Chester McMillian was born in Carroll County, Virginia, into a musical family and community. He has played traditional oldtime Round Peak style music since childhood. By the time he was eleven or twelve years old, he was living in Surry County and taking an active part in the Round Peak music community. He has played with Dix Freeman, Tommy Jarrell, Greg Hooven, and with his own group Backstep that today includes his son, Nick.
“I had music on both sides of my family,” says Chester. His father was an oldtime banjo player, and his mother’s brothers played fiddle. Chester remembers going to house dances and listening to his father and uncle play. When he was young, his father helped him make an instrument out of a cigar box. He and his brother soon acquired a mandolin and guitar, and they started playing music together.
Chester played mandolin and a little fiddle, but he eventually settled into the guitar as his main instrument. In 1962, Chester married into Dix Freeman’s family, and the two began playing a lot of music together. “Each community had their own musicians back then,” he says, adding that most musicians therefore had individual styles. Chester played guitar with finger picks on his thumb, index, and middle fingers. He worked as an auto mechanic and smashed his finger on the same day he had to play a square dance with Whit Sizemore. His middle finger hurt to up-pick, so he turned the pick around and began strumming down with his middle finger. “It’s a style that nobody else plays like,” he says.
Chester played guitar with Tommy Jarrell for fifteen years, and he developed his guitar style specifically to play with Tommy. “You just didn’t strum the guitar behind Tommy,” he explains. “I had to develop to play notes behind the fiddle and banjo.” He accompanied Tommy on numerous trips to local and national events, including trips to Washington, D.C., to perform for festivals. Chester recorded albums with Tommy, and he plays with Tommy on parts of three documentary films produced by Les Blank, Sprout Wings and Fly, Julie, and Tommy’s Fiddle.
Chester helped start the band Backstep with Greg Hooven, and Bill Mansfield. Today, he continues to perform with his son, Nick, an accomplished musician who plays numerous instruments in numerous styles. Chester has also kept busy teaching music to children in Surry County. He teaches guitar, fiddle, banjo, and mandolin beginning with the church melodies that they already know. “I teach them to play gospel,” he says, “Then they can learn what they want afterwards.” When asked what he likes, Chester says, “I enjoy all kinds of music, but I like to play the Round Peak style of oldtime music.”