Gilmore studied law, but spent his career in education. He served as superintendent of schools in Athens city schools in Limestone County from 1911 to 1920, leaving to become the first principal of Hueytown High School. He also served as the school's athletic director.
Gilmore's wife, Mae taught at Hueytown. The couple had three children: Louise, Margaret and Dudley. All three went into education careers.
Gilmore is buried at Pleasant Ridge Baptist Church's cemetery. Hueytown High School's stadium was named in Gilmore's honor.