Dual Destiny Monument in Double Springs The Free State of Winston is a popular name given to Civil War-era Winston County, as a reflection of the county’s generally pro-Union stance and resistance to Confederate rule during the war. During the secession crisis, Unionists in Winston County declared their right to secede from Alabama; much as the state seceded from the Union. Although the county pulled back from the bold step of secession and hoped to remain neutral in the conflict, it remained under state control and was the scene of violent acts of retribution during and after the war.
Located in the rugged hill country of northwest Alabama, south of the Tennessee River, Winston County was originally formed from part of Walker County in 1850 and was named Hancock County, before it became Winston in 1858. Its rugged terrain, characterized by hills and steep-walled gorges, together with its poor soil and unpredictable climate, made subsistence farming, rather than large-scale cotton planting, the mainstay of Winston’s economy. Very few enslaved people lived in the county in 1860.
Christopher Sheats In the 1860 election, the majority of Winston County’s voters supported Southern Democrat John C. Breckinridge for president, perhaps because they saw Breckinridge as the political heir of Andrew Jackson, a hero to many of the county’s residents. From the beginning of the war, though, Winston County’s inhabitants were strongly Unionist. Christopher Sheats, a 22-year old Winston County schoolteacher and ardent Unionist, was elected by an overwhelming majority to represent the county at Alabama’s secession convention. There, he refused to sign the secession ordinance. His Unionism later led to his expulsion from the state legislature and his imprisonment for some time under charges of treason. In the first months after secession, many Winston Unionists formed home guard companies to defend themselves against Confederates. In addition, Unionists elected as officers in many of the county’s militia units refused to take the oath of office, preventing them from drilling and entering Confederate service.
Winston earned its reputation as a Unionist “free state” during a large informal gathering of Unionists from Winston and surrounding counties. One early local historian gives the date as July 4, 1861, at Looney’s Tavern, north of present-day Addison, whereas other sources suggest a later date, perhaps as late as early 1862, also at Looney’s Tavern. According to the earlier account, the Unionists passed three resolutions. The first commended Sheats for his staunch opposition to secession. The second denied Alabama’s right to secede but declared that if Alabama had that right, Winston County also had the right to secede from Alabama. The third resolution declared that those present desired to fight neither the Union nor the Confederacy and requested to be left alone by both sides to “work out our own political and financial destiny.” Although the second resolution affirmed the right of the county to secede from Alabama, it did not actually declare Winston’s secession. Nevertheless, one of those present reportedly said, “Oho! Winston secedes! The Free State of Winston!” Though the accounts may well contain some inaccuracies, a Unionist meeting did take place in the county and called for neutrality in the Civil War.
There were supporters of the Confederacy in Winston County as well, many of whom volunteered for Confederate service at the beginning of the war. The county’s Confederates held a meeting of their own on November 30, 1861. They petitioned Gov. John Gill Shorter to suppress the Unionist spirit pervading the county, to require all of the county’s residents to take the Confederate loyalty oath, and to order the county to provide 250 Confederate soldiers. Shorter responded by issuing writs of arrest for those in the county who were actively disloyal to the Confederacy and also demanding the resignations of militia commanders who would not take the oath of office.
Although Winston County’s Unionists wanted to be left alone, the governments of the Confederacy and of Alabama did not oblige. The hill-country Unionists soon faced Confederate conscription beginning in 1862 and many fled their homes, seeking refuge from conscription agents in the county’s rugged forests and canyons. The natural bridge in western Winston County was said to have been a major gathering point for Unionists avoiding the draft or who had deserted from the Confederate Army. From Winston County, many of these Unionists eventually made their way north to the Tennessee River valley and joined the Union Army, most commonly enlisting in the First Alabama Cavalry, USA. A few of the county’s residents, including Bill Looney, served the Union Army by helping Unionists escape to the safety of Union lines. In July 1862, Col. Abel D. Streight led a detachment of Union troops into the hills to gather more recruits for the Union Army. The Unionist farmers who fled into the woods and to the Union Army to avoid the Confederate draft could not work on their farms. Hence, the county’s residents had difficulty growing enough food. Confederate impressment agents worsened matters by taking food and livestock from the county to feed the Confederate army.
Natural Bridge The war produced a number of atrocities in Winston County, as both Unionists and Confederates committed acts of robbery, vandalism, and even murder against their former neighbors. One notable instance was the murder of probate judge Tom Pink Curtis by a band of Confederate horsemen who were looking for salt left in Curtis’s charge by the Alabama state government for distribution to the poor. In the later years of the war, both Union and Confederate raiders swept through the county. Confederate captain Nelson Fennel led an unsuccessful raid into Winston in June 1863 to seize deserters and draft-dodgers. Lt. Col. W. L. Maxwell led a Confederate expedition in April 1864 into the county for a similar purpose, but the rugged terrain hampered his efforts. Union colonel William J. Palmer led a raid through Winston County in December 1864 and January 1865. While in the county, his force won a skirmish with a body of Confederates and liberated a large number of Unionist conscripts. Maj. Gen. James H. Wilson led a major Union raid through the county in March and April of 1865.
After the war, considerable tensions remained between Winston County’s Unionists and Confederates, leading to occasional violence. The county’s Unionism led to Republican Party dominance of local politics. Today, a statue of a Civil War soldier, half Union and half Confederate, stands in front of the Winston County courthouse in Double Springs, commemorating the county’s divided loyalties during the war. The Incident at Looney’s Tavern, a musical drama performed many times in Winston County, tells the story of Christopher Sheats and the Unionist meeting at Looney’s Tavern. It is the official state outdoor musical drama of Alabama.
Dodd, Donald B., and Amy Bartlett-Dodd. The Free State of Winston. Charleston, S.C.: Arcadia Publishing, 2000.
Dodd, Donald B., and Wynelle S. Dodd. Winston: An Antebellum and Civil War History of a Hill County of North Alabama. Vol. 4 of Annals of Northwest Alabama, comp. Carl Elliot. Birmingham: Oxmoor Press, 1972.
Winston County Heritage Book Committee. The Heritage of Winston County, Alabama. Clanton, Ala.: Heritage Publishing Consultants, 1998.