Elmer Cowley is the son of Ebenezer Cowley, a farmer who sold his farm a year ago and became a storekeeper. Ebenezer is not much of a merchant, as he just buys up a jumble of things that cannot really be sold. One time, Elmer threatens a merchant who tries to sell them an item they will never be able to sell again. He is bitter that his family is so odd and he thinks that everyone in the town laughs at them because of it. He takes a walk and tries to talk to a simple-minded man who remained on the Cowley farm, but he is unable to communicate his frustration. When he sees George Willard happen to look at him, Elmer flies into a rage, thinking the reporter is considering how odd the Cowleys are. Yet, when he confronts George, he cannot find words to tell him how he feels and just sputters with anger. He steals $20 from his father to take the local train to the city, where he plans to join the anonymous rush of people. He wakes up George and tells him to come down to the station, intending to tell the young man that he is not strange. Again, words fail him, and he gives George the $20 to return to his father and then beats up George before jumping on the train.
Elmer believes that “George Willard. belonged to the town, typified the town, represented in his person the spirit of the town.. Did he not represent public opinion and had not the public opinion of Winesburg condemned the Cowleys to queerness?” (195). George is again thought to represent the town because he is the reporter, collecting the stories of everyone in town. For Elmer, making himself understood to George would vindicate him in the eyes of the town. He wants to be considered normal, to blend into a crowd, which is why he is going to the big city, where he expects to disappear into anonymity. However, even in the big city, there is loneliness. Elmer is lonely in a small town because he stands out, but Enoch was lonely in a big city where he blended in.
The characters hope that moving from one place to another will give them a chance to make a meaningful connection with another person. This is why trains are so prominent in this book. Travel is a modern condition, in which people can leave small towns or cities easily. However, they cannot flee the essential human condition of loneliness, which just takes different forms in different settings.