Prison on Route 41 Lyrics

Lyric discussion by ohnoodles 

Cover art for Prison on Route 41 lyrics by Iron & Wine

I don't think the word 'prison' should be taken completely literally, just as a bad experience, or something similar, that they're caught up in and can't escape.

maybe a family tragedy that he's blatantly ignoring with the help of Virginia?

could be way off, but that's my loose interpretation