As a recurring character in Sherwood Anderson's anthology of short stories Winesburg, Ohio, George Willard is a small-town boy who seeks a broader life experience than Winesburg can offer.

As "Departure" opens, the season is spring and the time is dawn: two aspects of a symbolic time-setting that implies that George's existence is undergoing rebirth. The narrator notes that, as George's father carries George's bag to the railway station, "the son had become taller than the father." This observation is meant to imply that George has outgrown his father's life in their small town and is destined for something more.

The narrator describes George as "going out of his town to meet the adventure of life," and when he looks out the window of his train car, "the town of Winesburg had disappeared and his life there had become but a background on which to paint the dreams of his manhood."

To fully understand George Willard's reasons for leaving Winesburg, another story in the collection, "Sophistication" (that precedes "Departure") observes that George "was fast growing into manhood and new thoughts had been coming into his mind." When his mother died, George had one fewer tie to his hometown. He cares for Helen White, but he wants to try to achieve success in the larger world, and he wants her to try for that, too.

Ultimately, he decides to leave Winesburg to gain experience and perspective and to try to become a writer.

Though George Willard is deeply involved in Winesburg, he decides to leave in the story "Departures"; he does so to move to the big city and get life experience so he can be a writer.

In an earlier story, the teacher talks to George. Sherwood Anderson writes:

The school teacher tried to bring home to the mind of the boy some conception of the difficulties he would have to face as a writer. "You will have to know life," she declared, and her voice trembled with earnestness. She took hold of George Willard's shoulders and turned him about so that she could look into his eyes. A passer-by might have thought them about to embrace. "If you are to become a writer you'll have to stop fooling with words," she explained

He knows that she's right. Despite his familiarity with Winesburg and the people there, he has to leave to find out about life. When he finally leaves, he doesn't have grandiose dreams of the future. Instead, he thinks about his mother and wonders what will happen in the city. He's ready to explore and see what else is out there. After his experiences as a young man, he's ready to mature into a real writer and an adult.

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.