Dick Curless was a singer/songwriter born in Fort Fairfield Maine. He hosted a radio show in Massachusetts. His music career didn't really take off until 1965 when he recorded "Tombstone Every Mile."  The song put Dick on the country music map and even made it to the top 5 on the Billboard Country Charts.

The song (written by Dan Fulkerson) is about one of the most dangerous stretches of road in Aroostook County. The "Haynesville Woods" that's mentioned in the song refers to an area in Hanesville, Maine where there is a hairpin turn in the road that caused truckers to crash being unable to navigate the turn.