David Stewart: The Walking Cowboy Rides Again


David Stewart: The Walking Cowboy Rides Again

by Emerald Butler

“I’ve always loved music from the time I was a child,” David Stewart shares at the beginning of a conversation about his life, music, and stories of restoration. “I think anyone can learn how to play an instrument, but to have a passion for it, I think you have to be born with it.”

David says that he wasn’t born into a musical family, but his parents did own a tavern in Bradenton, Florida that had a dance hall. The Village Barn was home to a lot of music and square dances. “I started playing when I was about 10 years old pretending that I was on the stage of the Opry. About the age of 13, I had an uncle that would take me down to a local tavern, sneak me in, and I’d play for the people in the afternoon. He’d put a tip boot out, but I think he got more of a cut than I did,” David chuckled. “I was exposed to music when I was a young child because there was music all around me, and I think that’s what got me to loving music.”

When David grew old enough to where he didn’t have to sneak into the club, he became the club’s house band and began opening acts for a lot of artists who came out from Nashville. 

“I went to Nashville in the early ’70s and was trying to be an artist, but it just didn’t work out for me. Then I moved to Wyoming in ’77. In 1988, my wife and I were sitting at a truck stop one night. I was humming a song I wrote called ‘In the Wings of the Grand Ole Opry’ and my wife asked me what I would do to sing on the Grand Ole Opry. I told her ‘I’d walk to Nashville if I could sing on the Opry’, and she said, ‘what a great idea!’ So, I did that. It was a 1600-mile walk. I had no contact with the Opry at all. My whole deal was that I was going to walk there and ask them if I could play.

I didn’t know if I could make the trip, but I wasn’t going to talk to them until I made it there and let them know how much I cared about the Opry.”

As David was making the journey, a truck driver stopped and asked David if he was the “walking cowboy”. David said yes, and soon after he went viral in 1988 via the CB radio. “I got a lot of press out of it. A lot of people were writing to the Grand Ole Opry and told them to let me play. It was fortunate that I didn’t have to ask them; they asked me.” David shared that every day of the journey presented difficulties reaching from heat and drought to emotional struggles and homesickness. “Being away from my family was probably the hardest part of the trip. It was emotionally draining. I would call home from a payphone once or twice a week.  Towards the end of the trip my wife came out

the last 100 miles and she walked a day or two with me. Most of the time I had a guy named Floyd Hayes who was my support and did some PR for us. He had a little camper and he’d go ahead of me and he’d have some gig lined up for me where we could make a little money for gas. It was a pretty grueling trip. I lost 32 pounds, but when I got there my legs were like concrete. I used to sing a song by Cristy Lane called “One Day at a Time” and that’s what I thought about because the world goes slow when you’re walking. I tell people now if you want to learn patience, walk across the country. My motivation was just to put one foot in front of the other and keep going.”

“Jambalaya” for the crowd. “I remember it like it was yesterday,” David shared. Soon after, David became friends with Eddie Raven and began writing songs for the singer. “Eddie called me because he had heard some of my songs, and he asked me if I would write for his company, and then he cut some of my songs for his album ‘Living in Black and 

White’. He was always encouraging me, and when he decided to cut a grass album, he came to me. He also got me the Tanya Tucker cut called ‘I Can Do That’.” Over the years, David has written a lot of country and bluegrass songs. Although David got some great cuts in the Nashville writing and recording community, he confessed that he prefers writing at home with friends as opposed to writing in a company room in Nashville with a stranger. As the Nashville music and scene began to change, life started going in another direction for David.

“I was digging a ditch. I got eat up by mosquitoes that night, and the very next day I began going downhill and getting very sick.”

It was in 2000 when David caught the West Nile virus. “It just started ravaging my body. I was losing weight, and I was very, very ill. There was no cure for it at the time except for the good lord. The doctors all thought I was going. My vital organs were beginning to shut down. With a high fever, it started going into my brain, and it attacked my nervous system. I don’t know why I recovered.  After I recovered, I stuttered for a while, my hands shook, and I had memory loss. I had to relearn the guitar, and I didn’t think I would ever write again. Over the whole period, I probably lost about ten years of music.” David credits his wife for his care and his restoration of his musical abilities. Jackie would turn on David’s recordings to help him relearn his songs. “She’s always been supportive of my music because she knows it’s always been a dream of mine.”  David’s music, however, isn’t the only restoration project that the couple has taken on.

“There was a lady by the name of Dawn Dawson who bought The Occidental when it was about 8 weeks from being torn down because it had been closed for a few years.”

The Occidental is a historic hotel and once upon a time brothel in Buffalo, Wyoming that was built in the hay day of the old west. The hotel has hosted legends like Calamity Jane, Butch Cassidy, and Teddy Roosevelt.

“Dawn started the renovation on it. She had a real keen eye for history, but she was not a very good manager of things, so she ran into financial trouble. In about 2004 we got involved with her and my wife Jackie said, ‘we need to help her’. I said I didn’t know how, and Jackie said ‘your music. If you play your music, people will come.’ So, I started a jam session here at The Occidental on Thursday nights and it’s been going for 15 years now and we’re packed every Thursday night.” After a few years of buying stock in the Occidental, David and Jackie bought out the whole thing in 2011 and became the sole owners. The couple hosts guests from all over the world, and the music has become a great community connector.

As the couple takes care of day to day upkeep and musical performances at The Occidental Hotel, David continues to write songs of tradition and meaning. Lorraine Jordon & Carolina Road’s 2020 single “Bill Monroe’s Ol’ Mandolin” is just one of David’s latest cuts. Over the past few years, David has had a slew of chart-topping bluegrass cuts. David shared that he is very excited for Carolina Blue’s upcoming August 7th single and video release of his song “Too Wet to Plow” that he wrote while sitting in his home at The Occidental Hotel. David is also awaiting two other releases of his cuts with Lonesome River Band and Fast Track. David’s advice to others is to “keep following your dreams.”

Needless to say, David Stewart has had a very exciting and eventful life from playing the Grand Ole Opry to surviving a deadly virus. He has seen, walked, and written for miles and miles, but it almost seems like the “walking cowboy” is only getting started, or one could say that the “walking cowboy” rides again.