Jennings Chestnut evolved into a master builder of mandolins, banjos, violins, and guitars. Born in 1942, Chestnut had been a fan of bluegrass music since he was six years old. During the 1950s, Chestnut played and sang country and bluegrass with several bands. In the next decade, he traveled with his family to bluegrass festivals all over the country. In 1971, he built his first mandolin and in 1985 he and his wife, Willie opened Chestnut Mandolins, a full-service music store in downtown Conway.
Over the years, the Chestnuts continued to attend family-centered bluegrass festivals. Jennings was considered an expert in string instrument repair and was known to spend considerable time with musicians, adjusting their instruments. Although each of his mandolins required over two hundred hours of labor to construct, Chestnut donated instruments for a number of festivals to show his support for the presenters.
In 1996, Chestnut organized the 1st annual “Bluegrass on the Waccamaw” festival. Held under the bridge in downtown Conway, professional and local bands continued to perform at this free festival until Chestnut's death in 2010. Truly serving the community, Chestnut secured volunteer help from local residents and the Chestnut family cooked the meals for the performers. Chestnut strove to inspire other music advocates through his presentation of an annual “Lifetime Commitment Award” for the promotion of bluegrass music. Chestnut passed away in 2010.
In 2005, Chestnut was inducted into the Conway High School Hall of Fame and in 2006 he was awarded The Laverne H. Creel Lifetime Achievement Award from the Conway Area Chamber of Commerce. Chestnut received the Jean Laney Harris Folk Heritage Award in 2002.