David Stewart: A Bluegrass Heart and Wyoming Soul

When you walk into the Occidental Hotel in Buffalo, Wyoming, you can feel history humming through the walls, the kind that carries both the sound of fiddles and the quiet strength of community. Behind that legacy stands David Stewart, the hotel’s owner, a man whose life story reads like a well-worn bluegrass record, full of heart, hard work, and a deep love for people and music.

In 2024, David’s song “God Already Has” earned Gospel Song of the Year at the IMBA World of Bluegrass Awards. He was also nominated for Songwriter of the Year, marking a comeback that touched not just his career, but his soul.

“When we wrote that song,” Stewart said, “I knew immediately I wanted Dale Ann Bradley to sing it. She’s a friend, and I could just hear her voice on it. We wrote it sitting under the awning at the Blue Gables Motel, and something about that moment just felt special.”

The song’s message clearly hit home, not just for bluegrass fans, but for everyday folks looking for hope. Stewart shared how letters and emails continue to pour in from people singing the song in churches or playing it during tough times. “It’s a powerful thing,” he said softly. “It’s humbling when something you wrote helps someone else heal.”

From Florida Roots to Wyoming Mountains

Before Wyoming ever claimed him, Stewart grew up surrounded by the sweet twang of bluegrass in Florida. “I grew up on bluegrass,” he recalled. “Tony Rice, Bill Monroe, the Stanley Brothers, the Osborne Brothers, all those old timers shaped me.”

Bluegrass always stayed in his blood. “It’s in my roots,” he said. “It’s where my heart goes back to.”

The Songwriting Process: Chasing the Hook

For those who dream of writing songs, Stewart’s process is simple, but intentional. “I like to start with what’s called a hook,” he explained. “Usually that’s the title, something that sticks. Then I write around that. I’ll use a throwaway melody at first, then find one that fits the words, and make sure the lyrics and melody marry each other as I go along.”

Listening to Stewart’s songwriting process, I could tell that he has mastered his craft and there is a lot of wisdom behind his process. One phrase came to my mind listening to his advice, “the power of simplicity.” 

Advice for the Next Generation

When asked what advice he’d give to young musicians stepping on stage for the first time, Stewart’s response was grounded in wisdom: “It’s like anything else, you have to practice your craft every day. Whether it’s playing guitar, singing, or writing, you can’t just walk on stage and expect to be great. You’ve got to work at it.”

He compared it to learning a trade, no shortcuts, just steady, daily work. “Some people have natural talent, but even talent needs to be developed,” he said.

The Occidental Jam: Music as Mission

That same belief in hard work and community shows up at the Occidental Hotel every Thursday night, where the famous Occidental Jam has been going strong for nearly two decades.

It started humbly in 2006, when Stewart and his wife Jackie wanted to help the previous owner, who was struggling at the time. “Jackie said, ‘Use your music, David. Play, and people will come,’” he recalled. “So I started the jam.”

And people did come, first a few locals, then crowds that now fill the room week after week. What began as a small gathering of pickers and players has become a beloved tradition, part concert, part community outreach.

The jam has raised thousands of dollars through scholarships for local kids and support for families in need. “We pass a little can around every week,” Stewart said with a smile. “It’s more than music, it’s become a mission.”

Love, Loyalty, and The Long Walk

In his book The Heart and Soul, Stewart writes about the deep partnership he shares with his wife, Jackie. Her encouragement and faith in him have been constant, from his early days as a musician to his walk across America.

He shared the story of how that journey began in 1987, while they were sitting in a truck stop in Gillette. “George Jones was singing on the jukebox,” he said. “And Jackie asked me, ‘What would you do to sing on the Grand Ole Opry?’ I told her I’d walk to Nashville if that’s what it took. And she said, ‘Well, that’s a great idea. You should do it.'

So he did. Without social media, just grit and faith, he walked all the way to Nashville,  a journey that made national headlines as “The Walking Cowboy.” Truckers spread the word over CB radios, and before long, the story of the man walking for his dream captured hearts all across America.

“Jackie’s always believed in me,” Stewart said. “She’s been my support vehicle, literally and spiritually. She’s always seen something in my music that I couldn’t always see in myself.”

A Life Lived with Heart

After decades of writing, performing, and building community, David Stewart has seen just about every side of the music business. When asked if there’s one question he’s never been asked, he chuckled. “You know, after thousands of interviews over the years, I think they’ve covered just about everything,” he said. “But I’m still grateful every time someone wants to talk about music.”

Grateful, that’s probably the best word to describe him.

From his early days in Florida to the legendary Occidental Jam, from a long walk to Nashville to a Gospel Song of the Year award, David Stewart’s story is one of faith, family, and the kind of perseverance that keeps the soul of Wyoming music alive.

As he says it best: “It’s more than just music, it’s a mission.”