Penn enlisted as a private in Co. H of the 42nd VA Infantry on May 22, 1861 and shortly after became captain. He was wounded in the left leg at Antietam, MD on September 17, 1862. Penn was taken prisoner and had his leg amputated above the knee on September 18, 1862. He was imprisoned in Baltimore's Fort McHenry on October 11, 1862 and exchanged at City Point, VA on December 4, 1862. Penn resigned due to disability on February 23, 1863. He was promoted to major on January 24, 1863, and was promoted to lieutenant colonel and colonel in April 1863, after his resignation from the army.
After the war, he was a lawyer, judge, and state senator. Penn died September 27, 1895 and is buried in City Cemetery in Roanoke, Virginia.
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