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...