In the mid-2000s, Barry began releasing solo material. Armed with just his guitar, Barry recorded demos in 2004 on the side, for himself and friends. He laid down the tracks with no intentions of formally releasing the material. However, one such friend was so taken by the honesty of his music that he eventually convinced Barry to release the eight songs as is under the title Laurel Street Demo 2005. They arrived via his friend's German label, spotify:search:label%3A%22Dancing+in+the+Dark%22 .
In between touring the U.S. twice over with Avail, and working odd jobs, he took off two weeks in 2006 to lay down more material for a subsequent full-length album, using various friends and family members as backing musicians. Owing much to his blue-collar roots in Richmond -- where he spent much time riding freight trains, the candid country-tinged folk of Rivanna Junction was issued in November 2006. Followed by 2008's Manchester, and in 2010, 28th & Stonewall reached number 11 on Billboard's Americana/Folk Albums chart. 40 Miler came in 2013. In 2014 both Raising Hell & Living Cheap: Live in Richmond and the studio LP Lost & Rootless. Barry's High on 95 arrived in 2017. And “The Roads to Richmond” October 2019 on Chunksaah Records.