Tyler Childers headlines Friday, July 18, at FairWell Festival. (Sam Waxman)

The Bluegrass State spawned several artists playing FairWell Festival, including Simpson, Childers and Yoakam

For decades, the Commonwealth of Kentucky has punched above its weight when it comes to producing musicians.

The Western part of the state boasts not only the inventor of bluegrass music, Bill Monroe, from Rosine, but also one of the pioneers of progressive bluegrass, Sam Bush from Bowling Green. The early country music star Merle Travis was from Muhlenberg County — also the birthplace of one of The Everly Brothers, and a place of deep roots and inspiration for the great songwriter John Prine.

Kentucky’s largest city, Louisville, produced jazz giants Lionel Hampton and Marshall Allen, seminal post-rock band Slint and contemporary folk singers Will Oldham and Joan Shelley. The second-largest city, Lexington, is the hometown of punk legend Richard Hell, current country star Chris Stapleton, noise band Hair Police and … 40% of the Backstreet Boys!

But it’s the easternmost third of the state whose musical family tree truly boggles the mind. Marked by the hills and valleys of the Appalachian Mountains and once home to a bustling coal-mining industry, Eastern Kentucky’s roster of native artists reads like a who’s who of country, folk, bluegrass and old-time music: Keith Whitley and The Judds from Ashland. Loretta Lynn and Crystal Gayle from Paintsville. World-class mandolinist Ricky Skaggs from Cordell, country singer Patty Loveless from Pikeville, songwriter extraordinaire Tom T. Hall from Tick Ridge and the mother of traditional folk music, Jean Ritchie from Viper.

If ever you need evidence that a combination of hard livin’, front-porch pickin’ and church-choir singin’ turns ordinary human beings into extraordinary musicians, you’ll find it here.

Of course, you’ll also find it this weekend at the FairWell Festival in Redmond, approximately 2,400 miles from Loretta Lynn’s famed homestead in Butcher Hollow. Now in its third year, FairWell is a large-scale country music festival run by a multinational corporation that, ostensibly, draws its on-stage talent from all across the United States and beyond.

But for those who pay attention to such things, it’s hard to miss that three of the four top-billed artists at the 2025 version of FairWell originally come from an area of Eastern Kentucky that’s about the same size as Jefferson County. (The fourth, by the way, is Sierra Ferrell from Charleston, W.V., just a few hours to the east.)

You can draw a sharp isosceles triangle connecting the hometowns of Friday’s headliner, Tyler Childers; Saturday’s headliner, Sturgill Simpson; and Dwight Yoakam, who will play just before Childers on Friday. The first two are among the most popular figures in the surging non-mainstream roots-music scene, while Yoakam, at this point, is a legend of country music, four decades into a distinguished career.

It’s worth noting that while they come from the same area, they don’t sound the same. Childers, from Lawrence County, plays bluegrassy folk songs and sings as vividly as anyone alive about love and life in the Appalachian region. Simpson is a relentless iconoclast from Breathitt County who has made a career out of shapeshifting — from psychedelic country to classic rock to bluegrass and beyond. And Yoakam, from Pike County, is a longstanding neo-traditionalist and a giant of country music’s famed Bakersfield sound.

Together, they’ll make for a deliciously varied couple of evenings at FairWell — a festival with, this year, a distinctly Kentucky flavor.

If you go

What: 2025 FairWell Festival
When: Noon-10 p.m. Friday, July 18
Noon-11 p.m. Saturday, July 19
Cost: Two-day tickets start at $289, one-day tickets start at $139
Where: Deschutes County Fair & Expo Center, 3800 SW Airport Way, Redmond
Cost: fairwellfestival.com