The members met in 1996 when lead singer/songwriter Dave Wilson was playing for "Stillhouse". Wilson was living in the Blue House, an infamous Raleigh crash pad and romper room for the areas hottest young musicians. The other members are banjo picker Chandler Holt, upright bassist Greg Readling, and multi-instrumentalist John Teer. Wilson and Readling were playing in the Blue House as "Stillhouse" when Teer and Holt became intrigued "to hear these guys playing original country music that didn't suck" as Holt recalls. Holt and Teer befriended Wilson at the Blue House and began sitting in with the band. Wilson, over a beer one night, asked the others if they were interested in starting a bluegrass band.
Chatham County Line began as an opening act for The Carbines, Tift Merritt's band. Chris Stamey saw them open a show, offered to record them, and landed them a record deal with Yep Roc Records. The band then went on to create five albums. Chatham County Line in 2003, Route 23 in 2005, Speed of the Whippoorwill in 2006, IV in 2008, and Wildwood in 2010.
The IV album includes a track, Birmingham Jail, that tells the story of Addie Mae Collins, Denise McNair, Carole Robertson, and Cynthia Wesley, who were killed in the 16th Street Baptist Church Bombing. In The Washington Post, Allison Stewart writes:
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