Skip Cherryholmes

Stand-out Bluegrass musician @skipcherryholmes, who lives in Raleigh, N.C., is our Lead Dad of the Week.

Skip, a guitarist and singer, started touring with his family’s band Cherryholmes when he was still in middle school. After a decade, he went out on his own with the band Sideline Bluegrass, which at its peak was playing some 140 shows a year.

“When 2020 shut everything down, that was the most time I had to be a husband and a father,” he said. “It was the most consecutive nights sleeping in my own bed since I was a pre-teen. The adventure of being a father spoke to me.”

The following year their second child was born. “That was when I first started feeling I didn’t need to be gone so much.”

He had been performing with his father-in-law, Steve Dilling, another Bluegrass great. (Skip met his wife Stephanie when their families were on tour together.) And that time with his wife and children – not to mention in his own bed, not our a tour bus – was an inflection point for him.

“Last August 2022, my son came to me and was talking to me about something that was important to him, but I couldn’t hear a word he was saying,” Skip said. “All I was hearing was the muddle of the road. I stopped myself. I couldn’t do it to him anymore. I’m gone 200 days a year, and even when I’m home I’m not present. That’s setting a bad example for him. I needed to get off the road.”

While not entirely sure what he’s going to do next when the band comes off the road for good this month, Skip knows one thing for sure: he’s ready to embrace being a Lead Dad and pivot his career to be home more with his family.

“It’s emotional for sure,” he said. “I’ve run into hundreds of thousands of people who have said that my music took them out of what they were dealing with. I thrive on that. But parenting to me is the most brilliant and overall amazing experience – if you’re blessed enough to have that, you should pour everything into it.”

We commend Skip for making what was surely a tough choice. We’re confident his next chapter will be just as interesting and rewarding.

Check out his music here: