Winesburg, Ohio

by Donald G. Evans

Though Winesburg, Ohio is not a Chicago book, Sherwood Anderson was, to a large extent, a Chicago author. Anderson first came to Chicago around 1896, after his mother’s death; he stayed with his artist brother, Karl, and worked as an advertising copywriter until he left the city around 1900. Anderson once again departed Ohio, around 1913, after a mental health crisis that has frequently been referred to as a “nervous breakdown.” He abandoned a relatively prosperous career as a paint factory manager, along with his wife and kids. Back in Chicago, Anderson initially went back to the advertising field, but he’d already resolved to dedicate himself to becoming a serious, professional author. Here, he wrote his first novel, Windy McPherson’s Son (1916), as well as Winesburg, Ohio (1919), along the way making friends with important literary figures like Carl Sandburg and Theodore Dreiser. He lived in Chicago until 1922.

The characters that populate the interconnected story collection were inspired, according to Anderson, on the people he encountered at a Near North Side boarding house—it was located near the old Poetry Magazine offices and the old Water Tower. There, Anderson engaged in conversations with poets, painters, and other creative people he referred to as “little children of the arts.” These eccentric boarding house denizens lived on the fringes of conventional life, often searching or dreaming for something beyond their grasp. This, of course, characterized life in the fictional Winesburg, Ohio, as well.

Originally published on May 8, 1919, Winesburg, Ohio is now deeply embedded in the American literature canon. It’s been used in academic settings as a successful example of the interconnected story collection, or story cycle. It’s also been examined and discussed for its emphasis on the emotional and psychological underpinnings of the characters, as compared to a focus on plot or even thematic elements. Anderson dedicated the book to his mother, “whose keen observations on the life about her first awoke in me the hunger to see beneath the surface of lives...” Indeed, Anderson, through the book’s protagonist, George Willard, and other recurring characters, plunges to the blackest depths of human fragility, vulnerability, and perverseness. Characters come of age as easily as they die in Winesburg, Ohio, and in between there is a struggle to accept or improve or reinvent personal and generational circumstance. The stories are all set at the very end of the 19^th century. It’s a cliché to say of an old book that it remains relevant or resonates with today’s readers, but here I go: Winesburg, Ohio, a patchwork of longing, regret, loneliness, ambition, and misunderstanding, speaks to contemporary life, be it urban or rural, in ways we all understand.

Upon first being introduced to the reading public, Anderson’s unique hybrid collection, in which he layered story upon story to develop character and plot, and especially to amplify the setting, more repulsed than riveted its reviewers. Some of that simply amounted to a Puritanical reaction against Anderson’s largesse in matters sexual: lust, infidelity, premarital relations, and the like abound. For some critics of the time, reading a work in such an unconventional form was an easy thumbs down.

New York Tribune literary editor Heywood Broun wrote on May 31, 1919 that Winesburg, Ohio was “monotonous.” Other critics condemned the book as immoral or perverse. Readers from Clyde, Ohio, Anderson’s hometown and the model for the title city, reacted as to an expose—betrayed by the author’s willingness to share intimate secrets, appalled at his deep invasiveness, all the more outraged because of his accuracy. The book’s subtitle, A Group of Tales of Ohio Small-Town Life, also probably hurt reception--it has the ring of nostalgia and boosterism, both false promises. These reactions bothered Anderson considerably, especially since he felt critics had misinterpreted his explorations of loneliness and repression.

But others, including a handful of the most astute and admired writers, identified the book as extraordinary.

H.L. Mencken, in a review for Chicago American on June 28, 1919, wrote that Winesburg, Ohio, was “a piece of work that stands out from the common run of fiction like the Alps from the Piedmont plain.” He goes on credit Anderson for elevating the story form to a more “spacious” form.

Hart Crane concluded his September, 1919 The Pagan review by writing, “To end with aesthetic considerations, the style is flawless. I know of no finer

selection of ‘significant material,’ combined with proper treatment and economy of detail. America should read this book on her knees. It constitutes an important chapter in the Bible of her consciousness.”

According to Kristina Smith, writing in December 2019 for Ohio Magazine, “When Winesburg, Ohio was published, some critics lauded Anderson for being the father of realism, a new genre of writing. Although the author had penned other works, this was the first to receive national attention and solidify him as a well-known writer.”

Anderson wanted to call the collection Book of the Grotesque, and though publishers persuaded him against doing so, he used that title for the introductory story, in effect defining the term and setting the stage for the 21 sketches to follow.

In that opening story, in which an old, reclusive writer interacts with an old workman, the Biblical-sounding narrator resets our understanding of conventional attitudes toward success, morality, and empathy. “…in the beginning when the world was young there were a great many thoughts but no such thing as a truth. Man made the truths himself and each truth was a composite of a great many vague thoughts. All about in the world were the truths and they were all beautiful. The old man had listed hundreds of the truths in his book. I will not try to tell you of all of them. There was the truth of virginity and the truth of passion, the truth of wealth and of poverty, of thrift and of profligacy, of carelessness and abandon. Hundreds and hundreds were the truths and they were all beautiful. And then the people came along. Each as he appeared snatched up one of the truths and some who were quite strong snatched up a dozen of them. It was the truths that made the people grotesques. The old man had quite an elaborate theory concerning the matter. It was his notion that the moment one of the people took one of the truths to himself, called it his truth, and tried to live his life by it, he became a grotesque and the truth he embraced became a falsehood.”

“Hands” follows “The Book of Grotesques,” and we start to get how these stories interact with and inform each other. “Hands” begins a pattern in which a character’s appearance is not necessarily what it seems, and his actions not necessarily what they appear. Wing Biddlebaum—“a fat little old man”—lives in almost complete isolation at the edge of town, a twenty-year resident without any meaningful relationships, save George Willard. He’s essentially a fugitive from the small Pennsylvania town in which he one day was a beloved school master and molder of young men and the next a pedophile and pariah. His nervous, fluttering hands and his touchy interactions with students were seen as warm, nurturing gestures until a mentally ill boy told as reality his dreams of inappropriate sexual contact. Condemned, beaten, and ostracized, the man fled his old life and assumed a new identity, forever avoiding human contact and hiding his hands.

George Willard is a near-constant presence throughout these stories. He is deeply ingrained in the community, and like many fellow Winesburg residents strives to escape the only place he has ever known. As the Winesburg Eagle’s reporter, George snoops and sniffs and scoops as a matter of his profession. “The paper on which George worked had one policy. It strove to mention by name in each issue, as many as possible of the inhabitants of the village. Like an excited dog, George Willard ran here and there...” George lived in his parents’ hotel, the New Willard House, which put him in close proximity to a great many conversations and people. Something in George’s nature made people confide in him, and in many of the stories he witnesses, observes, and listens, but is otherwise invisible to the reader. He befriends even the oddest Winesburg citizens, and does not seem to discriminate based on age or circumstance. In “Respectability,” for example, George becomes a confidant of telegraph operator Wash Williams, “the ugliest thing in town. His girth was immense, his neck thin, his legs feeble. He was dirty. Everything about him was unclean. Even the whites of his eyes looked soiled.”

As George transitions between boyhood and manhood, he finds himself in liaisons, or at least flirtations, with a number of young women. George also entertains grandiose notions of a future literary career, and understands at some level that his future depends on emotional intelligence. Throughout Winesburg, George is respected as much as liked. “The idea that George Willard would some day become a writer had given him a place of distinction in Winesburg…”

While the characters and stories in Winesburg, Ohio range well beyond George, it is his hustle and ambition and trustworthiness that often carries us to and from all corners of Winesburg. We stumble into or pass Wacker’s Cigar Store, Abner Groff’s bakery, Biff Carter’s lunch room, Moyer’s Livery, Ed Griffith’s saloon, Voight’s wagon shop, Ransom Surbeck’s pool room, Cal Prouse’s barber shop, Doctor Welling’s office, and Hern’s Grocery. We meet the druggist, Sylvester West; the saloon keeper’s wife, Mrs. Willy; the dry goods clerk, Alice Hindman; the half-witted farm hand, Mook; the school teacher, Kate Swift; the night watchman, Hop Higgins; the banker, White; the housekeeper, Aunt Callie. We see Waterworks Pond, Wine Creek, Trunion Bridge, The Fairgrounds, Winesburg Cemetery, Will Overton’s berry field, the Bentley farm, and Winesburg Methodist Church. As we travel back and forth along Trunion Pike, Eagle Street, Maumee Street, Main Street and Duane Street, we brush again past all these landmarks, until our familiarity with the town is as though we, too, reside there. Certain plot elements continue or repeat or conclude over the course of the 22 stories.

To know Winesburg, Ohio is to know each character’s family tree, their vocation, their best and worst deeds. Winesburg had grown from the tiniest of towns to 1,800 people. George infiltrates even the most aloof and private Winesburg people, like Doctor Percival; the migrant told braggart stories, including one that implied he might have been a murderer back in Chicago, and based an unwritten book on the singular idea that “everyone in the world is Christ and they are all crucified.” These stories put us firmly in this small-town setting, in which so much seems familiar and routine until, slowly, bit by bit, we see a population weak with pent-up desires. In “The Teacher,” we learn that “…grief, hope, and desire fought within her. Behind a cold exterior the most extraordinary events transpired in her mind.” The story “Death” reveals the protagonist “…feeling himself an outcast in his own town.” In “A Man of Ideas,” Standard Oil agent Joe Welling, a man prone to a type of seizures, feels certain he should replace George as the Winesburg Eagle reporter.

It all leads to the concluding story, “Departure,” in which the life ahead and the life behind can never be entirely separate. George leaves Winesburg for the big city—which one, it’s unclear, though a good guess is Chicago. We feel, in the moment, as George must: as much as he craved to realize his potential outside Winesburg’s tiny boundaries, he is certainly sacrificing a great deal to do so.

As time passed, a clear verdict emerged on the importance and worth of Winesburg, Ohio. In 1998, a Modern Library panel ranked it as the 24th best English-language novel of the 20^th century. The Radcliffe Publishing Course put Winesburg, Ohio 46th on their list of the century's best novels. The ambiguity of form no doubt kept the book off many other such lists, especially since nobody seems to rank story collections. But important critics, including Anderson biographer Irving Howe, steadily praised the novel over the years; American literary icons of subsequent generations, such as Ray Bradbury (The Martian Chronicles) and Alice Munro (Lives of Girls and Women), credited the book as a major influence over their own “story cycle” masterpieces. Penguin Classics, Dover Thrift Editions, Modern Library, Bantam Classics, Library of America, and Norton Critical Editions all republished the book, keeping it perpetually in print.

Mallory Smart and her Maudlin House will release the latest edition on February 11, 2026. Kevin Maloney’s introduction and Dmitry Samarov’s illustrations are what’s new and different from the original, and those additional pieces make the Maudlin House version worthwhile.

There is a generation of readers (maybe more) unfamiliar with Winesburg, Ohio and Sherwood Anderson. Maloney’s introduction does an excellent job giving context to the collection. He writes, “In 1919, Winesburg, Ohio gave writers permission to exist outside black-and-white morality, to present real people with moral complexity, dispensing entirely with the concept of good and bad. Authors could shine a light on humanity without telling us how we’re supposed to feel, freeing writers to tell stories that are complex, familiar, and true.” Maloney also builds a strong case for Anderson’s importance as an American writer. He says, “Later, I learned it wasn’t just [Henry] Miller. Hemingway, Faulkner, Steinbeck… even Bukowski all cite Sherwood Anderson as a major influence.”

Dmitry’s sketches infiltrate the reader much like Anderson’s stories. The black, white and gray illustrations broadly suggest a scene or a character or a setting whose distinction becomes more obvious as we see more and more of them. Dmitry’s style tends more toward Raymond Carver’s stark apartments than Henry James’s lush drawing rooms. His illustrations sometimes give the illusion of shadows, but draw the eye into the busy objects that constitute the frozen moment. Just as Anderson shows us depth of feeling below a seemingly unadorned surface, Dmitry’s work is far more complex than at first glance. The “Surrender” illustration at first appears as a blob--all bubbles and ill-defined scrawls--but on closer inspection we see what appears to be Louise Bentley and perhaps the Hardy sisters, Mary and Harriet, with whom she came to live. In the story, we learn that “…a wall had been built up and that she was living just on the edge of some warm inner circle of life that must be quite open and understandable to others.” Dmitry perfectly captures and complements that idea. His illustration for “The Strength of God” depicts a still, proud-looking church; the picture, in conjunction with the story, is imbued with the almost unbearable yet quiet battle Reverend Curtis Harmon wages within himself as he peeps on a bare-shouldered woman lying in bed. Like Anderson, Dmitry allows the tension to happen off-stage. Several illustrations of George Willard get inside his furious, determined personality, while other pictures, of railroad tracks and the millinery shop window and the countryside, provide a flavor for the town that seems in sync with Anderson’s own sensibility. On a more basic level, Dmitry’s excellent illustrations give the novel extra life and are enjoyable on their own.

Donald G. Evans is the author of a novel and story collection, as well as the editor of two anthologies of Chicago literature, most recently Wherever I’m At: An Anthology of Chicago Poetry. He is the Founding Executive Director of the Chicago Literary Hall of Fame.