Wing Biddlebaum is a 40-year-old former schoolteacher who lives a deeply isolated life in Winesburg, Ohio. Though he is relatively young, trauma makes him appear decades older. He works as a day laborer picking strawberries, a job at which he excels due to his extraordinarily quick and expressive hands. He lives in constant fear of his own physical gestures and actively avoids the townspeople, struggling with profound loneliness.

George Willard is a thoughtful young reporter for the Winesburg Eagle and the son of the local hotel owner. He serves as a sympathetic listener to the town's various isolated residents. Possessing a natural curiosity, he observes his friend's strange fear of physical expression but respectfully refrains from pushing for an explanation, prioritizing their bond over his own inquisitiveness.

Henry Bradford is a saloon owner and the father of a former student. He embodies the aggressive, traditional masculine values of his rural community. When rumors arise regarding the local schoolteacher, he reacts with explosive physical violence, showcasing how quickly societal prejudice can manifest into direct harm.

Tom Willard is the owner of the New Willard House, the local hotel in Winesburg. His established business roots his family firmly within the fabric of the small-town community.