Bolding played college baseball under Sam Holt and Bobby Wilson at Carson–Newman College in Tennessee. After serving in the United States Army, he played briefly in the minor leagues for the Elizabethton Twins. After returning from duty in Vietnam, he ran track & field at Milligan College for renowned coach Duard B. Walker. Milligan College inducted Bolding into its Athletics Hall of Fame for his multi-event Track and Field exploits while a Buffalo, where he set school records in the 440, pole vault, discus, and javelin. His 1972 47.6 second 440 time at the Davidson Relays still stands.
Bolding was the head coach of Longwood from 1978 until his retirement in 2013. During his tenure, the team moved from Division III to Division II (in 1981) and again to Division I in 2005. Bolding published his memoir "Top Half, get on base dammit!" in 2014. The 630 page book is a colorful and intensely personal narrative of his formative years, personal life, his Vietnam War service, and his subsequent highly successful 40 year coaching career. A critical review labeled this book of the legendary coach a poignant and "hard-hitting" American success story.
Longwood had winning records in 31 of Bolding's 35 seasons. His career coaching record is 953–544–4.
Longwood appeared six times in the NCAA Division II Tournament and made two trips to the Division II College World Series under Bolding. In 1982, Longwood reached the national championship with a 31–10–1 overall record. In 1991, the team won a program-record 41 games and advanced to the Division II College World Series. In Division I play in 2007, 2009, 2010, 2011, and 2012, the team finished with an above-.500 record, with records of 34–19, 26–22, 28–20, 28–18, and 27–21, respectively. His final Longwood team finished in the final four of the 2013 Big South Conference tournament.
In 2009, the Longwood Board of Visitors renamed the university's baseball complex in honor of Bolding, and established the Charles B. and Andrea G. Bolding scholarship in his and his wife's name.
Prior to the start of the 2013 season, Longwood announced that Bolding would retire following the season.
Bolding graduated from Staunton River High School in Moneta, Virginia, where he played football and baseball, and also excelled in track & field. In 1965, he was named Bedford County's Athlete of the Year. Bolding later coached his high school's varsity teams to championships in cross country and baseball before moving to the college coaching ranks.