In the world of country music, authenticity and grit are often seen as defining traits of the genre. Few bands embody these qualities more than 49 Winchester. With their roots firmly planted in the small town of Castlewood, Virginia, the four-piece band has fought tooth and nail to carve out their place in the ever-evolving world of Americana and rock. They have worked tirelessly to reach a moment where their dreams of playing alongside some of the biggest names in country music are finally coming true.

On the cusp of joining Eric Church for his 2026 Free the Machine Tour, 49 Winchester is poised to take their next step into the national spotlight. It’s a moment that, for the band, feels like both a culmination of their hard work and a gateway to an even brighter future. Their latest album, Fortune Favors The Bold, is a testament to their growth, evolution, and undeniable talent.

When you speak with lead singer Isaac Gibson, it’s clear that this isn’t just a career milestone — it’s personal. Gibson, who grew up in Castlewood, reflects on his journey with gratitude and a deep sense of humility. “Everything we’ve done, we’ve built it from the ground up,” he says. “Nothing’s been handed to us. Every step of the way has been earned.”

The band’s story is one of perseverance, a tale of childhood friends who started playing music together as teenagers and never stopped. Formed in 2014, 49 Winchester’s early days were defined by a simple desire to make music that resonated with both the band and their community. Castlewood, with its small-town charm, may have been a place where few could imagine stardom, but for the band, it was the perfect place to develop a sound that was uniquely their own.

From the start, the band has been driven by an unrelenting passion for music. The members of 49 Winchester — Isaac Gibson, bassist Chase Chafin, guitarist Bus Shelton, and pedal steel player Noah Patrick — were all born and raised in the small, tight-knit town of Castlewood, a place that helped shape their worldview and work ethic. Despite facing many challenges and limited opportunities in their rural community, the band pushed forward with a fierce determination.

“We didn’t have a lot, but we had each other, and we had music,” Gibson recalls. “That’s how it all started, and it’s been our driving force ever since.”

In many ways, the band’s journey mirrors the themes explored in Fortune Favors The Bold. The album, which marks their debut with New West Records, blends elements of rock, Americana, and Appalachian folk to create a sound that’s fresh, raw, and powerful. But it’s more than just music; it’s a reflection of the band’s evolution both sonically and personally.

For 49 Winchester, this album isn’t just about their sound; it’s about their identity as a band. “We’ve matured,” Gibson says. “We’ve gone from a softer sound to something edgier, grittier. It’s about finding who we are as a band and embracing that.”

This evolution is evident in every track of Fortune Favors The Bold. It’s an album that refuses to be neatly labeled. One moment, it’s an alt-country anthem that would make any honky-tonk bar proud; the next, it’s a rock-driven power ballad with an Appalachian twist. The band’s willingness to experiment with different sounds while staying true to their roots has made them stand out in an industry where genres often overlap and bleed together.

But the journey hasn’t been without its struggles. As much as Fortune Favors The Bold is a celebration of the band’s growth, it’s also a reflection of the hard work that has gone into reaching this point. For years, Gibson and his bandmates worked day jobs while also playing shows and writing music, determined to make their dream a reality.

“We’ve all worked hard for this,” Gibson says. “I was a stone mason for a long time. But music was always there — it was always something I wanted to do. I think that’s what makes us different. We’re not just trying to make it. We’ve worked for it, and we’re still working for it.”

It’s that work ethic, that refusal to give up, that has made 49 Winchester a success. And now, with their partnership with Eric Church, they are about to reach an even wider audience. Their appearance on the Free the Machine Tour isn’t just about sharing the stage with one of the biggest names in country music; it’s about showcasing their own unique brand of music to a new group of fans who may not have heard of them before.

As they prepare to hit the road with Church, the band is filled with a sense of excitement and anticipation. The tour represents both an opportunity and a challenge. For 49 Winchester, it’s a chance to prove that they belong alongside the best in the business.

The partnership with Church is more than just a career milestone — it’s a testament to the band’s hard work and dedication. As one of country music’s most beloved artists, Church has long been known for his gritty, unapologetic approach to music, and his decision to bring 49 Winchester on the road is a validation of the band’s authenticity and sound.

“This tour is huge for us,” Gibson says. “We’ve been working toward something like this for a long time, and now we’re getting the chance to show people who we are and what we’re all about.”

For their fans, seeing 49 Winchester on the Free the Machine Tour will be a dream come true. For years, the band has had a loyal following, especially in their hometown of Castlewood, where they’re still seen as local legends. But now, as they take the stage in cities across the country, they’re about to prove that they’re ready to take on the world.

“It’s a long road,” Gibson reflects. “But it’s a road that’s worth traveling. We’ve built this from nothing, and now we’re here. And we’re not stopping anytime soon.”

As 49 Winchester embarks on this next chapter, one thing is clear — their journey is far from over. The Free the Machine Tour is just the beginning, and with each city they play, they’re not only earning new fans, they’re cementing their place as one of the most exciting bands in Americana and rock today. Their story is one of persistence, passion, and most of all, heart. As they continue to grow and evolve, their message remains the same: Keep going, keep pushing, and always be bold.