Born into a family of limited means, the ambitious Sherwood Anderson became a self-made businessman, with a fine talent for writing copy. One day in 1912, he threw away his promising career as president and lead salesman of the Anderson Manufacturing Company, makers of Anderson’s "Roof-Fix" compound. He left his wife and three children behind in Ohio and headed to Chicago, where the third book he published, a collection of short stories called Winesburg, Ohio, made him famous. His contributions to literature include his many writings, his suggestion to the young Faulkner to "go back to Mississippi and write about that little patch of earth" Faulkner knew so well, and his insistence that Ernest Hemingway try moving to Paris.

The following excerpt is from the Sherwood Anderson entry in A Journey Through Literary America:

As Anderson described it, Winesburg is a town of tree-lined streets, just like Clyde. Modern-day Clyde has “Grandmother Dunigan” to thank. She started planting maples along the old Seneca Indian trail in 1860, a trail that is now Maple Street. Her efforts were such a success that, somewhere along the line, the town fathers began offering tax rebates to those who planted trees, and the result is a green Clyde, its houses amply shaded.

Situated on the train routes and near the intersection of the old Seneca trail and Route 20, Clyde bustled. It was busy enough to become a center of commerce for the outlying areas, and solid masses of buildings, quintessential downtown blocks, grew up on both sides of Main Street just south of the railroad depot. In Winesburg, this block exists too. It houses the Willard Hotel, the offices of the Winesburg Eagle paper, doctor Reefy’s office, Hearn’s Grocery, Abner Groff ’s bakery, and Sinning’s Hardware Store. The backs of these buildings let out into alleyways that are just as interesting in their less cultivated ways as the storefronts. Anderson loved the fecund nature of the back alleys of commerce, much as he loved vacant lots gone to weed and abandoned factories.