Young George Willard is the only child of Elizabeth and Tom Willard. His father, a dull, conventional, insensitive man, owns the local hotel. His mother, who was once a popular young belle, has never loved Tom Willard; she married him in the hope that marriage would somehow change her life for the better, because it seemed to her that the young married women of the town were happy and satisfied. Soon after her marriage, however, she realized that she was now caught in the dull life of Winesburg, her dreams turned to drab realities by her life with Tom Willard.

The only person who has ever understood her is Dr. Reefy. Only in his small, untidy office does she feel free; only there does she achieve some measure of self-expression. Their relationship, doomed from the start, is nevertheless beautiful, a meeting of two lonely and sensitive people. Dr. Reefy, too, has his sorrows. Once, years ago, a young woman, pregnant and unmarried, had come to his office, and shortly afterward he married her. The following spring she died, and from that time on, Dr. Reefy has gone around making little paper pills and stuffing his pockets with them. On the pieces of paper that become the pills, he scribbles his thoughts about the beauty and strangeness of life.

Through her son George, Elizabeth Willard hopes to express herself; she sees in him the fulfillment of her own hopes and desires. More than anything, she fears that George will settle down in Winesburg. When she learns that he wants to be a writer, she is glad. Unknown to her husband, she has put away money enough to give her son a start in life, but before she can realize her ambition, she dies. Lying on her bed, she does not seem dead to either George or Dr. Reefy. To both, she is extremely beautiful. To George, she does not seem like his mother at all. To Dr. Reefy, she is the woman he has loved, now the symbol of another lost illusion.

Many people of the town seek out George Willard, who works as a reporter for the local newspaper; they tell him of their lives, their compulsions, and their failures. Old Wing Biddlebaum, the berry picker, had been a schoolteacher years before in another town. He had loved the boys who were in his charge, and he was, in fact, one of those few teachers who understand young people. One of his pupils, however, having conceived a strong affection for his teacher, had accused him of homosexuality, and Wing, although innocent, had been driven out of town. In Winesburg, he has become the best berry picker in the region, but always the same hands that earn his livelihood are a source of wonder and fear to him. When George Willard encounters him in the berry field, Wing raises his hands as if to caress the young man, but a wave of horror sweeps over him, and he hurriedly thrusts them into his pockets. To George, also, Wing’s hands seem odd, mysterious.

Kate Swift, once George’s teacher, had seen in him a future writer. She had tried to tell him what writing is, what it means. George had not understood exactly, but he had understood that Kate was speaking not as his teacher but as a woman. One night, in her house, she embraces him, for George is now a young man with whom she has fallen in love. On another night, when it seems that all of Winesburg is asleep, she goes to his room, but just as she is on the point of yielding to him, she strikes him and runs away, leaving George lonely and frustrated.

Kate lives across the street from the Presbyterian church, and the church’s pastor, the Reverend Curtis Hartman, has learned accidentally that he can see into Kate’s room from his study in the bell tower of the church. Night after night, he looks through the window at Kate in her bed. He wants at first to prove his faith, but his flesh is weak. One night, the same night Kate has fled from George Willard, the pastor sees her enter her room. He watches her as, naked, she throws herself on the bed and furiously pounds the pillows. Then she arises, kneels, and begins to pray. With a cry, he gets up from his chair, sweeps his Bible to the floor, smashes the glass in the window, and dashes out into the darkness. Running to the newspaper office, he bursts in on George. Wild-eyed, his fist dripping blood, he tells the astonished young man that God has appeared to him in the person of a naked woman, that Kate Swift is the instrument of the Almighty, and that he is saved.

In addition to Kate Swift, there are other women in George’s life. One is Helen White, the banker’s daughter. One night, George and Helen go out together. At first, they laugh and kiss, but then a strange new maturity overcomes them and keeps them apart. Louise Trunnion, a farm girl, writes to George, saying that she is his if he wants her. After dark, he goes out to the farm, and he and Louise go for a walk. There, in a berry field, George Willard enjoys the love that Helen White has refused him.

Like Louise Trunnion, Louise Bentley also wants love. Before coming to live in Winesburg, Louise had lived on a farm, forgotten and unloved by a greedy, fanatical father who had desired a son instead of a daughter. In Winesburg, she lives with the Hardy family while she goes to school. She is a good student, praised by her teachers, but she is resented by the two Hardy girls, who believe that Louise is always showing off. More than anything, she wants someone to love. One day, she sends young John Hardy a note, and a few weeks later, she gives herself to him. When it becomes clear that she is pregnant, Louise and John are married.

After their son, David, is born, John reproaches Louise for her cruelty toward the boy. She will not nurse the child, and she ignores him for long periods of time. As she has never really loved her husband, nor has he loved her, the marriage is not a happy one. At last, Louise and John separate; shortly afterward, Louise’s father, Jesse Bentley, takes young David to live with him on the farm.

Old Jesse Bentley is convinced that God has manifested himself in his grandchild, that the young David, like the biblical hero, will be a savior, the conqueror of the philistines who own the land Jesse wants for himself. One day the old man takes the boy into the fields with him. Young David has brought along a little lamb, and the grandfather prepares to offer the animal as a sacrifice to the Almighty. The youngster, terrified, strikes his grandfather and runs away, never to return to Winesburg.

The time comes when George Willard has to choose between staying in Winesburg and starting out on his career as a writer. Shortly after his mother’s death, George gets up early one morning and walks to the railroad station. There, with the postmistress’s expression of good luck in his ears, he boards the train and leaves Winesburg behind.