Meaning of "Roll On" by Josh Ritter

"Roll On" by Josh Ritter portrays the emotional complexity of moving on from a past relationship. The lyrics reflect the inner conflict of wanting to explore new opportunities and places, while also dealing with the lingering thoughts and emotions tied to the past. The West symbolizes a new beginning, a fresh start, and the unknown, contrasting with the familiarity of the East where the former partner resides. By acknowledging the need to let go and allowing their former partner to find happiness without them, the singer ultimately expresses a sense of acceptance and understanding. The act of "rolling on" embodies the idea of moving forward, even if it means leaving things behind. The lyrics capture the bittersweet realization that sometimes, in order to grow, one must let go of the past and find their own path.