Why did George Willard leave?
George Willard is essentially the main character of Sherwood Anderson's Winesburg, Ohio, as he is present in the majority of the stories in the book. On the surface level, George leaves in the last story to seek a career as a writer in the big city. However, upon further consideration, it becomes clear that George leaves Winesburg to escape the stagnation that has trapped many of the small town's inhabitants.
Anderson's collection is interesting in that it subverts the conception of small-town America as a bucolic and innocent paradise. Indeed, most of the inhabitants of Winesburg are "grotesque" in one fashion or another; plagued by fears, psychoses, anxieties, and general stir-craziness, the citizens of Winesburg seem more like isolated prisoners than happy and prosperous citizens. Within this context, George's decision to leave is an attempt to escape the stagnation crippling his neighbors. It is also a rejection of classical American values, as George leaves the traditionally idealized small town for the modern big city.