Olive Kitteridge
Olive is the protagonist of the book and is also the string that ties all of the stories and the characters in them together. She is already known to readers of Strout's previous book about her life and exploits, and in this series of stories she is enjoying her eighth decade. Olive was, in her younger years, a math teacher in a junior high school, and she went on to be an enthusiastic volunteer with the American Red Cross and the main museum in Portland, Maine.
Olive has recently been involved in a relationship with Jack Kennison, a widower and retired professor, but the two have split up, and prefer not to run into each other if they can possibly help it. However, Olive considers this split temporary, and actually has plans to marry Jack. She has not yet revealed these plans to her intended spouse and when she reveals them to her son Christopher, a podiatrist, they are met with ire rather than enthusiasm. Olive feels that she has failed as a mother, because she allowed Christopher to see her treat his father with anger and disdain, and realizes when she sees his wife chastising him in a similar manner that the Kitteridge apple has not fallen far from the tree.
Despite her active lifestyle, Olive has a heart attack at the age of eighty-three, and realizes that it is time to move into an assisted living facility. There, she lives in much the same way she always has done - being at the center of everything and making friends with almost every person she meets along the way. We last encounter Olive as she turns eighty-six, and is enjoying daily in-depth chinwags with her new best friend, Isabelle.
Christopher Kitteridge
Chiristopher is Olive's son, and he is a podiatrist, although surprisingly he does not convince his mother to take care of her feet until she is eighty-two years old. He is often frustrated with Olive and tends to erupt into anger, but is always berated by his wife for doing so. His relationship with his spouse mirrors the relationship between his parents that he witnessed growing up and he has repeated the patterns he saw in their marriage, which saddens Olive because she feels that she has failed him as a mother by setting him up to be henpecked.
Christopher visits more regularly as Olive gets older, and he is the one who gets her into the assisted living facility where she lives at the end of the novel.
Jack Kennison
To an extent, Jack is Olive's love interest; he is almost a decade younger than she, and the two have recently separated. Jack, a retired Harvard professor, tries to avoid Olive whenever he can, not knowing that she plans for their reconciliation. He is reaching a very nostalgic stage in his life, and for a while spends more time longing for the past than enjoying the present. Fortunately, he snaps himself out of his emotional funk long enough to realize that he still has his life in front of him and so he should be looking forwards and not backwards in the way that he does. Jack dies in his sleep next to Olive six months after returning from a cruise of Scandinavia.
Fergus and Ethel MacPherson
The MacPhersons have endured their marriage, rather than enjoyed it; giddy newlyweds at first, the joy of matrimony quickly subsided and for thirty-five of their forty-two years together they have barely communicated with each other. Fergus is passionate about re-enacting the Civil War with his historical society, and his daughter, Laurie, models her themed dominatrix work on this.
Laurie MacPherson
Laurie is the daughter of a couple who have barely spoken in decades, but she manages to thaw their relationship somewhat when she announces that she has become a domnatrix and that her performances are going to be filmed and made into a documentary.
Kayley Callaghan
Sixteen year old Kayley is taken advantage of by Mr Ringrose, the husband of the woman who hired her as a house cleaner. She is experiencing a sexual awakening which in turn leads to weekly sexual performances for Mr Ringrose, whom she finds herself becoming attached to. After he is committed to a facility for patients with dementia she finds herself walking by the building where he lives and longing for him to watch her like he used to.
Cindy Coombs
Cindy is one of Olive's former students and the two begin a friendship when they run into each other in the grocery store. Cindy is very sick and starting to untangle her feelings about her own mortality. Olive finds it easy to talk to Cindy and confides in her a great deal about the way in which she treated her husband, which is starting to make her feel retrospectively guilty even though the did not feel guilty for nagging him at the time.
Denny Pelletier
Danny is a year shy of his seventieth birthday which is making him look back on his life with a wistful and critical eye wondering what he has done wrong and what is wrong with his children. A chance encounter with a dying man, and the opportunity to witness the police saving his life, reframes his feelings about both himself and his family. He realizes that he is a lucky man and that he still has a considerable chunk of life left to live in front of him.
Isabelle Daignault
Olive and Isabelle meet at the Maple Tree Apartments where they are both living. They strike up an immediate and easy friendship and quickly become close. They both talk a great deal about their lives and Isabelle in particular seems to have a lot of regret, particularly when it relates to her relationship with her daughter.
