In 1988, Sexton moved to Boston, and began playing on street corners and at open mic nights around the city. Sexton released a collection of self-produced demo recordings in 1991 called In The Journey. The album was released on an 8-track cassette, and Sexton sold 15,000 copies to fans. He was given the National Academy of Songwriters Artist of the Year Award in 1994.He released an album called The American in 1998, and another album called Wonder Bar in 2000. He launched his independent record label, Kitchen Table Records, in 2001 and released a concert album called Live Wide Open. His album, Seeds, was released in 2007. In 2008, he released a second live album called Solo.Subsequent albums included Sugarcoating in 2010 and Fall Like Rain in 2012. In 2015, he released another studio album called Mixtape of the Open Road. In 2017, Martin joined Chris Anderson (upright and electric bass) and Boo Reiners (multi string instruments) to make The Martin Sexton Trio.