Charles Waddell Chesnutt was born in Cleveland, Ohio, on June 20, 1858. Even though he identified as Black, he could pass as white but chose not to do so. His father, Andrew Jackson Chesnutt, was the son of a white slave owner and his Black mistress.

His mother, Anne Maria Sampson, was the daughter of a free biracial couple from Fayetteville. Her parents were freed slaves who left North Carolina for Ohio to be with relatives before the Civil War and moved back to North Carolina after the Civil War and the resulting emancipation.

Chesnutt attended the Howard School. He was a teacher in Charlotte and moved back to Fayetteville to teach. Upon his return, Chesnutt became first the assistant principal and then eventually the principal of the Fayetteville State Normal School for Negroes. At the age of 20, he met and married his wife, Susan Perry, a teacher. They had four children, and one of the daughters, Helen Maria Chesnutt, became a noted classicist and published a biography of her father.

The couple was increasingly concerned about racial prejudice, poverty and limited job opportunities in the South, so they moved to New York and later to Cleveland. While earning a law degree, Chesnutt worked as a stenographer for the Nickel Plate Railroad Company. He established a lucrative court reporting business that made him financially prosperous.

Chesnutt also began writing stories during this time. He was the first African American to have his short story, "The Goophered Grapevine," published by a national magazine, The Atlantic Monthly.

He was one of the most prominent African American novelists who produced profound works of fiction that exemplified racial prejudice in the 19th and 20th centuries. His first short story, "Uncle Peter's House," was featured in the Cleveland News and Herald in 1885. His literature told stories of the post-Civil War South. His first book, "The Conjure Woman," published in 1899, is a collection of seven short stories set in Fayetteville and examines pre and post-Civil War race relations. Between 1885 and 1905, Chesnutt published more than 50 short stories, essays, articles, books, lectures and novels. He also published a biography of the anti-slavery leader Frederick Douglass. Two of his books were adapted as silent films, and several of his works have been published posthumously.

Chesnutt worked with Booker T. Washington and W. E. B. DuBois and became one of the early 20th century's most prominent activists and commentators. He served on the General Committee of the newly founded National Association for the Advancement of Colored People (NAACP). He also toured on the national lecture circuit in the northern states.

Fayetteville State University's library, The Charles Waddell Chesnutt Library, is named in his honor. The library contains a collection of artifacts ranging from photos, legal records and valuable information. The National Association awarded Chesnutt the Spingarn Medal for the Advancement of Colored People for his literary achievements and for the most distinguished service of any Black person that year who acted to advance the cause of Blacks in America. He was awarded an honorary LL.D., a doctorate-level law degree, from Wilberforce University. In 2008, the United States Postal Service honored him with the 31st stamp in the Black Heritage Series.

Charles Chesnutt died in Cleveland, Ohio, on November 15, 1932, at 74. William L. Andrews wrote of Chesnutt, "Today Chesnutt is recognized as a major innovator in the tradition of Afro-American fiction, an important contributor to the deromanticizing trend in post-Civil War southern literature and a singular voice among turn-of-the-century realists who treated the color line in American life."