George Willard avoids the festivities of the Winesburg County Fair, hiding in a stairway away from the crowds of townspeople. George is on the cusp of adulthood and is planning to leave Winesburg and work on a city newspaper. He feels lonely, old, and tired, and wishes that someone else could understand the confusion he has experienced in the aftermath of his mother Elizabeth’s death. George is lost in introspective thought and feels himself crossing “the line into manhood,” recalling childhood memories and dwelling on the self-doubt and uncertainty that he feels toward his future. He becomes aware of his own mortality and wishes for human connection and understanding.
The death of his mother has resulted in an existential crisis for George in which he questions his past, present, and future. Although he is a young man full of potential, Elizabeth’s death has forced him to mature quickly and has made him acutely aware of his own mortality. As a result, George feels alienated from the community, as he is convinced that no one could relate to his inner turmoil. Above all, George longs for companionship and understanding as he makes the transition from boy to man.
Feeling a distinct shift toward manhood in himself, George longs to see Helen White, who has come from college in Cleveland to spend the day at the fair. Although Helen is with another young man (one of the instructors from the college), she is thinking of George and remembering the time they spent together throughout their adolescence. Going to college and living in the city has given Helen new experiences and perspectives on life. George and Helen simultaneously yearn for each other to understand their newfound maturation and wisdom.
Like George, Helen White is experiencing a parallel coming-of-age in which she feels a disconnect between her imminent adulthood and the childhood experiences that are tied to her hometown. Having grown up together, Helen and George believe that they will feel completed and understood by each other’s company as they both try to navigate their newfound maturity.
On the night of the county fair, Helen and George both remember a summer evening when they had walked together through the countryside and discussed their futures. George had encouraged Helen to be beautiful and “different from other women.” Struggling to express his feelings for her, George commented that he used to think she would marry Seth Richmond but now knew that she would not. Amidst the loud spectacle of the fair, George feels dejected and tries to convince himself that he does not care that Helen is with another man. He eventually decides that he will go to Helen’s house to speak with her.
George’s conflicting feelings for Helen reflect his deep desire to understand how they will now relate to one another as adults. George has had several confusing, chaotic romantic relationships throughout his adolescence. His encouragement of Helen to be different from other women suggests that he believes her to be special, and that his own experiences have led him to hold particular beliefs about the nature of women.
At Helen’s house, her date is trying to impress her parents but comes off as rude and arrogant when he belittles Winesburg. Helen’s mother agrees with him, commenting that no one in their hometown is “fit to associate with a girl of Helen’s breeding.” Frustrated, Helen runs out into the street and calls out to George, who has coincidentally arrived at her house. Unsure of what to do or say, George takes her hand and the pair walk off into the night.
While Helen is put off by her date’s attitude, her mother’s approval reflects the sharp class divide that exists in Winesburg. Whereas most of the community is working class or impoverished, the Whites are a wealthy family that stands out from the rest of the town. Despite this, Helen still holds an allegiance toward Winesburg that leaves her feeling frustrated and disconnected from her mother and her date.
George and Helen climb up a hill to reach the Winesburg Fair Ground. George feels that his emotions are reflected in Helen and that his isolation is both “broken and intensified” by her presence. Now that the fair is over, Helen and George look over the vacant town and the narrator comments on the conflicting fondness and meaninglessness that the sight inspires. George, feeling refreshed and completed by Helen’s feminine presence, wants to love and be loved by her. He marvels with reverence at the townspeople he has grown up with and has the sense that he is insignificant in the grand scheme of life.
George feels both comforted and alienated by Helen’s presence. He realizes that men and women have complementary societal and interpersonal roles, leading to an epiphany where he feels completed by Helen’s femininity. This moment is the climax of the novel, as George’s ongoing desire to feel incorporated into the natural order of the world is realized.
George and Helen both experience a profound sense of mutual understanding and share a brief kiss. Walking back into town, the pair kiss again and feel a great respect for each other. They play and roll in the grass like children as they go down the hill. Afterward, they walk in “dignified silence” and feel that their evening together has given them something that they both needed.
Although George and Helen kiss, the time they share together is significant because it allows them to appreciate each other as more than just sexual counterparts. They are both overcome with a sense of understanding and completeness, and the night serves as a rite of passage into their adult lives.