Bluegrass Brunch at The Ruffed Grouse Tavern
2026-05-24 10:00 - 10:30, 2026-05-31 10:00 - 10:30 (America/New_York) | Highlander Mountain House, 270 Main St, Highlands, NC, 28741, United States
Join us at The Ruffed Grouse Tavern at Highlander Mountain House as we host Bluegrass Brunch– every Sunday with music from 10:30 a.m. – 1 p.m.

Live Music with Katie and Ezra at The Vineyard at High Holly
2026-05-24 14:00 - 17:00 | The Vineyard at High Holly, 37 High Holly Rd, Scaly Mountain, NC, 28775, United States
Join us and enjoy an afternoon with great wine and live music with Katie and Ezra at The Vineyard at High Holly!

Live Music with Adam & Joe at The Vineyard at High Holly
2026-05-25 14:00 - 17:00 | The Vineyard at High Holly, 37 High Holly Rd, Scaly Mountain, NC, 28775, United States
Join us and enjoy an afternoon with great wine and live music with Adam & Joe at The Vineyard at High Holly!

Live Music at Cashiers Celtic Table
2026-05-27 17:00 - 21:00, 2026-06-03 17:00 - 21:00 | Cashiers Celtic Table, 341 U.S. 64, Cashiers, NC, 28717, United States
Join us at Celtic Table for Live Music Wednesdays!

Bluegrass Wednesday at The Ugly Dog Pub
2026-05-27 18:30 - 21:00, 2026-06-03 18:30 - 21:00 | The Ugly Dog Pub – Highlands, 294 S 4th St, Highlands, NC, 28741, United States
Bluegrass Wednesday with Nitrograss is back at The Ugly Dog!
Come enjoy dinner and your favorite bluegrass band!

Blues Night at Ruffed Grouse Tavern at Highlander Mountain House
2026-05-28 18:00 - 20:00, 2026-06-04 18:00 - 20:00 | Highlander Mountain House, 270 Main St, Highlands, NC, 28741, United States
Join us for Blues Night with Scott Low every Thursday night at the Ruffed Grouse Tavern.

Carolina Concert Series at Trailborn Highlands
2026-05-28 18:00 - 21:00, 2026-06-04 18:00 - 21:00 | Trailborn Highlands, 96 Log Cabin Ln, Highlands, NC, 28741, United States
Join us in the Trailborn Highlands backyard for live music and drinks during our Carolina Concert Series!

Live Music with Lucas Smith at The Vineyard at High Holly
2026-05-29 15:00 - 18:00 | The Vineyard at High Holly, 37 High Holly Rd, Scaly Mountain, NC, 28775, United States
Join us and enjoy an afternoon with great wine and live music with Lucas Smith at The Vineyard at High Holly!

Live Music at Hummingbird Lounge
2026-05-29 17:30 - 22:00, 2026-05-30 17:30 - 22:00, 2026-06-05 17:30 - 22:00 | Old Edwards Inn and Spa, 445 Main Street, Highlands, NC, 28741, United States
Plush easy chairs, sofas, and antique bistro tables invite you to sit back and embrace the carefree ambiance surrounding you. Live entertainment every Friday and Saturday night with Cy Timmons.

Bear Shadow Music Festival
2026-05-29 18:00 | NC
Welcome to Bear Shadow, a 3-day music festival in Highlands, North Carolina!
We’re proud to announce our 5th year of incredible live music with beautiful mountain scenery, warm spring temperatures, and unique flora and fauna. We’re also excited to introduce you to new experiences, fan-favorite daytime events, and as always, incredible Grammy-worthy live performances.
Join us for Friday’s benefit concert supporting Stage4Hope featuring Colton Bowlin and headliner, The Infamous Stringdusters!

Friday Night Live Concert Series | Andrew Wakefield & Friends at Town Square
2026-05-29 18:00 - 20:30 | Town Square, Main Street, Highlands, NC, 28741, United States
Friday Night Live | Showcasing Traditional Mountain Music and Local Talent
Andrew Wakefield & Friends
With a knack for song-craft and a boundless passion for the guitar, Chimney Rock-based Andrew Wakefield has become a western North Carolina bluegrass fixture while word of his talent continues to spread further. Weaving old with new, blurring genres, and pouring heart and soul into every live performance, Andrew brings the bluegrass scene something always needed: a sound and style of his own. Career highlights include performing with Molly Tuttle, members of Old Crow Medicine Show, Billy Strings, Sierra Ferrell, Fireside Collective, Songs From the Road Band, Jon Stickley Trio, Larry Keel’s Natural Bridge, and Larry Stephenson Band.

Groovin’ on the Green | Live Music with Dylan Armour at The Village Green
2026-05-29 18:00 - 20:30 | The Village Green, 160 Frank Allen Road, Cashiers, NC, 28717, United States
Join us for Groovin’ on The Green featuring Dylan Armour!
Groovin’ on The Green is FREE and takes place rain or shine on the Commons Lawn at The Village Green. Food and beverage vendors will be available at each concert and concert-goers are welcome to bring their own picnics and coolers. Please bring your own lawn chairs and blankets; personal tents are not allowed at Groovin’.

Live Music at Happs Place
2026-05-29 18:00 - 21:00 | Happs Place, 5914 NC-107, Glenville, NC, 28736, United States
Live music with Blue Jazz is in full swing at Happ’s Place, where great food, mountain vibes, and local talent come together all season long.

Live Music on the Patio at The Ruffed Grouse Tavern
2026-05-30 13:00 - 15:00, 2026-06-06 13:00 - 15:00 | Highlander Mountain House, 270 Main St, Highlands, NC, 28741, United States
Join us for live music on the patio every Saturday at The Ruffed Grouse Tavern at the Highlander Mountain House!

Bear Shadow Music Festival
2026-05-30 15:30 | Bear Shadow Base Camp, Highlands, NC, 28741, United States
Welcome to Bear Shadow, a 3-day music festival in Highlands, North Carolina.
We’re proud to announce our 5th year of incredible live music with beautiful mountain scenery, warm spring temperatures, and unique flora and fauna. We’re also excited to introduce you to new experiences, fan-favorite daytime events, and as always, incredible Grammy-worthy live performances.
Join us on Saturday for a wonderful day filled with amazing performances from J & The Causeways, Marc Broussard, Mavis Staples and Trombone Shorty!

Saturdays on Pine Concert Series | SNAP at Kelsey Hutchinson Founders Park
2026-05-30 18:00 - 20:30 | Kelsey-Hutchinson Founders Park, 411 Pine St., Highlands, NC, 28741, United States
Saturdays on Pine | Featuring a variety of popular regional bands and musicians
SNAP
Snap is a compact, high-energy quartet delivering rocking funk and phunky pop perfection. From soulful R&B and explosive pop-punk to hip-hop and classic rock, they’re masters of mashups and medleys. With over 20 years of professional experience, Snap brings stellar performances, reliability, and nonstop fun to every event, guaranteed to energize any crowd.

Live Music at Happs Place
2026-05-30 18:00 - 21:00 | Happs Place, 5914 NC-107, Glenville, NC, 28736, United States
Live music with James Gang is in full swing at Happs Place, where great food, mountain vibes, and local talent come together all season long.

The Texas Tenors ENCORE at Highlands PAC
2026-05-30 19:30 | Highlands PAC, 507 Chestnut Street, Highlands, NC, 28741, United States
ENCORE: Back by Popular Demand: The Texas Tenors are the most successful music group and third highest selling artist in the history of America’s Got Talent!
Since appearing on the series in 2009, JC, Marcus and John have performed over 2000 concerts, recorded 5 studio albums, produced 2 PBS Specials, and have written two hit children’s books earning them impressive recognition including 3 Emmy Awards, The Gelett Burgess Award for Excellence in Children’s Literature and the distinction of being Billboard Magazine’s #10 Classical Artist in the World. The tenors’ most recent albums “Outside the Lines”, “Rise” and “A Collection of Broadway and American Classics” all debuted at #1 on the Billboard Charts.

Bear Shadow After Party With Jeremy Ivey at Highlander Mountain House
2026-05-30 21:30 | Highlander Mountain House, 270 Main St, Highlands, NC, 28741, United States
Live music happens in our Ruffed Grouse Tavern at the Highlander Mountain House Hotel.
Spend your post-festival night cap in our cozy mountain with brilliant songwriter, Jeremy Ivey!
Parking available on the property or street behind HMH. Seating for the show is first come first serve.

Bear Shadow Music Festival
2026-05-31 12:30 | Bear Shadow Base Camp, Highlands, NC, 28741, United States
Welcome to Bear Shadow, a 3-day music festival in Highlands, North Carolina.
We’re proud to announce our 5th year of incredible live music with beautiful mountain scenery, warm spring temperatures, and unique flora and fauna. We’re also excited to introduce you to new experiences, fan-favorite daytime events, and as always, incredible Grammy-worthy live performances.
Join us on Sunday for a wonderful day filled with amazing performances from Pony Bradshaw, Kashus Culpepper, Margo Price and Charley Crockett!

Live Music with Jordan Denton at The Vineyard at High Holly
2026-05-31 14:00 - 17:00 | The Vineyard at High Holly, 37 High Holly Rd, Scaly Mountain, NC, 28775, United States
Join us and enjoy an afternoon with great wine and live music with Jordan Denton at The Vineyard at High Holly!

Live Music at Happs Place
2026-06-05 18:00 - 21:00 | Happs Place, 5914 NC-107, Glenville, NC, 28736, United States
Live music with Zac Kellum is in full swing at Happs Place, where great food, mountain vibes, and local talent come together all season long.
