Penn enlisted as a private in Co. H of the 42nd VA Infantry with his brother Edmund. He was wounded in the shoulder on August 9, 1862 at the Battle of Cedar
Mountain, VA and hospitalized in Charlottesville, Lynchburg, and
Danville, VA. He returned to his regiment in October, 1862. He was
wounded again at the Battle of Chancellorsville on May 3, 1863 and
hospitalized in Richmond, VA. He was promoted to lieutenant April 21,
1862 and to captain on December 11, 1863. Penn was taken prisoner at the
Battle of Fisher's Hill on September 22, 1864 and sent to the prison
camp at Fort Delaware, DE where he remained until taking the oath of
allegiance on June 17, 1865.
After the war, he returned home to Patrick County, VA where he was a merchant in 1870 and a farmer in 1880. By 1900, he had moved to Danville, VA where he was a tobacconist in 1900 and 1910, and retired in 1920. Penn died in 1927 and is buried in Danville, VA in Green Hill Cemetery.
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