[1] It was originally named for John Hancock, Governor of Massachusetts and famous signer of the American Declaration of Independence, with its county seat at Houston.

During the American Civil War, Winston County gained attention for its opposition to secession, a sentiment so strong that the county is sometimes referred to as the Free State of Winston.

[5] The county today plays on its reputation as the "Free State of Winston" to attract tourists.

The county's opposition to the Confederacy is briefly mentioned in the novels To Kill a Mockingbird and Addie Pray.

[6] The civil-rights judge Frank Minis Johnson of the U.S. Court of Appeals for the Eleventh Circuit was born in Delmar, in Winston County.

1WI50, Feldman's Department Store, the Houston Jail, and the Winston County Courthouse.

[8] As of the 2020 United States census, there were 23,540 people, 9,592 households, and 6,268 families residing in the county.

At the 2010 census there were 24,484 people, 10,163 households, and 7,074 families living in the county.

At the 2010 US Religion Census:[19] Unlike nearly every other county in the Deep South, and in keeping with its history during the American Civil War, Winston County has always been a bastion of support for the Republican Party, even as the Democratic Party utterly dominated Alabama state politics from the end of Reconstruction until the passage of the Civil Rights Act of 1964.

[21] The county also voted for Populist candidate James B. Weaver in 1892.

[22] Winston County did vote for George Wallace in 1968, who was the Democratic candidate in the state.

Winston was the only county in Alabama to give a majority of its votes to Republican candidate Thomas E. Dewey in 1948 over Dixiecrat Strom Thurmond.