Episode 56 The Free State of Winston

Alabama’s Free State of Winston wanted to remain neutral during the Civil War. Winston Unionists didn’t want to take up arms against the country they loved. But in the end, Winston County’s desire to remain neutral would lead to violence

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Dual Destiny Monument in front of Winston County Courthouse PHOTO: Encyclopedia of Alabama

The “Dual Destiny” monument in Double Springs, Alabama stands as a reminder of the complicated history of the Civil War. The monument features a statue of a half Union, half confederate soldier. It serves as a visual reminder of the divide that existed within Winston County head of, and during, the Civil War.

Following the presidential election of 1860, Southern states feared the newly elected Abraham Lincoln would abolish their right to own slaves. After the election, and ahead of Lincoln’s inauguration, seven states would secede from the Union, including Alabama. They joined to form the confederate states of America. The United States government deemed secession to be illegitimate and rejected the states claims of secession.

When confederates attacked Fort Sumter in Charleston harbor on April 12th, 1861, the divide was solidified. The Civil War began.

Map of Alabama. Highlighted area was Winston County in 1861 PHOTO: Wikipedia

A majority of Alabamians were in favor of secession, but there were a large number of Union Loyalists in Northwest Alabama. Many early settlers in Winston County were Unionists who had fought in the War of 1812 or were linked by family who had fought in the American Revolution.

These Unionists found the idea of severing from the Union they, and generations before them, had shed blood to establish and protect, to be painful and disloyal. An act of Treason.

They also opposed secession because of the lack of slavery in their region. Winston County is known for its rugged terrain that was not ideal for large cotton plantations in the antebellum south.

On December 24, 1860, Alabamians elected representatives to the state’s secession convention.

The Winston County candidates were Andrew Kaiser, a planter who was prepared to vote for immediate secession. Kaieser went up against Christopher Sheats, a 21-year-old teacher who opposed secession. The vote made the region’s position clear. Sheats beat Kaiser 515 to 128.

Christopher Sheats | PHOTO: Encyclopedia of Alabama

Sheats joined his fellow delegates at the secession convention in the state capital of Montgomery on January 7, 1861. By January 11th, an ordinance of secession would be passed by a vote of 61 to 39.

Sheats passionately voiced his opposition to secession during the convention.

When the ordinance passed and delegates were asked a sign an oath of loyalty to the confederacy, Sheats refused to sign it, angering his fellow delegates. He would be arrested and later released to return to Winston County.

If Alabama could secede from the United States of America, could Winston County secede from the state of Alabama?

That was the issue discussed during a meeting that took place in Bill Looney’s Tavern on July 4, 1861. Historians estimate between 2,500 and 3,000 people met at Looney’s Tavern to discuss their plan for the future. Unionists were present from north Alabama, along with unionists from surrounding states of Mississippi, Tennessee and Georgia.

By the end of the Looney’s Tavern Meeting, three resolutions were discussed and then adopted by Winston Unionists:

“First, we commend the Honorable Charles C. Sheets and the other representatives who stood with him, for their loyalty and fidelity to the people whom they represented in voting against secession first, last, and all the time.

“Second, we agree with Jackson that no state can legally get out of the Union. (Copy statement regarding Lincoln having Jackson’s papers and the Bible). But if we are mistaken in this, and a state can lawfully or legally secede or withdraw, being only a part of the Union, then a county, any county, being a part of the state, by the same process of reasoning, could cease to be a part of the State.

“Third, we think our neighbors in the South made a mistake when they bolted and nominated a ticket, which resulted in the election of a republican. They made another and a greater mistake when they attempted to withdraw from the Union and set up a new government. But we don’t want our neighbors in the South mistreated and we are not going to take up arms against them; but, on the other hand, we are not going to shoot at the Flag of our Fathers – the Flag of Washington, Jefferson, and of Jackson! Therefore, we ask the Confederacy on the one hand, and the Union on the other, to leave us alone, unmolested, that we may work out our political and financial destiny here in the hills and mountains of Northwest Alabama.”

To be clear, the second resolution passed in Looney’s Tavern, did affirm Winston County’s right to secede from the state, but there was never a declaration of secession from Alabama.

The county became became known as the free state of winston because there was a Confederate sympathizer in the tavern that day who responded to the resolutions making an off handed remark about Winston seceding and becoming the Free State of Winston.

It was a sarcastic comment, a joke that gave a serious Unionist stand a name.

Winston County declared neutrality. Political and military leaders did not accept. The state’s position was that Winston county was still under their control and the Confederacy declared Winston County’s declaration, to be treason.

Refusing to accept Winston’s neutrality, created even more passionate and determined Unionists in Winston. They responded by forming Home Guard companies to prepare to defend the county against any threat from the Confederacy.

Winston’s desire to remain neutral was at odds with Alabama’s desire to control Winston County and enforce conscription. This would lead to ongoing violence in the region until the end of the Civil War.

Natural Bridge of Alabama, where many Winston Unionists hid out from Confederate conscription agents during the Civil War | PHOTO: Shannon Ballard

Southern Unionists Strongholds

During the Civil War, several southern regions remained loyal to the Union or desired neutrality. Learn about them here

Episode Sources

Free State of Winston. Encyclopedia of Alabama. 17 November 2008.
Christopher Sheets. Encyclopedia of Alabama. 19 November 2008.
95 Things to Love About Alabama: The Free State of Winston. Roll Bama Roll. 21 May 2019.
Free State Civil War Events and the Jasper Raid. Freestateofwinston.org.
The Incident at Looney’s Tavern. Alabama Department of Archives and History. 6 February 2014.


Theme Song “Dark & Troubled” by Pantherburn. Special thanks to Phillip St Ours for permission for use.
Additional Music: “Moving On” by Wayne Jones; “Who Can Say” by 126ers; “Pink House” by Chris Haugen; “Ambient”, “Echoes of Time”, “Falling Rain”, “Virtues”, Ossuary 6” and “Heavy Heart” by Kevin McLeod.Licensed under Creative Commons

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