Winston, a farmer in Campbell County, VA in 1860 and brother of Charles J. Winston, enlisted as a private in Co. G of the 11th VA Infantry on May 26, 1861. He was wounded during the Seven Days Battles near Richmond, VA sometime between May 26, and June 1, 1862. Although the records do not indicate the exact date, which battle, or the extent of his wound, his 1926 pension application indicates he was wounded in the shoulder. He was taken prisoner of war at the battle of Gettysburg on July 3, 1863 and sent to the prison camp at Fort McHenry, MD and then on to Fort Delaware, DE on July 6, 1863. He is quoted in a family letter as having been wounded during Pickett's Charge and left for four hours on the battlefield before his capture. On October 26, 1863, he was transferred to the prison camp at Point Lookout, MD, where he remained until he was exchanged on February 13, 1865. Whether or not he rejoined his regiment is unclear, but a family letter indicates he took part in "the last battle at Petersburg," and on his 1926 pension application, he states that "after the surrender at Appomattox I made my way to Greensboro, N.C. On my arrival Gen. Johnson [Johnston] surrendered and I left the service."
After the war, he farmed in Amherst County, VA through at least 1910. By 1920, he was retired and living in Southampton County, VA. He died March 14, 1934 and is buried in Spring Hill Cemetery in Lynchburg, VA. His obituary in the Franklin, VA
Tidewater News states that he was:
Always present at the dinners given here
by Agnes Lee Chapter, United Daughters of the Confederacy, on June 3 of each
year, he never failed to proclaim himself an "Unreconstructed Rebel," and say
that he was "ready to fight again."
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