"Left This Town" by Josh Thompson is a song about feeling trapped in a small town and the desire to leave but lacking the courage to do so. The lyrics describe how the town's roots are ingrained in the ground and how no one ever seems to leave. The singer reminisces about watching a friend leave town and feeling envious of their desire to explore and find something more. The song also touches on the idea that leaving a place doesn't necessarily mean leaving behind people or memories. Ultimately, "Left This Town" is a reflection on the feeling of being stuck and the urge to break free and explore the world beyond the town's borders.