[1][2] When Mason was five, he and his family moved from Tarrytown, New York to West Tisbury, Massachusetts, on the island of Martha's Vineyard.

This included solo acoustic recordings of "Live It Up", "Hard Hand to Hold", "Waiter at the Station", "Not Lie Down" and "Oxygen".

Mason's popularity rose after Sean Foley, an associate of musician Conor Oberst, discovered his music on a local Martha's Vineyard radio broadcast.

[3] After many live appearances throughout 2004 and 2005, culminating with a performance at the Glastonbury Festival, Mason took time off and returned to his family's home on Martha's Vineyard.

He began writing new songs and put a band together, featuring Nina Violet on viola and backing vocals, and Zak Borden on mandolin.

1, a compilation album of music from Martha's Vineyard, and was released on June 29, 2007, to help purchase transmitting equipment for WVVY-LP, a new community radio station.

He also featured in "No Room For Doubt", from Lianne La Havas's EP "Lost & Found" (and subsequently her debut album Is Your Love Big Enough?

[4] In September 2015, Mason toured Australia as a member of the ensemble cast of "A State of Grace", a themed concert featuring the music of Tim and Jeff Buckley.