Railbird Festival 2025: The People, Music, Bourbon, and Kentucky Spirit

The Railbird Festival, held on May 31 and June 1, 2025, at The Infield at Red Mile in Lexington, Kentucky, delivered an unforgettable weekend of music, community, and local culture. With over 30 artists performing across three stages, a carefully curated selection of Kentucky’s finest bourbon, and a vibrant crowd, the fifth edition of this beloved festival solidified its place as a cornerstone of the Bluegrass State’s summer music scene. Despite a slight pivot toward pop-country headliners, the festival maintained its rootsy charm, drawing a slightly smaller but still massive crowd compared to the previous year’s peak of nearly 45,000 daily attendees. From electrifying performances to unpredictable weather, here’s a deep dive into the entertainment, crowd energy, weather challenges, vendors, and the overall vibe that made Railbird 2025 a memorable experience.

As always, the people were a treat, brought together by a common love of music. And bourbon.

The People

Heading to one of the many, many bars between sets, I saw two lovely ladies, and one looked familiar. As I walked closer, I was sure I recognized one, and she seemed like she knew me as well. As I approached, one of them said hello and asked if I was going to take their picture. I was, because I thought one of them was Brennen Leigh, the guitar player for Asleep at the Wheel, which she denied. We talked for a few minutes and I snapped them anyway, and again the next day with two more of their friends. The Asleep at the Wheel photo is added, just for fun.

The Entertainment: A Diverse and Dynamic Lineup

Railbird Festival 2025 boasted a lineup that blended country, Americana, folk, and roots music, with headliners Lainey Wilson (born May 19, 1992) and Jelly Roll (born December 4, 1984) commanding the Limestone Stage on Saturday and Sunday nights, respectively. The festival’s three stages—Limestone, Elkhorn, and Burl—offered a rich variety of performances, ensuring there was something for every music lover. While the headliners drew massive crowds, the daytime acts, including The Red Clay Strays, Wyatt Flores, and Sierra Ferrell, were often cited as stealing the show with their raw energy and authenticity.

Lainey Wilson’s High-Energy Headlining Set Lainey Wilson’s Saturday night performance was a masterclass in commanding a stage. The Louisiana native, known for her role in Yellowstone and her string of chart-topping hits, strutted across the Limestone Stage in her signature bell-bottoms, exuding confidence and charisma. Her set kicked off with “Keeping Up With The Jones,” setting a lively tone that carried through fan favorites like “Smell Like Smoke,” “Hold My Halo,” and her first No. 1, “Things A Man Oughta Know.” Wilson also performed “4X4XU,” co-written with Kentucky-born songwriters Aaron Raitiere and Jon Decious, which resonated deeply with the local crowd.

A highlight was her performance of “Somewhere Over Laredo,” a recent release that garnered over 1.16 million streams in its first 24 hours. Wilson’s ability to connect with the audience was wonderful—she worked the crowd like a seasoned performer, sharing stories of her journey and hyping up the Kentucky faithful. Her set was a perfect blend of heartfelt ballads and high-energy anthems, leaving the crowd buzzing with excitement.

Jelly Roll’s Emotional Sunday Finale Jelly Roll, sporting a 200 lb. leaner frame, closed out the festival on Sunday night with a performance that was both soulful and triumphant and high energy. The Nashville artist, whose real name is Jason DeFord, brought his unique blend of country, hip-hop, and rock to the Limestone Stage, delivering a set that was as emotionally raw as it was celebratory. Songs like “Son of a Sinner” and “Need a Favor” had the crowd singing along, their voices echoing across the infield.

Jelly Roll’s authenticity shone through as he shared stories of his personal struggles and redemption, connecting with fans on a profound level. A particularly moving moment came when he dedicated a song to a fan in the crowd who had held up a sign sharing their own story of overcoming cancer. This impromptu interaction turned the performance into a communal experience, with the audience visibly moved. Jelly Roll’s set was a testament to his ability to bridge genres and emotions, making it a fitting capstone to the weekend. He probably had more fun than the audience.

Standout Daytime Performances While the headliners were undeniably stellar, the daytime acts on all three stages were the heart of Railbird 2025. The Red Clay Strays, a Southern rockabilly band, delivered a Sunday set on the Limestone Stage that was described by many as a festival highlight. Their infectious energy and danceable tunes, like “Wondering Why,” had the crowd swaying and singing along. Twenty four year old Wyatt Flores, a rising star in the Americana scene, brought raw emotion to his Saturday performance on the Limestone Stage, with songs like “Please Don’t Go” resonating with fans who appreciate his introspective songwriting. Sierra Ferrell (born August 3, 1988), another standout, enchanted the audience with her ethereal voice and folk-infused set, performing tracks like “Fox Hunt.” Shaboozey’s Saturday evening set was a breakout moment, with his chart-topping “A Bar Song (Tipsy)” igniting the crowd and proving his staying power beyond a single hit.

Other notable performances included Cody Jinks’ gritty outlaw country set on the Elkhorn Stage, and Luke Grimes’ soulful performance on the Burl Stage, which drew fans of his Yellowstone fame. Smaller acts like Ruston Kelly (former husband of Kacey Musgraves), The Castellows, and Maggie Antone also left their mark, showcasing the festival’s commitment to spotlighting both established and emerging talent. The third artist from the Yellowstone series was Ryan Bingham, who had lost a few pounds and has grown a cowboy moustache. More on that, HERE.

The Massive Crowd and Their Reactions

The crowd at Railbird 2025 was slightly smaller than the previous year’s peak of nearly 45,000 daily attendees, but the energy was no less electric. The festival’s pivot to a more pop-country lineup with headliners like Lainey Wilson and Jelly Roll attracted a diverse audience, ranging from young fans in cowboy hats to older attendees drawn to the Americana and folk acts. The atmosphere was festive yet relaxed, with a strong sense of community permeating the infield. Fans were particularly vocal about their love for the daytime acts, with social media posts buzzing about The Red Clay Strays and Sierra Ferrell as unexpected highlights. Wait times at the entrance were longest between 2 and 5 p.m. each day, but those who arrived early or later reported a smoother experience. The crowd’s enthusiasm was electric during Jelly Roll’s emotional set, with many fans visibly moved by his candid storytelling. Despite the occasional muddy patches from rain, attendees embraced the Kentucky spirit, dancing and singing through the drizzle.

Vendors: A Taste of Kentucky

Railbird’s vendor offerings were a highlight, showcasing Kentucky’s culinary and cultural heritage. The Bourbon Hideout, curated by Justin Sloan and Justin Thompson of Justins’ House of Bourbon, offered hand-selected barrels from Kentucky’s finest distilleries, drawing bourbon enthusiasts eager to sample rare pours. Food vendors served up local favorites, from barbecue to craft beer, though some attendees noted high prices typical of festival settings. A new addition in 2025 was a large tent featuring vintage vendors and local artisans, offering unique crafts and festival merchandise. The vendor layout was functional, with minimal wait times for food and drinks, though bathroom lines could get lengthy during peak hours. The combination of music, bourbon, and local eats created a distinctly Kentucky experience that complemented the festival’s musical offerings.

Final Thoughts

Railbird Festival 2025 was a great festival, well run, and blending a world-class music lineup with the soul of Kentucky. Lainey Wilson and Jelly Roll delivered headlining sets that lived up to the hype, while daytime acts like The Red Clay Strays, Wyatt Flores, and Sierra Ferrell proved the festival’s strength lies in its diverse lineup. The massive crowd brought infectious energy, undeterred by threat of rain and muddy conditions. Vendors added a local flavor, with bourbon – lots and lots of bourbon– and food options that celebrated the region’s heritage. Despite a slight shift toward pop-country, Railbird retained its Americana roots, creating a weekend that felt both intimate and grand. For music lovers, bourbon aficionados, and anyone seeking a taste of Kentucky’s vibrant culture, Railbird 2025 was a weekend to remember.

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