"The Crossing," featuring Tim on lead vocals, mandolin, fiddle, bouzouki, guitar and mandola, is a natural musical and personal intersection for O'Brien. "Since hearing Kevin Burke fiddle 'The Sailors Bonnet' on an Arlo Guthrie record in 1973, I've sought out traditional Irish music whenever and wherever I could. Old-time and bluegrass music share a common repertoire with Irish music, and the two worlds have greatly influenced one another, particularly since the 50's and 60's folk revival," says O'Brien. Like many Irish-Americans, Tim has taken a recent interest in his Irish roots, tracing back to his great-grandfather Thomas O'Brien, from County Cavan, who came to America in 1851.

The album's opening track, Ireland's Green Shore, originally from a Hammons Family Smithsonian Folkways recording, is an excellent example of the marriage of Scots-Irish and Appalachian music. Maggie Hammons' version is a cappella, reminiscent of Irish "sean nos" ("old style") singing. Bluegrass legend Ralph Stanley recorded it as a waltz. Tim has made it his own, adding the high lonesome sounds of Stuart Duncan, Del McCoury and "low lonesome" sounds of Edgar Meyer (bass) and Kenny Malone (percussion).