Stories
"Pharmacy"
The first story centers on Henry Kitteridge, the pharmacist of the town of Crosby and husband of Olive, and his relationship with an employee, Denise Thibodeau. Henry daydreams of taking care of Denise after the death of her husband, though he still loves his cantankerous wife Olive. Jerry McCarthy, the delivery boy, eventually proposes to Denise and the couple move to Texas. Denise maintains contact with Henry through a yearly birthday letter.
"Incoming Tide"
Kevin Coulson returns to Crosby where he grew up, planning to go to his childhood home and die by suicide. While sitting in his car he is approached by Olive Kitteridge, his former math teacher, who enters his car and speaks to him frankly about his mother's suicide years before and her own father's suicide. Kevin decides not to go through with his plan. Olive notices that a former classmate of Kevin's, Patty Howe, has fallen into the dock, and Kevin rescues her.
"The Piano Player"
Angie O'Meara, who plays piano at the Warehouse Bar and Grill, is an alcoholic who can only perform in front of people when she is drunk. One winter evening she sees her ex-boyfriend Simon in the audience and she calls her married lover, Malcolm, to break off their relationship. Simon later tells Angie that her mother, a prostitute, followed Simon and propositioned him. She thinks he is lying because of his dissatisfaction with his own life.
"A Little Burst"
Olive's only child, Christopher, finally marries at the age of 38. Olive finds the wedding overwhelming since she is very close to Chris. She overhears his new bride, Sue, making fun of the dress Olive is wearing, and implying that Olive is difficult. Infuriated, Olive steals and damages some of Sue's clothes, giving her a little burst of happiness of the kind Olive depends on to make her life worth living.
"Starving"
Harmon, who runs the local hardware store, begins an affair with the widow Daisy Foster after his wife, Bonnie, informs him she is no longer interested in sex. Harmon observes Tim Burnham and his girlfriend Nina and is intrigued by their loose attitudes towards drugs and sex. When Tim leaves Nina, she goes to Daisy for help and reveals she suffers from anorexia. Olive Kitteridge, Harmon and Daisy all try to help Nina, but she eventually suffers a relapse and dies. These events cause Harmon to realize he is in love with Daisy and he rents Tim and Nina's former home, in preparation for leaving Bonnie.
"A Different Road"
Olive reflects on an occasion when she stopped at a small hospital emergency room to use their bathroom. Despite not feeling ill, she was persuaded to have an examination. The delay meant that Olive and Henry were there when two young men invaded the hospital looking for drugs. Held hostage alongside the nurse and the doctor, Henry and Olive began quarreling, with Olive disparaging Henry's mother and Henry taking the nurse's side when Olive rebuked her for praying. After their rescue, tensions remain between the couple and Olive reflects how their relationship has been affected by their experiences at the hospital.
"Winter Concert"
Jane and Bob Houlton, a retired couple, meet the parents of their daughter's friends at a concert. Jane knows that one of their daughters has had an abortion. In conversation, the couple mention seeing Bob at an airport in Miami. At home, Jane confronts Bob, who admits that, four years earlier, his former mistress had contacted him because she had breast cancer. Jane is upset by his betrayal.
"Tulips"
Olive's son Chris and his new wife have moved to California. After a year, Chris announces that they are divorcing but he will be staying in California. Olive and Henry try to adjust to retired life, but Henry suffers a stroke which leaves him unresponsive, forcing him to move to a care home. Olive finds herself contemplating suicide now that she lives alone. After receiving a condolence note, Olive goes to visit Louise Larkin. Louise and her husband have become shut-ins after their son Doyle committed murder. Louise talks about suicide with Olive and mocks her for lying to make her life appear better than it is. Shortly after visiting Henry, Olive gives him "permission" to die but he continues to live.
"Basket of Trips"
Olive helps set up the wake of Ed Bonney, something Henry would have done were he well. During the wake, Kerry Monroe, the cousin of Ed's widow Marlene, becomes intoxicated and makes a scene. Olive later finds Marlene with Kerry, who has passed out. Marlene confesses to Olive that, since Ed died, Kerry has confessed to having previously had an affair with him. She asks Olive to dispose of a basket filled with pamphlets for vacation packages which Marlene now feels unable to look at.
"Ship in a Bottle"
Winnie's sister Julie is left at the altar by her fiancé Bruce, who tells her he wants to continue dating, but does not want to get married. Julie's mother Anita threatens to kill Bruce and disown Julie if she continues her relationship with him after he left her at the altar. Nevertheless, Julie leaves on a bus to go to Bruce in Boston. Anita finds a note Julie wrote to Winnie asking her to stop her parents finding out and Winnie realizes that something between her and her mother is now broken.
"Security"
Chris has married a second time and is now living in New York City. He asks Olive to visit and she goes, realizing that Chris's invitation is only a way to get her to help out with his two young stepchildren. Olive dislikes Chris's new wife Ann, who smokes and drinks while pregnant, but does her best to help out. After an incident during a trip to get ice cream, Olive tells Chris she wants to leave and they quarrel. Olive leaves New York City and goes home early with neither her son nor daughter-in-law taking her to the airport.
"Criminal"
The penultimate story focuses on Rebecca Brown, the daughter of a minister, who starts to develop kleptomania after her father's death and fantasizes about burning things.
"River"
After Henry's death, Olive meets widower Jack Kennison, a retired professor, after she finds him having fainted on a walking path. Olive and Jack build up a friendship that blossoms into romance despite their different political beliefs. Olive begins a new relationship with him realizing she has found a reason to live again.
Critical reception
According to Book Marks, the book received a "rave" consensus, based on eight critic reviews: seven "rave" and one "positive". [8] The book received a 82% from The Lit Review based on eighteen critic reviews and the consensus of the reviews being, "A book of 13 short stories tied together by the strength of Olive Kitteridge. Haunted by loneliness and loss, Strout’s use of gentle humour and a sense of hope creates an unforgettable novel". [9] On July/August 2008 issue of Bookmarks, the book received a 
(4.0 out of 5) based on critic reviews with a summary saying, "While Strout deftly captures the spirit of small-town life, Olive Kitteridge—in its exploration of family dynamics, loneliness, infidelity, and grief—is a far cry from a provincial book". [10]
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