rune, refuses to admit that the work was not his own. After Rune's sudden death, Burden reveals her experiment, but is met with skepticism and scorn. The novel explores themes such as gender bias in the art world, identity, perception, and the nature of art itself.