Richard Kirtland Woodruff was born on November 1, 1840, in Westbrook, Connecticut, to Richard Woodruff and Mariah D. Kirtland. His father was a minister. Woodruff attended Hartford High School before enrolling at Yale College in 1859. He left college in 1862 after his junior year in order to enlist in the Union army. He enlisted on August 25, 1862, and mustered in as a corporal in Company I of the 15th Connecticut Infantry on August 25. The regiment took part in the Battle of Fredericksburg in December 1862 and the Siege of Suffolk in early 1863 before being stationed in Portsmouth, Virginia. On March 23, 1864, he became a captain in the 30th Connecticut Colored Infantry, which eventually became the 31st USCT Infantry. He was placed under arrested on April 30 for an unknown offense, but he was released on June 2, 1864. He was wounded in the left arm on July 30, 1864, during the Battle of the Crater. According to one writer, the “wound disabled him from further service, but was not thought to be of a serious character, and he proceeded towards home as far as the hospital on Davids Island, N.Y.” While he was there, however, he contracted tetanus, and he died on August 11, 1864.