MEET THE ARTISTS
Get to know the artists taking the stage at Ramblin’ Roads Country Fest 2026.
NICK BOSSE & THE NORTHERN ROOTS
HEADLINER
Nick Bosse is a New England-based singer-songwriter and Nashville recording artist known for his authentic, gritty take on country music. A lifelong musician, Nick began playing local cover gigs in 2013 before forming his backing band, The Northern Roots, who have been performing and traveling with him ever since.
With more than 2 million streams on his single “What Happened To Country,” a New England Music Award for Best Vocalist, and headlining performances at Foxwoods and Mohegan Sun, Nick Bosse & The Northern Roots bring a modern edge to a sound rooted in classic country.
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JASON INGRISELLI & THE MILES NORTH
Jason Ingriselli & The Miles North bring their own brand of “New England Country Music” to the stage, combining the ’90s country Jason grew up on with a touch of punk-rock influence and plenty of energy.
The band has built a loyal following through live performances across New England, sharing bills with national acts including Eli Young Band, Chris Janson, Matt Stell and Gretchen Wilson. Their growing momentum earned them a 2024 New England Music Award nomination for Country Act of the Year. Their recent music includes “Wide Open,” released in 2025.
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SHAELY O’DOU
Shaely O’Dou is a 17-year-old singer-songwriter from Vermont with a powerful voice and a natural way of connecting with an audience. She performs regularly throughout New England, playing everything from the country songs she loves to music of her own.
In July 2026, Shaely released her debut single, “Worth the Risk,” marking an exciting step toward sharing more original music. She’s continuing to grow as an artist, take on new opportunities, and see where music takes her next.
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JORDAN GLADU BAND
Jordan Gladu is a Western Massachusetts singer-songwriter blending Americana storytelling with modern pop influences. His music explores growth, resilience, and the pursuit of purpose, delivered through heartfelt lyrics and memorable melodies.
A familiar performer throughout Western Massachusetts, Jordan brings that same personal approach to his live shows and original music. His 2025 self-titled EP includes the original song “FREE.”
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CHARLIE DIAMOND
Charlie Diamond has wrestled an alligator, fought a tornado, been everywhere twice, and is thoroughly convinced he was reincarnated into the wrong decade. After running away with the circus at 16 and spending several years as a rigger, Charlie began writing songs while hiking the Appalachian Trail.
Much of his music is inspired by the mountain where he grew up, along with the people, places, adventures and oddities he’s encountered along the way. His original music includes “Modern Man in a Modern World,” recorded in Nashville with producer Dean Miller.
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August First is a New England-based band creating their own unique take on stringed music through a mix of originals and covers. After getting their start celebrating the many musical incarnations of Jerry Garcia, the band forged a sound all their own—one they’ve coined “Blues-Grassicana.”
Front woman Nicole D’Amico’s powerful vocals, tenor guitar and cello join Rick Schiffman’s passionate guitar playing, Brian Young’s mandolin and harmonica, and Dave Herera’s upright bass to create August First’s distinctive sound. The band has performed throughout New England and New York and appeared at festivals ranging from Jerry Jam and StrangeCreek to Oregon’s nationally known Northwest String Summit.
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Instagram • Facebook • YouTube • Soundcloud
AUGUST FIRST
AMANDA MELI
Amanda Meli is a singer-songwriter who believes every song tells its own story. Rather than writing within a single genre, she “serves the song,” allowing each piece to become whatever it needs to be—whether rock, folk, blues, acoustic, or country.
For Ramblin’ Roads, Amanda celebrates the tradition of country songwriting with songs from artists who have inspired her, including Johnny Cash and Dolly Parton, alongside original country music of her own. Rooted in honesty and storytelling, her writing explores resilience, love, loss, staying true to yourself, and finding the courage to keep moving forward. Her original music includes her 2025 single, “I.”
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HUNTER MCKINNON
Hunter McKinnon is a musician based in Amesbury, Massachusetts, who has been playing guitar for eight years and recently began bringing his music to the stage. Though relatively new to live performing, his love for music has been years in the making.
For Hunter, performing is about more than playing songs—it’s about creating an atmosphere where people can relax, enjoy the moment, and step away from the day-to-day. He loves connecting with a crowd through music and watching people settle in, unwind, and enjoy the experience.
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DAVID KEITH
David Keith is a rising Americana artist out of central Massachusetts, blending country grit, folk storytelling, and rock energy into a sound that feels both timeless and fresh. Since stepping onto the scene in 2022, he’s built a reputation for delivering high-impact live shows—mixing crowd-favorite covers with original songs. David brings a raw, magnetic presence, his shows aren’t just performances—they’re experiences
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BRIE GREEN
Brie Green, raised on a small farm in a small town in Massachusetts, is everywhere and nowhere all at once. She’s a bird in flight, playing in several bands around New England with genres from folk to funk, bluegrass to blues, country, swing, and things in between. One of four sisters, she’s a singer-songwriter, bassist, guitarist, fiddler, and co-founder of the band The Green Sisters (“New England’s hilarious and beloved sibling folk group”), with two albums out in the world. Brie is also the front woman to her own band, BriezyJane & the Hurricane, and always churning up a storm of good musical fun. In 2024 Brie put out her first “solo” album, titled “On the Path You Walk”, before thru-hiking the Appalachian Trail - two glorious adventures (that she’d do again in an instant). The album features 14 original songs full of heart, depth, longing, love, and light, recorded with the support of many amazing musician friends and family members. She’s grateful to be here - there are hundreds more songs to share and many more miles to wander.
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Website • GreenSisters • Instagram • FacebookBriezyJane • FacebookBrieGreen • YouTube
THE RAY GIFFORD BAND
Ray Gifford is a performing songwriter who plays solo when not rockin with his power trio. The Ray Gifford Band is a country/classic rock band from Southern Vermont. They take great pride in their fun and engaging entertainment style, and professionalism.
Playing in the New England area for years, they have become a regional favorite. They perform originals written by Ray Gifford that span a few genres from Country, Blues, to Pop, and Americana.
They also enjoy playing timeless covers from your favorite Country and Classic Rock bands. Together, they have a combined experience of over 90 years.
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STAN MATTHEWS
In the span of 50 years, I’ve played blues, rock n roll, metal, punk, jazz and country. I’ve attended Berklee college of Music. Recipient of the 2021 International singer Songwriter’s Association Award. I’ve released 5 cd’s and 7 singles. I’m a 30 year soon to retire union truck driver. I live in North Brookfield with 5 kids, 11 chickens and a wife. “With the steady rhythm of an acoustic guitar and a warm, deep voice,reminiscent of traditional country music; Stan Matthews conjures up a vivid picture of the life of the working man. His joy, his struggles, and his losses. ”
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JAKE DOW
ERIC TROY
Eric Troy is an award-winning singer-songwriter from Massachusetts whose music blends classic Americana, country storytelling, and a distinctive vocal style. Largely self-taught and influenced by songwriters like John Prine, Eric has built his place in the regional music scene through live performances and songwriter showcases. His self-titled debut album, released in 2025, showcases his songwriting, guitar work, and roots-driven sound.
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