The Bear Shadow Music Festival bounds back into the Highlands scene May 29–31, promising three glorious days of music, mountains, and springtime revelry. What began as the Highlands Food & Wine Festival’s “wild little brother” has grown into its own creature, equal parts Southern swagger and mountain soul. This year’s festival unveils a new “Base Camp” at Ferngrove, Stacy Carter’s scenic property on Dillard Road, just three miles from downtown Highlands. With rolling pastures, tree-lined perimeters, and panoramic views, it’s an inspired new stage for Bear Shadow’s blend of live music, adventure, and community spirit. Expect favorites, from Summit & Sound hikes to live-stream fly-fishing, plus new surprises. As this article was being written, several of this year’s performers, Trombone Shorty, Margo Price, and Charley Crockett, were announced as Grammy nominees, underscoring Bear Shadow’s knack for curating artists whose star power matches their authenticity.
Saturday’s bill is anchored by New Orleans brass band royalty Trombone Shorty, the multi-instrumentalist who’s been electrifying audiences since he was four. Troy Andrews, who earned his nickname when he picked up a trombone bigger than himself, has spent a lifetime taking the sound of New Orleans to the world stage. His horn-driven fusion of funk, jazz, rock, and soul is pure kinetic energy. Sharing Saturday’s spotlight is Louisiana’s own Marc Broussard, the “Bayou Soul” ambassador whose smoky, gospel-tinged voice channels Otis Redding and Marvin Gaye. Broussard’s baritone and command of blues, rock, and funk have made him a festival favorite for two decades. Two additional Saturday acts will be announced soon, keeping anticipation high.
Sunday shifts the tempo but not the energy with a roots-rich lineup seemingly curated by the mountains themselves: Charley Crockett, Margo Price, Kashus Culpepper, and Pony Bradshaw. Crockett, the Texas troubadour with the vintage vinyl voice, evokes roadhouses and dusty highways, weaving blues, honky-tonk, and Western swing into something timeless. Price, one of Nashville’s most fearless singer-songwriters, brings fire and honesty to every lyric. Rising Alabama talent Culpepper adds Southern rock grit, while Bradshaw’s poetic Americana grounds the day in Appalachian storytelling.
The festival opens Friday with a VIP party and Stage4Hope fundraiser, setting the tone of purpose and community before the first note rings out. Bear Shadow has built a devoted following across the Southeast — fans who come not just for the music but for the camaraderie, the fresh air, and those hillside moments when the light softens, the bass kicks in, and the mountains seem to hum along. This spring, the bear awakens once more to remind us why there’s nothing quite like music under the Carolina sky.
Visit bearshadownc.com for details.
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