Hitchhiking Highway 61: A Bob Dylan Inspired Podcast

In this episode of Hitchhiking Highway 61, we take a deep dive into Bob Dylan’s “North Country Blues,” a haunting narrative about life in a failing mining town and the quiet weight of staying put. From its roots in Woody Guthrie–style folk storytelling to its echoes in later songs by artists like Bruce Springsteen and Pearl Jam, “North Country Blues” explores working-class struggle, economic decline, and the slow passage of time.Along the way, I reflect on small towns, missed chances, fate versus free will, and what it means to watch life from behind a window instead of stepping through the door. Beneath its surface as a protest song, “North Country Blues” becomes something more universal—a meditation on memory, aging, and the choices that shape who we become.

On this episode of Hitchhiking Highway 61, Kevin Fallon explores Bob Dylan’sOne Too Many Mornings from The Times They Are A-Changin’. Dive into Dylan’s imagery of distance, choices, and reflection as he captures the bittersweet pain of love and missed opportunities. This episode highlights the song’s themes of perspective, crossroads, and the ripple effects of small “what if” moments.

Join host Kevin Fallon on Hitchhiking Highway 61 as he dives into Bob Dylan's 1964 classic With God On Our Side. In this episode we explore Dylan's take on history, morality, and the heavy intersection of religion and war. We examine how Dylan questions whether any country, or person, can truly claim God is on their side. Along the way, he shares his own perspective as a history teacher and fan, connecting Dylan's words to both past and present dilemmas.

What happens when “The Times They Are A-Changin’” meets a world where nothing changes at all? In this episode of Hitchhiking Highway 61, we leave behind Bob Dylan’s anthem of progress and step into the bleak, haunting story of “Ballad of Hollis Brown.”Dylan paints the picture of a desperate farmer on the edge of survival — and forces us to wrestle with timeless questions: poverty, despair, choice, and the cycles of history that never seem to end. Is Hollis a victim? A villain? Both? And what does his story reveal about the struggles we still face today?Join us as host Kevin Fallon explores Dylan’s storytelling, the relentless rhythm of the song, and the uncomfortable empathy it creates. Along the way, we’ll reflect on why Dylan’s music still matters, why “nothing new under the sun” feels truer than ever, and what it means to notice the Hollis Browns around us before it’s too late.

On November 22, 1963, President John F. Kennedy was assassinated in Dallas, marking a cultural turning point that shattered America’s postwar optimism and ushered in the turbulence of the 1960s. In this episode of Hitchhiking Highway 61, host Kevin Fallon explores Bob Dylan’s The Times They Are A-Changin’ — an anthem written before Kennedy’s death but one that eerily captured the nation’s shifting mood. From civil rights to Vietnam to the rise of counterculture, Dylan’s stark folk declaration became the soundtrack to a decade in motion.