Where he first picked up his grandfather’s guitar. It’s where he watched his family play music, at a friend’s house with a stage built into the living room. Simpson, 41, moved away from this stretch of Appalachia when he was 7, but its ethic and spirit remain bone-deep in him. But the coal industry’s decline has left things precarious, and he’s been thinking through ways to meaningfully offer help. “Musically speaking this is the most culturally rich pocket of American existence outside of jazz,” he said of the region where bluegrass was forged. He went to the White Flash diner on Main Street, ordering two cheeseburger sliders and fries, almost sneaking out unnoticed before signing a pair of guitars for the owner and his son. He drove up to Hillcrest Drive, where he and his parents used to live in a prefab home, then picked up his cousin Brad in the McDonald’s parking lot before heading to his family graveyard, which sits on High Top Mountain, which he named his first album after six years ago. How many Grammys do I need, right?” he asked from behind the wheel of his black Subaru WRX STI. Just before the intersection, a small sign announced that he was in the right place: “Hometown of Grammy Award Winning Artist Sturgill Simpson.” This was the way into Jackson, the sparse, hilly town of around 2,000 people he grew up in.

Earlier this month, Sturgill Simpson headed eastward from Lexington until he hit Highway 15, which he drove until it dead-ended into Highway 30.

Simpsons hit and run no music fix