Darren Nicholson Band
I’ve always felt that there’s a particular sweetness to September on the Highlands-Cashiers Plateau.
The days still carry summer’s warmth, but by evening a coolness slips across the Plateau, inviting sweaters, easy conversation, and one more turn around the dance floor.
That’s when downtown comes alive with the Highlands Outdoor Concert Series, a free, family-friendly tradition that fills Friday and Saturday nights with music from 6:00 to 8:30 P.M. Presented by the Highlands Chamber of Commerce/Visit Highlands, NC, the series offers two distinct ways to enjoy the season’s final notes.
Friday Night Live gathers listeners in Town Square on Main Street, where bluegrass, country, Americana, and acoustic traditions feel right at home in the center of town.
Saturdays on Pine moves the celebration to Kelsey-Hutchinson Founders Park, where the lawn becomes a welcoming stage for beach music, funk, Motown, rock, country, and danceable favorites.
The September Friday Night Live lineup begins Friday, September 4, with Silly Ridge, a Highlands-based favorite known for lively bluegrass and familiar songs delivered with mountain ease.
On September 11, Byrds & Crows brings a thoughtful blend of folk, bluegrass, old country, Americana, and original music.
September 18 welcomes Blackwell Tradition II, carrying forward the North Georgia bluegrass legacy of Curtis Blackwell with heartfelt vocals and a traditional sound.
The Friday Night Live season closes September 25 with the Shortoff Mountain Boys, whose harmonies, old country influence, and local bluegrass spirit make them a natural fit for Town Square.
Saturday nights stretch the mood a little wider. Diverse Groove opens the month on September 5 with Top 40, beach music, Motown, R&B, rock, dance, and reggae. High 5 follows on September 12 with an easygoing mix of rock, blues, Americana, bluegrass, country, and jazz.
On September 19, Boogitherapi brings funk, smooth jazz, and groove‑heavy dance music to the park. Darren Nicholson Band closes the season on September 26 (5:00–7:30 P.M.) during the Highlands Heritage Jamboree with Western North Carolina bluegrass, folk, gospel, and swing.
Part of the pleasure is the simplicity. Bring a folding chair or picnic blanket, tuck a light jacket over your arm, and give yourself enough time to wander before the first notes begin. Town shops, casual restaurants, and early dinners all fit naturally into the rhythm of the evening. A wood-fired pizza, a pub bite, a little window shopping, or a refined meal can turn the concert into the centerpiece of a full Highlands night.
By September, the concerts feel less like an event and more like a farewell toast to the season: neighbors greeting neighbors, visitors discovering the easy grace of the Plateau, children moving to the beat, and music carrying into the trees.
Whether your favorite sound is a fiddle tune in Town Square or a groove in the park, the month offers four weekends of reasons to gather, listen, and linger under the Highlands sky.
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