In 2005, Giddens, who at that time was spending time competing in Scottish music competitions, attended the Black Banjo Then and Now Gathering, in Boone, North Carolina. There she met Dom Flemons and Sule Greg Wilson. The three started playing together professionally as a "postmodern string band", Sankofa Strings. During that same time period, Giddens was also a regular caller at local Contra dances and featured in a Celtic music band called Gaelwynd. Later in 2005, after both Gaelwynd and Sankofa Strings had released CD albums, Giddens and Flemons teamed up with other Musicians and expanded the Sankofa Strings sound into what was to become the Grammy winning Carolina Chocolate Drops.