He began writing songs and performing locally in 1980 before moving to Boston to attend the Berklee College of Music[1] from 1983 to 1987.

[3] He formed the band Stump The Host[1] with fiddle player Tom Murray and singer Diane Christiansen in 1988.

By the early 1990s, Stump The Host expanded to include bassist Dave Gay, guitarist Brian Dunn, and drummer Leslie Santos and signed a songwriting contract with PolyGram Music.

[6] Dolly Varden was formed in 1994 with Dawson and Christiansen singing and writing songs, joined by drummer Matt Thobe and bassist Lisa Wertman.

After the release of Forgiven Now, also produced by Jones in Nashville, in 2002, the band took a hiatus and Dawson began focusing on solo projects.