Winston, a farmer in Campbell County, VA in 1860, enlisted with his brother William Henry Harrison Winston as a private in Co. G of the 11th VA Infantry on
May 26, 1861. He was absent due to illness from October 15 to November 15, 1861. Winston was wounded at the Battle of Gettysburg on June 3, 1863 as was his brother William, but Charles was not taken prisoner. He was wounded again on April 1, 1865 at the Battle of Five Forks in Dinwiddie County, VA.
Winston returned to farming in Campbell County, VA. He died March 16, 1889 and is buried in the Winston-Clark Family Cemetery in Altavista, Campbell County, VA.
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