Olive Kitteridge is structured such that only some of the chapters are focused are Olive. Those chapters not focused on Olive are basically a short story that reveals something about Olive's town, but she is merely a passing character or reference. To summarize, I will focus on the narrative arc surrounding Olive, and less upon the short stories.

Pharmacy: Henry, Olive's wife, owns a pharmacy. He hires an employee, Denise, who he begins to care for deeply, though not sexually. He helps Denise and her husband (also Henry) until Henry is killed in a gun accident. Henry K. begins to take sleeping pills from the pharmacy and Denise remarries and moves away. Years later they communicate through letters that she sends on his birthday.

Incoming Tide: A young man, Kevin, has returned to Crosby, Maine (his hometown). He is planning to commit suicide in the marina. While he sits in his car, Olive Kitteridge comes to talk to him. Before she can leave, they notice a young woman fall into the water while trying to pick flowers. Keven runs out to save her.

The Piano Player: Angela O'Meara plays piano in a local cocktail lounge, in spite of her stage fright. Olive and Henry are seen walking through the bar, but that is the extent of their involvement.

A Little Burst: Christopher, Olive's son, marries a woman named Suzanne. She is from out of town. Olive does not like Suzanne, and after the wedding, she steals some small items from Suzanne's room to try fill Suzanne with doubt, and to give Olive a small bit of pleasure

Starving: Harmon sees a young couple at the do-nut shop on his way to Daisy's house. He is married, but he sleeps her because his wife is no longer interested in a sexual relationship. Several weeks later the young woman stays at Daisy's house because she had a fight with her boyfriend. She is anorexic. Olive arrives doing charity work. The three work to help the young girl and she is committed to a hospital. She leaves the hospital and secretly starts taking laxatives. She dies from a heart attack.

A Different Road: Olive stops at a hospital to use the bathroom on the way back from dinner. She says she's fine, but the nurse asks to check her out, all the same. While being examined, two men enter the hospital and hold them up at gunpoint. The nurse, Henry, Olive, and the doctor are all kept in the bathroom by one of the assailants. Olive and Henry say things to each other that they regret, but cannot forgive. We learn that Olive writes the assailant in jail, and appears to be in love with him.

Winter Concert: Bob and Jane Houlton attend a winter concert which Olive and Henry are also attending (they are seen across the auditorium). Jane learns, through a comment of another couple, that Bob had visited a woman in Florida years ago. Jane forgives her because they are old, and have nothing but each other.

Tulips: Christopher and his wife move to California but Suzanne soon leaves him. Henry has a stroke after getting the groceries. Louise Larkin, a woman whose son stabbed a girl to death, sends a note of condolences. Surprised by the gesture, she goes to see her. The woman is mad.

Basket of Trips: Marlene Bonney's husband dies and Olive attends the funeral. At the wake afterward, Olive is comforting the widow, who asks Olive to remove a basket from the closet. It is full of brochures full of trips Marlene and her husband would look over, pretending they would go on them when he got better. Olive realizes talking about grandchildren with Henry when Christopher was so unhappy in his marriage was her basket of trips.

Ship in a Bottle: Winnie Harwood, 11, and her sister Julie live with their slightly odd mother. Julie has just been left at the alter, but with Winnie's help, she hides the fact that she escapes to Boston to live with the man who was to marry her. Olive is mentioned, in passing, as Julie's math teacher.

Security: Christopher asks Olive to come visit him in California to meet his new wife and her children. The visit starts well, but soon Christopher and Olive have a fight. He has been in therapy and tells her everything she did wrong as a mother. Olive returns to the airport, but gets stopped at security when she refuses to take off her shoes, and makes a comment about not caring if they all get blown up.

Criminal: Rebecca Brown begins stealing small things from a doctor's office. She orders a shirt from a magazine for her boyfriend, but realizes he will hate it and, so, returns it. In the end, she decides to start a fire, to get arrested.

River: Henry has died. Olive takes walks daily along the nearby river. There she meets Jack Kennison, a man from town she never liked, whose wife has just passed away. They begin a relationship in spite of their differences because they were lonely and needed someone.