Cowles was the older brother of R-MC alumni Henry Brown Cowles, Jr., and James R. Cowles and son to Rev. Henry Brown Cowles, an influential Methodist minister and agent for Randolph-Macon College. In 1860, he was living with his parents and siblings in Petersburg, VA, with no occupation listed and an indication he was attending school. He enlisted in the 21st Texas Cavalry as a private but was shortly made 1st lieutenant and assistant adjutant. A diary by his wife indicates his rank at the end of the war as captain.
Cowles was married in New Orleans in May 1866 and returned to Virginia. In 1870, he was living in Prince George County, VA, with his parents, wife and children and is listed as a farmer. He moved to Texas in the 1870s (probably after his father's death in 1874) where he was a professor and principal of the Methodist Female Academy and professor and president of North Texas Female College, both in Sherman, TX, in the late 1870s. In the 1880 census, he is listed as a teacher in Terrell, TX. Later in the 1880s, he was a school teacher and school superintendant in Van Zandt County, TX. He was still teaching school in 1900. Cowles died December 21, 1904.
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