"Over The Hill" is a song by John Stewart about a person who is tired of the same old routine and is seeking a change. The lyrics describe the protagonist slipping down a back road and running towards the unknown. They are searching for something more meaningful in life, and the metaphor of chasing a moving train represents the challenge of finding fulfillment amidst life's uncertainties. The chorus, "It's over the hill," suggests that the person has come to a critical point in their search, where it's time to take a leap of faith and continue moving forward. The phrase "second wind" represents the renewed energy and determination to keep going despite the obstacles. Overall, the song is about the journey towards self-discovery and finding one's place in the world. It's an anthem for those who are willing to take risks and embrace the unpredictable nature of life in pursuit of their dreams.