George Willard is the main character who appears in most of the stories. A thinly disguised representation of the author Sherwood Anderson, George is an earnest young man who listens to the stories other residents of the town tell him about their lives so he can think and write about them. He leaves Winesburg and his childhood behind in the final story, "Departure."
Elizabeth is described in "Mother" as "tall and gaunt," and more or less ill all the time. She is devoted to her son, George, and wants him to have a chance at life she never had. She is even prepared in her mind to murder her husband, Tom, in order to ensure George does not follow his father's advice. Her friendship with Doctor Reefy has the effect of easing her illness, but by the end of the book, Elizabeth dies in "Death," an event that adds to George's determination to leave Winesburg.
Doctor Reefy is described as "an old man with a white beard and huge nose and hands" in "Paper Pills." He is, like George Willard, able to listen to what his patients have to say. He has the habit of writing down his unsaid thoughts on small pieces of paper, and wadding them up into his pockets only "to become round hard balls."
Helen White attracts many suitors because she is the young daughter of Winesburg's wealthy banker. She is interested when a suitor tells her he wants to become a writer in "The Thinker." Although she and George are attracted to each other in "Sophistication," they make no promises to one another. Helen shows no outward sign of venturing out on her own, and seems destined to marry, and live her life, like so many others, in Winesburg.
Kate Swift is described in "The Teacher" as intelligent, well read, and well traveled. In "The Strength of God" she is seen by the Reverend Curtis Hartman as a challenge to his prayers to lead a "blameless life." George Willard is one of Kate's former students in whom she attempts to instill a depth of meaning and perception beyond that of the ordinary people who populate Winesburg.
The Reverend Curtis Hartman is described as "forty years old, and by his nature very silent and reticent." He works very hard on his sermons, despite the fact his congregation remains uninspired by them. Curtis's determination to "keep his feet in the true path" is upset when he peeps at Kate Swift through a neighboring window. In an effort to encompass the effect this has on him, Curtis concludes in "The Strength of God" he has triumphed in understanding Kate "an instrument of God, bearing the message of truth."
Tom Willard is described in "Father" as "a slender, graceful man with square shoulders, a quick military step, and a black mustache." He is very alienated from his wife. Opinionated and interested in politics, he is gregarious, and always eager to offer advice on everything. Although he looms as a threat to George's future in the early story, "Mother," Tom is barely a shadow in the final story, "Departure," as he carries his son's bag, and tells him to be careful of his money.