Olive Kitteridge is a novel by author Elizabeth Strout. The story follows the main character, Olive Kitteridge, as she deals with the daily life of living in a small town in Crosby, Maine. As a high school math teacher, Olive Kitteridge is responsible for teach many of the children that live in the town, once they are old enough to attend high school age. This type of interaction, plus the fact that everyone knows everyone in this small town, leads Olive Kitteridge to form her own opinions and judgments on the various people that live in the town.

Olive's opinions and judgments are not just reserved for the other people that live in Crosby. Olive also has strong opinions and judgments when it comes to her pharmacist husband, Henry Kitteridge, and her only child, son Christopher Kitteridge. The author introduces a series of characters in the novel and then weaves together how these people fit into the life of Olive Kitteridge.

When Olive is younger, married to Henry, and still in the process of raining Christopher, her point of view on life seems to be set in stone. As Olive ages and Olive faces numerous adversities in her life, including Henry having a major stroke where he can't see or speak, Olive's point of view on life starts to change. By the end of the novel, when Henry is dead, Olive starts a new chapter in her life with a recently widowed man in Crosby, Jack Kennison. For the first time in her life, Olive starts looking forward to living rather than focusing on the day when she will die.