Life on the road is much better with another talented musician by your side. Jeff Shepherd, of the Jailhouse Poets, has navigated the rural hillsides of the Southeast, climbed the mountains of the West, and stood on the edge of the Grand Canyon with girlfriend and former Charleston bohemian rock and soul singer Rachel Kate Gillon, a.k.a. Rachel Kate. The Chicago-based country crooner and now-Nashville folkstress headed out last September and have been traveling and touring together for a little over a year. “She’s an incredible singer, and it’s beyond awesome being on the road with not just yourself, because it gets lonely,” says Shepherd.

For both Shepherd and Gillon, a lot of inspiration has come from their coast-to-coast adventures, which have been full of unexpected encounters, awe-inspiring moments, and hardships. One of those hardships involved both Gillon’s car and Shepherd’s van breaking back-to-back. “The Honda Civic started making different noises and shaking, and if you went 55 miles an hour, it would swerve out of control, but if you went 80 miles an hour, it was perfectly fine,” Shepherd recalls. “So, we went along with that until it started making a new noise. Turns out, it was definitely not OK. We pooled all our money together to get it fixed, and then my van died right after that.”

There have been spectacular moments that made every second worth it. While in Fort Collins, Colo. last December, Shepherd and Gillon stayed with some friends in a mountain house. In the morning, there were about 40 deer in the yard, and they came into the garage and let everyone pet them. Then, the duo got to experience the Grand Canyon in all its breathtaking glory after playing a show in Arizona. “There are pros and cons to living on the road, but I love it. I’ve met cool people all over — other musicians, strangers, funny old people outside of the bar — and there’s never a dull moment,” says Shepherd.

Though they travel together and harmonize on stage, Shepherd and Gillon are two separate acts, and they each have a side project. Shepherd began his musical journey with Americana group the Jailhouse Poets in Chicago, with Shepherd on vocals and guitar, Mickey T. Craft on bass, Marco Sassman on banjo and vocals, Colleen Alvin on fiddle, Matt Patterson on steel guitar and vocals, and Ben Standage on drums. Many of the members met while playing separate gigs around the city, from full-band shindigs to solo-acoustic performances. Now dubbed Jeff Shepherd and the Jailhouse Poets, the band still plays together in Chi-town on occasion.

Not only did Shepherd’s music career take off in Chicago, but that’s also where he met Gillon — at a bar called Reggies. “We would see each other playing the same music festivals here and there, and we had mutual friends. After that, we decided to go on a week tour, and we just never stopped,” says Shepherd.

Just recently, Shepherd and Gillon have started writing together. By recounting stories about people they’ve met on the road, they’ve created songs under the umbrella of a shared adventure. “We write songs about people that we’ve met, stories people have told us, friends of ours — just people,” says Shepherd.

Those stories take shape according to the atmosphere. “If it’s just me, I tend to write slower songs, because it’s just me. When I’m with Rachel, the band, or whoever, I write and play accordingly. With the full band, it’s more punk-rockish, and when it’s a solo thing, it’s slower, more country-esque, sadder songs,” says Shepherd.

Shepherd’s recent solo disc was tracked in January and March in Knoxville, Tenn. by another Americana name, Matt Woods, at Shed 55 Studios. Bringing things back to the Windy City, Shepherd met Woods while the latter was recording a podcast on Outlaw Radio Chicago a few years back. “We got thrown on a couple of shows together in Michigan and Iowa. We spent that weekend together and hit it off and became buds,” says Shepherd.

The new disc doesn’t yet have a title, but Shepherd’s leaning toward a self-titled prospect. The recording process for the as-yet-untitled record was completely different for Shepherd. A studio group was compiled, and Shepherd had to teach the players his songs. “It was an interesting and different approach. I’ve never really made a record that easily,” says Shepherd. A vinyl pressing is in the works, but that’s still a ways off.

Meanwhile, Shepherd will still be on the road with Gillon. For the Charleston show, Shepherd will be playing a solo performance, and Gillon will be joined by a full band. The two will then go on to play a festival in Gainesville, Fla. on Halloween weekend, along with Matt Woods. The annual music fest takes over almost every bar in town and draws in hundreds of musicians. As for Halloween costumes, Shepherd’s trying to convince Gillon of a particular couple outfit. He says, “I want us to be Leia and Skywalker. It’s the nerd in me, you know, Star Wars things.”

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