Bourbon, Bluegrass, and a Bit of Serendipity

Every good road trip has a rhythm. Ours started in Chicago, rolled through Kentucky, and landed in the music capital of the South: Nashville, Tennessee. But the real magic wasn’t just in the destinations—it was in the curious questions, the Google rabbit holes, and the shared laughter with my road partner, Nicole.

The Journey South

We left Chicago buzzing with road trip energy and made our way through the rolling landscapes of the Kentucky Bourbon Trail. Between distillery stops and scenic drives, we detoured into Mammoth Cave National Park—the world’s longest known cave system. Walking through its vast underground chambers felt like stepping into another world, a quiet pause before the excitement of Nashville.

When you spend that much time on the road, the conversation meanders as much as the highways. I shared with Nicole the kinds of odd facts I have looked up on solo trips: why some roads in South Dakota and Minnesota are red (it’s the iron-rich gravel mixed into the pavement), or what crops stretch endlessly across the Midwest. Travel teaches you a lot—but Google is often the co-pilot. This time, Nicole took over some of the searching duties, and soon we had a running list of curiosities to explore.

Chasing Bluegrass in Kentucky

Somewhere along the Kentucky backroads, I confessed I’d always wondered about the origins of bluegrass music. My guess? The first band must have come from Kentucky—after all, the state is famous for its rolling fields of bluegrass. Nicole did some quick digging and uncovered the truth: the genre takes its name from Bill Monroe and the Blue Grass Boys, a band formed in the 1930s in Rosine, Kentucky. Monroe named the group after the bluegrass of his home state, and today he’s honored as the “Father of Bluegrass.”

Little did we know how perfectly timed that bit of trivia would become.

Nashville Nights at the Grand Ole Opry

Our friend Lena suggested we catch a show at the Grand Ole Opry while in Nashville. The band on the bill? Brothers Comatose—a fun, lively group I’d first seen years earlier at aOgden music festival in Utah. It felt like the perfect full-circle moment: friends, music, and an iconic venue.

We bought tickets, brushed up on a few of their songs, and caught an Uber to the Opry. Our seats were classic nosebleed benches, but the energy was electric. To our surprise, the evening wasn’t just a Brothers Comatose concert. It was a special tribute to Bill Monroe himself, part of the “100 Opry” series celebrating a century of performances at the venue. Several bands took the stage, weaving together stories, fiddles, and harmonies that carried the history of bluegrass forward.

It felt like stepping into a time capsule—part TV variety show my grandparents would’ve loved, part modern jam session. And just like that, our random road trip curiosity about bluegrass had come full circle in the most serendipitous way possible.

Final Notes

Road trips are made up of more than destinations. They’re about the questions you ask along the way, the music you stumble into, and the memories you piece together with the people riding shotgun. For us, this one was bourbon, caves, and bluegrass—and it ended with a fiddle tune echoing through the halls of the Grand Ole Opry.

Nashville, TN