The characters in Winesburg, Ohio are very specific to their place and time. Write a short story that brings one of these characters forward to your town. Would they be better adjusted than they are presented in the book? Would the added burden of fast-paced modern life be too much for them? Would they find help for their problems that was not available in Winesburg?

Research the Chicago renaissance of the 1910s and 1920s. Report on one of the writers that Anderson was acquainted with: Edgar Lee Masters, Harriet Monroe, Margaret Anderson, Francis Hackett, Ben Hecht, or Floyd Dell. Try to focus your biographical report on where the writer lived before coming to Chicago, and how moving to a major metropolitan area affected her or his writing.

In the twentieth century, America had gone from being a principally rural country to being overwhelmingly urban and suburban. Explore the social elements that changed society during Anderson's time, when towns like Winesburg were already becoming old fashioned.

One of the few things that is learned about George Willard's father, Tom Willard, is that he is a staunch Democrat. In "The Thinker," Tom Willard argues with a traveling salesman about the relationship between President William McKinley and Mark Hanna, the U.S. Senator from Ohio. Explore the situation that is referred to in this story and report on what it tells readers about the two men holding the argument.