Live Music at Cashiers Celtic Table
2025-12-03 17:00 - 21:00, 2025-12-10 17:00 - 21:00, 2025-12-17 17:00 - 21:00 (America/New_York) | 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
2025-12-03 18:30 - 21:00, 2025-12-10 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
2025-12-04 18:00 - 20:00, 2025-12-11 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
2025-12-04 18:00 - 21:00, 2025-12-11 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 at The Vineyard at High Holly
2025-12-05 15:00 - 18:00, 2025-12-07 14:00 - 17:00, 2025-12-12 15:00 - 18:00, 2025-12-14 14:00 - 17:00 | The Vineyard at High Holly, 37 High Holly Rd, Scaly Mountain, NC, 28775, United States
Join us for live music at The Vineyard at High Holly!
Vineyard open hours 12-6 PM.

Appalachian Blues with Wooleybooger at Western Carolina Brew & Wine
2025-12-05 17:00 | Western Carolina Brew and Wine, 454 Carolina Way, Highlands, NC, 28741, United States
Join us at Western Carolina Brew & Wine!
Come grab a pint and enjoy Appalachian Blues with Wooleybooger!

Live Music at Hummingbird Lounge
2025-12-05 17:30 - 22:00, 2025-12-06 17:30 - 22:00, 2025-12-12 17:30 - 22:00, 2025-12-13 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.

Vino & Vibes | Live Music at High Country Wine and Provisions
2025-12-05 18:00 - 20:00 | High Country Wine & Provisions, 621 Franklin Rd, Highlands, NC, 28741, United States
Joins us for Vino & Vibes, live music every Friday at High Country Wine & Provisions!

Live Music at Happ's Place
2025-12-05 18:00 - 21:00, 2025-12-06 18:00 - 21:00, 2025-12-12 18:00 - 21:00, 2025-12-13 18:00 - 21:00 | Happs Place, 5914 NC-107, Glenville, NC, 28736, United States
Enjoy live music every Friday and Saturday at Happ’s Place in Glenville.

Live Music on the Patio at The Ruffed Grouse Tavern
2025-12-06 13:00 - 15:00, 2025-12-13 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!

Bluegrass Brunch at The Ruffed Grouse Tavern
2025-12-07 10:30, 2025-12-14 10:30 | 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.

Bear Shadow Music Festival TICKET DROP
2025-12-11 12:00 | NC
Tickets go on Sale Thursday, December 11 | 12pm https://bearshadownc.com/
Bear Shadow music festival made its debut in April 2021 at Winfield Farm in Scaly Mountain, just outside the city limits of Highlands, North Carolina.
A sister festival to the highly esteemed Highlands Food & Wine, Bear Shadow music festival is now a phenomenon all to itself, bringing celebrated artists to The Highlands-Cashiers Plateau for a weekend of music, mountains, and revelry each spring.

Live Music with Mick Mayer at Western Carolina Brew and Wine
2025-12-12 17:00 | Western Carolina Brew and Wine, 454 Carolina Way, Highlands, NC, 28741, United States
Join us at Western Carolina Brew & Wine!
Come grab a pint and enjoy live music from Mick Mayer!

Fireside at the Farm with Mike Kinnebrew at The Farm at Old Edwards
2025-12-17 18:00 - 20:00 | The Farm at Old Edwards, 336 Arnold Road, Highlands, NC, 28741, United States
Join us for the return of Fireside at The Farm: A Holiday Evening with Mike Kinnebrew.
Settle into the magical ambiance of The Farm on Wednesday, December 17, and relax into a special evening with the sounds of holiday music filling the pavilion. Mike’s talent for engaging the audience with music from the heart will make for an unforgettable evening.
Come experience this charming singer-songwriter and Highlands’ favorite for yourself.
