Why this Alabama county earned the nickname the Free State of Winston

Countries & Cities · Published 15 October 2026 Swipe more like this →

In short: During the American Civil War, Winston County became famous for its fierce opposition to secession. With few enslaved people in the region, residents saw little reason to join the Confederacy. Today, the county embraces this independent reputation as a tourist draw, marking a unique chapter in Southern history.

Established in 1850 as Hancock County, the region was renamed in 1858 to honor Alabama Governor John A. Winston. Its reputation as the Free State of Winston emerged from its distinct political stance during the American Civil War. Because the area had a very small enslaved population, local sentiment remained largely opposed to the Confederate cause, setting it apart from much of the surrounding state.

This spirit of political independence persisted long after the war. While the Democratic Party dominated Alabama politics for decades following the Reconstruction era, Winston County remained a consistent bastion of Republican loyalty. In 1912, it was one of only four Alabama counties to support Theodore Roosevelt’s Bull Moose Party. By the mid-20th century, its contrarian streak was even more pronounced; in four consecutive presidential elections between 1936 and 1948, it was the only county in Alabama to vote for the Republican ticket.

The county's political identity remains strong today. In 2024, Republican candidate Donald Trump secured over 91.4% of the vote, marking the highest support for any candidate in the county since 1856. Beyond its political legacy, the county is home to the William B. Bankhead National Forest and features four sites on the National Register of Historic Places, including the Winston County Courthouse and the Houston Jail. The county seat, moved to Double Springs in 1883, continues to serve as the administrative center for this rural community.

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