Hitting the Road

HTR Episode 38: Dillon Carmichael


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This week on Hitting The Road, we sit down with country artist Dillon Carmichael for an honest conversation about roots, resilience, and staying true to who you are in a changing music industry.

Raised in rural Kentucky and shaped by a deep love for traditional country music, Dillon carries forward a legacy while carving his own path. As the nephew of country icons John Michael Montgomery and Eddie Montgomery, he grew up surrounded by music—but success didn’t come handed to him. In this episode, Dillon opens up about the grind of building a career, the pressure of expectations, and the importance of authenticity in both songwriting and life.

We talk about his journey from small-town Kentucky to the national stage, the stories behind his music, and how he balances honoring country music’s past while pushing forward with his own sound. Dillon also shares perspective on perseverance, faith, and what it really takes to last in a business that’s always evolving.

Whether you’re a longtime country fan or someone chasing a dream of your own, this conversation is full of real-world insight and encouragement you won’t want to miss.


Check out Dillon’s music - https://dilloncarmichael.com/

Check out our sponsor - https://nashvillevans.com

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Hitting the RoadBy Sponsored by Nashville Vans