SteelDrivers Beat Rocky Road

It was a scorching Labor Day weekend, 1980, and bluegrass musician Mike Fleming was broken down on the side of a dusty Kansas road.

Tractor-trailers rolled by. Steam leaked from his band’s overheated van. There was no help in sight.

In that moment, Mr. Fleming grew up.

“You know, I think it’s time to try something else,” he remarked to mandolin player Mike Henderson. “There’s something better than what we’re doing out here.”

When they returned home to Missouri, they parted ways.

“Boy, I forgot about that until just now,” Mr. Fleming reminisced last week during a telephone interview, his baritone voice dripping in a southern drawl. “When you’re young, you’re fearless. And you can do just about anything.”

Like travel the Midwest in a 15-seater van with nothing but a dream. One he thought had died in Kansas. He was wrong.

Nearly a decade later, his telephone rang. It was Mr. Henderson on the other end.

“You know,” he said, “you really wanna play music for keeps? You need to come to Nashville.”

He was right. There, Mr. Fleming became one of The SteelDrivers. He’s the bassist for the five-piece bluegrass band, known for its new music with an old feeling. The group will make its East End debut on Saturday, January 18, at the Shelter Island School auditorium.

“Mike said, ‘I’m puttin’ together a possible bluegrass band to play some tunes and play maybe once a week around town,’” Mr. Fleming said. “Oh lordy, so much for that. At the time, it was like, ‘Okay, that sounds good. That sounds like fun.’ I’d always liked bluegrass, even though I didn’t grow up with it. But when it hit, it hit hard.”

Mr. Fleming was, at first, a product of the British invasion. He was in sixth grade, living in Indiana, when he watched The Beatles perform on “The Ed Sullivan Show.” His grandparents shook their heads. Be went out to get himself a “gi-tar.”

It wasn’t until college at the University of Missouri—where he first met Mr. Henderson—that he fell into the music scene, with a little help from the 1972 film “Deliverance.”

“I heard the banjo and, all of a sudden, it was like, ‘What was that?!’” he said. “I got the bug. That was the start of the downhill.”

He laughed. “Playing the banjo, my IQ goes steadily down. Mike started to play mandolin and we were just like anybody else, trying to learn new instruments in an unfamiliar time of music.”

The bluegrass revival was under way. Musicians across the Midwest—Mr. Fleming and Mr. Henderson included—were learning the old tunes, he said, but also experimenting by putting traditional instruments to new songs.

That eventually became the foundation of The SteelDrivers, Mr. Fleming said, while bringing other influences into their original songs. In 2008, they dropped their self-titled debut album. And, then, everything changed.

To date, the band has been nominated for three Grammys, four International Bluegrass Music Association awards and the Americana Music Association’s New Artist of the Year.

“I didn’t realize, I had no idea at the time, that people would like it,” Mr. Fleming said. “I’m still amazed, boy, that people come to see us. That first year, it was a fun year. We had a lot of nominations and we’d always laugh that we didn’t win one of them, so, woo! And we’d all sulk.”

The awards season tested the bandmates’ sense of humor, as did the winter of 2009 and the fall of 2011, when two SteelDrivers made their exits—frontman Chris Stapleton and founder Mr. Henderson, respectively.

The devastated group could have handled it one of two ways: give up or overcome.

They chose the latter.

In 2012, British pop superstar Adele named them one of her favorite bands. She covered their song, “If it Hadn’t Been For Love” as a bonus track on her album, “21.”

In February, The SteelDrivers’s fame soared to an all-time high with the release of their third album, “Hammer Down”—featuring new lead vocalist Gary Nichols on guitar and Brent Truitt on mandolin, as well as veterans Tammy Rogers on fiddle and vocals, Richard Bailey on banjo and Mr. Henderson on bass and vocals.

Last week, Mr. Fleming said he was glad that he kept at it.

“I don’t even know how many people I talked to who had figured, this was it. We were done. ‘You can’t survive,’” the musician said. “But we did. We decided, yeah, we’d keep marchin’ on.”

The SteelDrivers will give a concert on Saturday, January 18, at 7:30 p.m. in the Shelter Island School auditorium. Tickets are $20, $25 and $30, and students receive a $10 discount. For more information or to buy tickets, call 749-0626 or visit sylvestermanor.org/event/annual-bluegrass-concert.