George is a young journalist working for the Winesburg Eagle. He dreams of moving to a large city to become a writer. His youth makes him eager to interact with the townspeople, though his naivete prevents him from fully understanding their internal lives and struggles. He frequently walks around town seeking out stories and experiences, serving as the central link connecting the various residents of Winesburg.

George's mother operates the failing New Willard House hotel. An obscure illness keeps her lethargic, but she holds onto the memories of her adventurous youth and the traveling performers who once visited her father's inn. She hopes George will preserve the creative spirit she feels she lost to a life of disappointment.

The daughter of a Winesburg banker who attends college in Cleveland. She comes from a wealthy household but longs for a life beyond the rigid social expectations placed upon her by her family. She attracts the romantic attention of several young men in town and enjoys moments of youthful rebellion against her strict upbringing.

A local schoolteacher known for her strict and sometimes cold demeanor in the classroom. Beneath her stern exterior, she harbors a passionate soul and a deep appreciation for the richness of life. She reads in bed while smoking, keeping her intense emotions hidden from the community that views her as a typical old maid.

A fiercely ambitious farmer who modernizes his land with new technologies during the dawn of the Industrial Revolution. He views his life through a strict Biblical framework, frequently demanding signs of approval from God. He treats his family with ruthless authority in his pursuit of material and spiritual greatness.

Elizabeth's husband and George's father. He resents his failing marriage and the hotel's poor business. He holds political ambitions to become a Democrat governor in a Republican state and pushes his son to pursue conventional financial success.

An aging physician who spends his days isolated in his medical office. He possesses a habit of writing his overwhelming thoughts on scraps of paper, crumpling them into hard balls, and stuffing them into his pockets. He is a widower who previously married a wealthy young woman under unusual circumstances.

A reclusive man who has lived on the edge of Winesburg for twenty years. He feels highly anxious about his unusually expressive and dexterous hands, a physical trait that distinguishes him from others and caused him immense trouble in his past. He rarely leaves his property without encouragement.

Jesse's daughter, who grows up feeling excluded and rejected by her father. Her unmet desire for familial affection hardens into a volatile, antagonistic temper. She seeks connection with others but struggles to communicate her emotional needs.

The grandson of Jesse Bentley and the son of Louise Bentley. He fears his mother's sudden shifts in mood and goes to live on his grandfather's farm in search of stability and tenderness. He enjoys the outdoors and hunts with a homemade slingshot.

A quiet, reflective young man who lives with his widowed mother. He feels out of place in Winesburg and contemplates moving to the city to find work. He views himself as fundamentally different from his peers and struggles to establish genuine romantic or social connections.

A dry goods store clerk who enters a serious relationship in her youth. She spends her early twenties waiting for her former lover to return from the city, slowly confronting the reality of her fading youth and isolation. She works quietly in town while harboring intense loneliness.

An excitable oil salesman who organizes a local baseball club. He talks constantly about his unique ideas regarding the world, overwhelming those around him. He eventually uses his rhetoric to charm the people in town.

The village telegraph operator, noted for his unkempt appearance and intense hatred of women. He isolates himself from the men of the town but works with exceptional skill in his profession. He harbors a bitter history regarding his former marriage.

The pastor of the local Presbyterian church. He privately doubts his ability to inspire his congregation and struggles with intense carnal temptations that threaten his religious calling. He views his internal struggles as direct tests from God.

An artist who leaves Winesburg for New York City. He struggles to express himself clearly to others and prefers isolating himself in his room with imaginary companions. He finds the presence of real people overwhelming and threatening to his inner world.

The daughter of a bookkeeper who develops a combative personality to counter her father's mistreatment. She spends time with George Willard but harbors deep romantic feelings for a local bartender, using George to satisfy her need for attention.

A saloon bartender who previously squandered an inherited fortune. He wishes to marry Belle Carpenter and views her other suitors with open hostility, relying on intimidation to maintain his claim on her.

A young storeowner who works at Cowley & Son's dry goods store. He deeply resents his family's reputation for being strange and becomes obsessed with how others perceive him, projecting his insecurities onto the town reporter.

An ambitious young journalist who leaves Winesburg to seek employment at a city newspaper. He leaves behind promises to his girlfriend, choosing to focus on his career and new social life in Chicago.

A doctor who possesses enough wealth to get by without seeing many patients. He claims to have once been a reporter and frequently visits the newspaper office to share elusive, philosophical stories about his past with George.