 Troy Middleton was the fifth of nine children and grew up at the end of the 19th century on a 400-acre plantation in southeastern Copiah County. The plantation was virtually a self-contained community, and he had a variety of chores to do depending on the season, with sausage-stuffing being one of his favorites. The local Lick Creek and Strong River had plentiful fish that he would catch, and he loved to hunt, particularly with his 12-gauge shotgun. While his family was Episcopal by heritage, they worshiped at the Bethel Baptist Church, a few miles west of Georgetown, the only church reachable on a Sunday morning. His education was conducted at the small Bethel schoolhouse, near the Bethel Church, but in the summertime he was tutored by his oldest sister Emily, who came home from Blue Mountain College to share her knowledge of different subjects with her family. Having exhausted all the educational opportunities available at home, Middleton's father asked him if he was interested in a college education. Finding this an attractive proposition, in the summer of 1904, at the age of fourteen, Middleton made the 172-mile train trip to Starkville, where he would begin his studies at Mississippi Agricultural and Mechanical College (Mississippi A & M), later to become Mississippi State University.
