"Death," returns to Doctor Reefy and Elizabeth Willard. Elizabeth's illness is worse, and she goes to see Doctor Reefy frequently during the last year of her life. Ostensibly, she is going to see him for her health, but in fact, she visits him because she enjoys their conversations. They "renew and strengthen" her against the "dullness of her days." As she slips toward death, she thinks back on her girlhood, and on her numerous sexual liaisons, and cries bitterly over her failure to find love. She remembers her father telling her before her marriage that Tom Willard was no good, and that he would give her eight hundred dollars to take with her if she left Winesburg and started a new life. She decided to get married anyway, and her father still gave her the money, but he made her promise to hide it and never tell Tom about it. She tells Doctor Reefy this story, and that she still has the money hidden away under a floorboard, and he finds himself falling in love with her. They almost embrace, but a noise startles her, and she rushes out, suddenly embarrassed. Doctor Reefy does not see her again before her death.
When Elizabeth, his mother, finally dies, George Willard is oddly unaffected at first. He decides that now he will definitely leave Winesburg. Sitting with his mother's corpse, he begins to think of kissing Helen White. Having this thought while sitting next to his dead mother makes him feel guilty, and he begins to weep again. He leaves the room, still crying, overcome by a combination of "fright and uncertainty." The eight hundred dollars remains under the floorboard, since Elizabeth failed to tell her son about its existence before she dies.
In "Sophistication," George begins to look back on his childhood for the first time, giving him a new sense of manhood--a "moment of sophistication," as Anderson describes it. The Winesburg County Fair has set up shop in town, and as George watches the bustle of a late afternoon in autumn, his mind turns to Helen. He remembers an evening they spent together when he boasted to her foolishly about becoming a "big man," and he decides to go see her. Helen has come home for the weekend from college in Cleveland, and she, too, has begun to feel sophisticated. She has spent the day walking about with an instructor from the college, but she finds him boring and pompous, and in the evening she goes out seeking George. They encounter each other and go for a walk down to the edges of the fair ground, where they sit on a decayed grandstand as night settles in. They kiss briefly, but that impulse gives away to a sudden desire to run about in the darkness, knocking each other over like "excited little animals." Eventually, they come back into town, walking together in a very dignified fashion. "For some reason they could not have explained," Anderson writes, "they had both got from their silent evening together the thing needed."
In the final section of the book, "Departure," George Willard is leaving Winesburg. He gets up early and walks around town in the morning silence, and then makes his way to the train station. People gather to shake his hand, and he boards the train hastily, just missing Helen White, who has come to say goodbye. As the train pulls away from the station, he leans back in his seat and remembers little details of life in Winesburg. When he looks up, the town has disappeared, and has "become but a background on which to paint the dreams of his manhood."
"Death" offers, for the first time in Winesburg, Ohio, the possibility that true love will be realized, as the lives of two unhappy individuals intersect with one another. As Doctor Reefy puts it, "I had come to the time in my life when prayer became necessary and so I invented gods and prayed to them Then I found that this woman Elizabeth knew, that she worshiped also the same gods. It was an experience that cannot be explained, although I suppose it is always happening to men and women in all sorts of places." Doctor Reefy and Elizabeth share the same loneliness and desperation, and each seems to offer the other the chance to feel comfortable, finally, in life. But their courtship is doomed almost from the start, since Elizabeth Willard is both married and dying. The pragmatical impossibility of their finding happiness together exemplifies the spirit of Winesburg, Ohio, since it suggests that even when two people find one another and have a chance to escape life's powerful loneliness, fate will contrive against them. Futility, symbolized by the hidden money that Elizabeth never manages to use, is the norm in Winesburg.
"Death" also shows the maturing of George Willard, whose grief over his mother's death proves him more of an adult than at any other time. Her passing is the final moment of his childhood, and the break that enables him to make the decision to leave Winesburg and seek his fortune in the wider world. George's newly-acquired maturity is on display in "Sophistication," in which he and Helen White indulge in nostalgia for the town that both are leaving (Helen has become a college student in Cleveland). Earlier in the book, the adolescent George tries to convince Belle Carpenter of his own manhood. Now, George feels no need to prove himself, as he and Helen are secure in their budding adulthood. That they both draw back from their kiss demonstrates that their needs have changed, and that each is able to view the other not according to personal needs, but according to who the other person is. It is this security, this knowledge that they have indeed progressed in their emotional lives, that allows them to pretend to be children again. Anderson considers this ability to step away from the burdens of grown-up life critical. He writes of George and Helen that "they had for a moment taken hold of the thing that makes the mature life of men and women in the modern world possible." They have outgrown Winesburg, and one gets the sense that George, at least, may never return; he has developed beyond the constraints of small-town America, and his experience in Winesburg is no longer part of the present, but part of his past.