Sunday, May 24, 2026

• Featured May 24, 2026 10:30 am Recurring

  Featured Bluegrass Brunch at The Ruffed Grouse Tavern


Featured May 24 @ 10:30 am Recurring

Bluegrass Brunch at The Ruffed Grouse Tavern

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.

• May 24, 2026 2:00 pm - 5:00 pm Recurring

  Live Music at The Vineyard at High Holly


May 24 @ 2:00 pm - 5:00 pm Recurring

Live Music at The Vineyard at High Holly

Join us for live music at The Vineyard at High Holly!

Monday, May 25, 2026

No events on this day.

Tuesday, May 26, 2026

No events on this day.

Wednesday, May 27, 2026

• Featured May 27, 2026 5:00 pm - 9:00 pm Recurring

  Featured Live Music at Cashiers Celtic Table


Featured May 27 @ 5:00 pm - 9:00 pm Recurring

Live Music at Cashiers Celtic Table

Join us at Celtic Table for Live Music Wednesdays!

• Featured May 27, 2026 6:00 pm - 9:00 pm Recurring

  Featured Bluegrass Wednesday at The Ugly Dog Pub


Featured May 27 @ 6:00 pm - 9:00 pm Recurring

Bluegrass Wednesday at The Ugly Dog Pub

Bluegrass Wednesday with Nitrograss is back at The Ugly Dog!

Thursday, May 28, 2026

• Featured May 28, 2026 6:00 pm - 8:00 pm Recurring

  Featured Blues Night at Ruffed Grouse Tavern at Highlander Mountain House


Featured May 28 @ 6:00 pm - 8:00 pm Recurring

Blues Night at Ruffed Grouse Tavern at Highlander Mountain House

Join us for Blues Night with Scott Low every Thursday night at the Ruffed Grouse Tavern.

• May 28, 2026 6:00 pm - 9:00 pm Recurring

  Carolina Concert Series at Trailborn Highlands


May 28 @ 6:00 pm - 9:00 pm Recurring

Carolina Concert Series at Trailborn Highlands

Join us in the Trailborn Highlands backyard for live music and drinks during our Carolina Concert Series!

Friday, May 29, 2026

• Featured May 29, 2026 5:30 pm - 10:00 pm Recurring

  Featured Live Music at Hummingbird Lounge


Featured May 29 @ 5:30 pm - 10:00 pm Recurring

Live Music at Hummingbird Lounge

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.

• Featured May 29, 2026 6:00 pm

  Featured Bear Shadow Music Festival


Featured May 29 @ 6:00 pm

Bear Shadow Music Festival

Join us for Friday's benefit concert supporting Stage4Hope featuring Colton Bowlin with headliner, The Infamous Stringdusters!

• Featured May 29, 2026 6:00 pm - 8:30 pm

  Featured Friday Night Live Concert Series | Andrew Wakefield & Friends at Town Square


Featured May 29 @ 6:00 pm - 8:30 pm

Friday Night Live Concert Series | Andrew Wakefield & Friends at Town Square

Join us in Town Square for Highlands’ Friday Night Live Concert Series featuring Andrew Wakefield & Friends!

• Featured May 29, 2026 6:00 pm - 8:30 pm

  Featured Groovin’ on the Green | Live Music with Dylan Armour at The Village Green


Featured May 29 @ 6:00 pm - 8:30 pm

Groovin’ on the Green | Live Music with Dylan Armour at The Village Green

Join us for Groovin’ on The Green featuring Dylan Armour!

• May 29, 2026 6:00 pm - 9:00 pm Recurring

  Live Music at Happs Place


May 29 @ 6:00 pm - 9:00 pm Recurring

Live Music at Happs Place

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.

Saturday, May 30, 2026

• May 30, 2026 1:00 pm - 3:00 pm Recurring

  Live Music on the Patio at The Ruffed Grouse Tavern


May 30 @ 1:00 pm - 3:00 pm Recurring

Live Music on the Patio at The Ruffed Grouse Tavern

Join us for live music on the patio every Saturday at The Ruffed Grouse Tavern at the Highlander Mountain House!

• May 30, 2026 2:00 pm - 5:00 pm Recurring

  Live Music at The Vineyard at High Holly


May 30 @ 2:00 pm - 5:00 pm Recurring

Live Music at The Vineyard at High Holly

Join us for live music at The Vineyard at High Holly!

• Featured May 30, 2026 3:30 pm

  Featured Bear Shadow Music Festival


Featured May 30 @ 3:30 pm

Bear Shadow Music Festival

Join us on Saturday for a wonderful day filled with amazing performances from J & The Causeways, Marc Broussard, Mavis Staples and Trombone Shorty!

• Featured May 30, 2026 5:30 pm - 10:00 pm Recurring

  Featured Live Music at Hummingbird Lounge


Featured May 30 @ 5:30 pm - 10:00 pm Recurring

Live Music at Hummingbird Lounge

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.

• Featured May 30, 2026 6:00 pm - 8:30 pm

  Featured Saturdays on Pine Concert Series | SNAP at Kelsey Hutchinson Founders Park


Featured May 30 @ 6:00 pm - 8:30 pm

Saturdays on Pine Concert Series | SNAP at Kelsey Hutchinson Founders Park

Join us in Kelsey Hutchinson Founders Park for Highlands’ Saturdays on Pine Concert Series featuring SNAP!

• May 30, 2026 6:00 pm - 9:00 pm Recurring

  Live Music at Happs Place


May 30 @ 6:00 pm - 9:00 pm Recurring

Live Music at Happs Place

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.

• Featured May 30, 2026 7:30 pm

  Featured The Texas Tenors ENCORE at Highlands PAC


Featured May 30 @ 7:30 pm

The Texas Tenors ENCORE at Highlands PAC

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!

• May 30, 2026 9:30 pm

  Bear Shadow After Party With Jeremy Ivey at Highlander Mountain House


May 30 @ 9:30 pm

Bear Shadow After Party With Jeremy Ivey at Highlander Mountain House

Spend your post-festival night cap in our cozy mountain with brilliant songwriter, Jeremy Ivey!