In 1999, Marty Stuart changed the course of his career — and, arguably, the upward trajectory of Americana — with the past-honoring concept album The Pilgrim.

Stuart’s pivot from chasing radio hits found him recording a love letter to the founding mothers and fathers of country and bluegrass music with the likes of George Jones, Johnny Cash, Emmylou Harris, Pam Tillis, Ralph Stanley, Earl Scruggs and Dobro legend “Uncle” Josh Graves. To retrace a transformative journey back to his musical roots and prove to young songwriters that following your heart pays off in the long run, Stuart has been revisiting The Pilgrim, first through live performances and now with the album’s first-ever vinyl release, out Friday (Oct. 18).

As teased in the final episode of Ken Burns’ Country Music docu-series, the 1996 death of Bill Monroe challenged Stuart to rethink his career goals amid one of country music’s most fiscally successful decades. The Pilgrim's title track is a direct response to that pivotal moment.

""The Pilgrim" song, actually, I wrote when Bill Monroe died,” Stuart tells The Boot. “I was in Sun Records in Memphis, and I got the word that he’d passed away. They asked me to come home and play in his service. I thought, ‘Time out.’ I went walking around the streets of Memphis and wrote that song. It’s the only song [on the album] I had for three years, but I knew I it was a cool song, so I hung onto it.”

The next step in The Pilgrim’s journey came when Stuart consulted Ricky Skaggs, a childhood friend who’d already unplugged and gone back to his bluegrass roots, during a Sunday morning service at the First Baptist Church of Hendersonville, Tenn. “I was in Lester Flatt's band and I was in Johnny Cash’s band, and both of those guys had long, long, long since gone down those roads. They were miles and miles down that road,” Stuart reflects. “I knew what I had to do, but I wanted to talk to someone who had recently done it and say, ‘Is the water still clear?’ Ricky was that person.”

Church fellowship plus a real-life story of love and redemption from Stuart’s hometown of Philadelphia, Miss., involving “cross-eyed” Norman and local beauty queen Rita, inspired Stuart to write songs to go along with “The Pilgrim.” When it came time to celebrate the album’s 20th anniversary, Stuart and his team began reconsidering material left on the cutting room floor, including the recently completed song “Even Trains Have to Cry,” as bonus tracks.

“I can’t swear to this, but I think what I did was I had kind of a shootout between ["Even Trains Have to Cry'" and "Hobo’s Prayer,"” Stuart recalls. “I thought "Hobo’s Prayer" was maybe a little better song or fits the project better. Eighteen years down the line, I looked at "Even Trains Have to Cry" and went, ‘That needs to be finished.’ I put the last verse together.

"[My band] the Superlatives did it one time on our TV show," he adds, "and I thought, ‘That’s a pretty good song.’ That’s why it made the record."

In addition to the 20th anniversary vinyl release of The Pilgrim, with a gorgeous gatefold cover, Stuart also put together a book titled The Pilgrim: A Wall-to-Wall Odyssey, out Nov. 12 and featuring a CD of the original album plus bonus material. Of his plans, Stuart explains, "I thought The Pilgrim was a project that deserved more than just a casual re-release."

"It was a deep work. It was a work that came from the heart," he reflects. "I also wanted to dig down deep inside myself and relive it and hand it out there for young artists that, someday they’ll come upon that thing that the system’s going to let them down, and they’re going to need to go to their heart.

"There’s a price to pay for [going to the heart], but it’s okay," he adds, "because it’s been done before.”