Dylan Raymond

Dylan Raymond

Dylan Raymond, ’16 knew the importance of music at a young age. Growing up in a musical family, the Sycamore alumnus watched his paternal grandfather, Jerry Fagg, play music on the guitar, mandolin, and banjo. Fagg was inducted into the Wabash Valley Musicians Hall of Fame, and Raymond spent much of his childhood listening to his grandfather’s musical stylings.

At eight years old, Raymond decided he wanted to try playing music, and he picked up an electric guitar. He and his family listened to a variety of musical styles: old-school country by artists like Alan Jackson, the heavy rock beats of Metallica, and everything in between. Raymond took many childhood music lessons, and he began playing in numerous pop, rock, and metal bands as he grew older.

Even so, Raymond never imagined that one day he would play on a stage for fans who knew his original songs and perform with headliner country music artists.

But that’s exactly what happened. On Friday, August 26, at 7 p.m., at Terre Haute’s The Mill, Raymond will open for country music singer and songwriter Jake Owen. Owen, known for the hit singles “I Was Jack (You Were Diane),” “Barefoot Blue Jean Night,” “Down to the Honkytonk,” “Made For You,” and “Homemade,” has been an inspiration for Raymond.

The Terre Haute native has always admired the storytelling in Owen’s songs. Now, Raymond is excited to share a stage with the artist.

“I’ve always been a fan of Jake. It’s going to be fun performing at The Mill, where I get to come back home and play for people who have known me since I was a kid,” Raymond described.

A music career wasn’t always Raymond’s plan. He earned a bachelor’s degree in elementary education from Indiana State. Following graduation, he taught for one year and also served as an intervention teacher at Terre Town Elementary. Raymond’s students knew about his passion for music, and he frequently brought his guitar into class to perform.

But throughout his teaching, Raymond still played and wrote music. It was a passion, and his peers were impressed with his talent. Before he accepted a third-grade teaching position at Terre Town, Raymond was encouraged by his colleagues instead to pursue music as a full-time career. He was advised that if the performance career didn’t work out, he could return to teaching—but they believed he could “make it big” as a musical artist.

“Sometimes, you need to see that people believe in you before you take that next step in following your dreams,” Raymond said. “I’m lucky I have always had supportive family and friends.”

Visiting Nashville, Tenn. is the ultimate dream for country music artists, and Raymond has been fortunate to spend plenty of time in Music City. Raymond’s journeys included collaborative songwriting sessions, performances at bars in Nashville’s iconic Lower Broadway strip, and networking opportunities.

Today, he travels back and forth between Indiana and Nashville to work on music. Raymond eventually may call Tennessee his permanent home.

“If you want a dream so bad, you have to work for it,” he said. “I know I always have my support system back home in Indiana.”


Raymond describes his music as ‘90s honky-tonk country mixed with today’s current trends. With his signature baritone voice, he pays homage to the country music he was surrounded by as a child while also focusing on telling stories.

“From love songs to break-up songs and then songs about family, I try to have a ‘hook’ and put a different spin on perspectives you typically hear in country music,” Raymond explained. “It’s fun that I get to write and record music as my job. We’re just having a lot of fun.”

The artist has released numerous singles, including “I Can Be That,” “Gone,” “Home to You,” “More Than a Tailgate,” and “No Place I’d Rather Be.” Raymond has been known to tell personal stories in his songs. This is true in “Truck Key,” a song about his late grandfather, Richard Bryan.

One Christmas, Raymond’s grandmother gave him a key to his grandfather’s 1989 Chevrolet pickup truck. Raymond remembers riding in the front seat with his grandfather—his best friend—as they drove on remote gravel roads outside Terre Haute. The truck key is one of Raymond’s most cherished possessions, and so he wrote “Truck Key” to honor his grandfather.

“Every song tells a story,” Raymond remarked.


Now, Raymond travels across the Midwest to perform shows at festivals and other venues. He has shared the stage with popular performers, including Trace Adkins, Walker Hayes, and Russell Dickerson. Raymond said he enjoys engaging with his fans at every performance.

“I’m a high-energy performer on the stage,” he said. “It always blows my mind when people know my songs and they’re singing along with me. That’ll never get old.”

Friday’s show at The Mill has been a long time coming for Raymond. After years of forming connections, receiving rejections, and building a following on social media, he is excited to perform at a venue that has been on his bucket list since it opened last year.

As for his future in music, Raymond said he cannot predict where his journey ultimately will lead. However, he’s confident he will continue producing music and experimenting with his sound. He’s living out his dream, and he hopes his music can inspire others—especially children—to pursue their own dreams.

“If you have a dream, go for it. You never know what might happen until you try,” he reflected.

Raymond isn’t stopping anytime soon. But no matter where he goes in his career, he will remember his hometown roots and the community that supported him from the very beginning.