After a brief stay in New York he resigned and went to Cleveland, Ohio, where he became a stenographer in the accounting department of the New York, Chicago & St. Louis Railroad Co. A year and a half later he transferred to the legal department, where he stayed two years, during which time he studied law and was admitted to the Ohio bar in 1887. He has never practiced his profession of the law very actively, his principal occupation having been that of a court and convention shorthand reporter, for which business he has for many years conducted an office with a staff of assistants.

Mr. Chestnutt's first story was written at fourteen and was published in a North Carolina newspaper. It was intended to show the evil effects on the youthful mind of reading dime novels. Beginning in 1884 he added many stories and articles to the periodical press. His best short story, "The Wife of His Youth," appeared in the Atlantic Monthly, in 1898, since which he has published "The Conjure Woman," (1899), a volume of dialect stories of plantation life in North Carolina, most of which had shown in the Atlantic; "The Wife of His Youth" and "Other Stories of the Color Line" (1899); "The House Behind the Cedars" (1900); "The Marrow of Tradition" (1901); and "The Colonel's Dream" (1905). All of these books deal with race problem motives. Mr. Chestnutt is also the author of "The Life of Frederick Douglass," which forms one of the volumes of the Beacon Series of Biographies of Eminent Americans.

He was married at Fayetteville, North Carolina, in 1897, to Susan, daughter of Edwin and Catherine Perry, who has borne him four children. Two of his daughters are graduates of Smith College, another of the College for Women of Western Reserve University.

His only son is a graduate of Harvard University, studied dentistry in Northwestern University, Chicago and is practicing his profession in Chicago. One of his daughters, Mrs. Ethel C. Williams, is the wife of Professor Edward C. Williams, of Howard University; another, Miss Helen Chestnutt is a teacher in Central High School, Cleveland, and the third, Miss Dorothy Chestnutt, is a teacher in the Cleveland Public schools. Mr. Chestnutt is a member of the Rowfant Club, The Chamber of Commerce, The City Club, The Western Reserve Club, The Cleveland Bar Association, The Church Club, and the Council of Sociology, of which latter body he served one year as President. He and his family are connected with Emanuel Episcopal Church, on Euclid Avenue.

Mr. Chestnutt has appeared upon the platform as a reader of his own writings and has charmed large audiences with the rare skill with which he handles the dialect of the North Carolina Negro.

The Washington Times says: "There was not a dull moment in the two hours spent with Mr. Chestnutt last evening, and at the conclusion of the program he received the hearty applause and individual congratulations of his auditors."

From The Augusta Ga. Chronicle: "There have arisen many interpreters of the Negro character, but none have made him more humorous than Charles W. Chestnutt in the various stories brought together in 'The Conjure Woman.' The 'Uncle Julius' who relates these stories of Negro superstition bids fair to become as popular as 'Uncle Remus' because of his rich, lazy dialect, his characteristic dark garrulousness, and his cunning consciousness of effect his yarns have upon his hearers."

The Christian Register, Boston, says: "They are like none of the other Negro stories with which we are familiar, and take an exceptionally high place both as a study of race characteristics and for genuine dramatic interest.

In 1928, he was awarded the Spingarn Medal for "pioneer work as a literary artist depicting the life and struggles of Americans of Negro descent, and for his long and useful career as scholar, worker, and freeman." The Fayetteville State University Library is named for Chestnutt; a State Highway Historical Marker marks where he taught in Fayetteville, North Carolina; and in Cleveland, Ohio, a street and a school are named for him.