The main character Janie Crawford, an African-American woman in her early forties, tells the story of her life to her best friend Pheoby Watson through an extended flashback. Readers receive the story of her life in three major periods corresponding to her marriages to three very different men.
The flashback in the book begins with Janie's sexual awakening which she compares to a pear blossom in spring. Not long after, Janie allows a local boy, Johnny Taylor, to kiss her, which Janie's grandmother, Nanny, witnesses.
Nanny is an elderly woman who, as a slave, was raped by her owner and gave birth to a mixed-race daughter Leafy. Nanny escaped from her jealous mistress and found a good home after the end of the American Civil War. Nanny tried to create a good life for her daughter, but Leafy was raped by her school teacher and became pregnant with Janie. Shortly after Janie's birth, Leafy began to drink and stay out at night. Eventually, she ran away, leaving her daughter Janie with Nanny.
Nanny, afraid Janie's life may follow Leafy's or her own, transfers all the hopes she had for Leafy to Janie and arranges for Janie to marry Logan Killicks, an older farmer looking for a wife. Although Janie is not interested in either Logan or marriage, her grandmother wants her to have the stability she never had; legal marriage to Killicks, Nanny believes, will give Janie opportunities. Nanny feels that Janie will be unable to take care of herself, so she must marry a man who will take care of her. Janie marries Logan Killicks.
Janie's image of the pear tree causes her to imagine that marriage must involve love—in Janie's pear tree scene, she sees bees pollinating a pear tree and believes that marriage is the human equivalent to this natural process. However, Killicks wants a domestic helper rather than a lover or partner; he thinks Janie does not do enough around the farm and that she is ungrateful. Janie speaks to Nanny about how she feels, but Nanny, too, accuses her of being spoiled. And so, Janie's idea of the pear tree is tarnished. Soon afterward, Nanny dies.
Unhappy, disillusioned, and lonely, Janie chooses to leave Killicks and runs off with the glib Jody (Joe) Starks, who takes her to Eatonville, Florida. Finding the small town residents unambitious, Starks arranges to buy more land, establishes a general store which he has built by local residents, and is soon elected as mayor of the town. Janie soon realises that Starks wants her as a trophy wife, to reinforce his powerful position in town. He asks her to run the store, but forbids her from participating in the substantial social life that occurs on the store's front porch. He treats her as his property, controlling what she wears and says, and criticizes her mistakes. He also begins to strike her occasionally. As time passes, he teases her in public about being old, even though she is only in her thirties.
Eventually, she cannot bear it and snaps back at Joe to look at himself. Starks hits her as hard as he can. Later, he gets sick, and refuses to let Janie see him. He does not realize that he has a failing kidney, a likely fatal illness. When Janie learns that he might die, she goes to talk to him. She tells him who she really is and says that he never knew because he would not let her be free.
After Starks dies, Janie becomes financially independent through his estate. She is beset with suitors, some of whom are men of some means or have prestigious occupations, and all of whom she turns down. She meets a young drifter and gambler named Vergible Woods who goes by the name "Tea Cake". Tea Cake plays the guitar for her and initially treats her with kindness and respect. At first Janie is doubtful of his affections, as she is older and has wealth, but eventually falls in love with him.
Deciding to run away with him, Janie has a friend look after the store, and the two head to Jacksonville to marry. They move to the Everglades region ("the muck") where they find work planting and harvesting beans. While their relationship has its ups and downs, including mutual bouts of jealousy and an episode in which Tea Cake whips Janie in order to demonstrate his possession of her, Janie realizes she now has the marriage with love that she's always wanted; her image of the pear tree blossom is revived.
However, the area is hit by the great Okeechobee hurricane, and in the chaos of surviving, Tea Cake is bitten by a rabid dog while saving Janie from drowning, and he contracts the disease. While the disease runs its course, he becomes increasingly jealous and unpredictable despite Janie's best efforts. He ultimately tries to shoot Janie with his pistol, and she is forced to shoot him first with a rifle in self-defense. She is charged with murder.
At the trial, Tea Cake's black male friends show up to oppose her, but a group of local white women arrive to support Janie. The all-white jury acquits Janie, and she gives Tea Cake a lavish funeral. Tea Cake's friends are apologetic and forgive her, wanting her to remain in the Everglades. However, she decides to return to Eatonville.
As she expected, the residents gossip about her when she arrives back in town. The story ends where it started, and Janie finishes telling her story to Pheoby.