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DoRaleigh @[email protected] · 2026-05-18 · 18:04 UTC

Triangle Weekly Big Ticket Event Guide – Concerts, Comedy & Live Entertainment Across the Triangle

The Triangle is packed with major concerts, comedy shows, and live entertainment this week from May 18–25, 2026. From legendary artists like Sting, ZZ Top, and Pitbull to comedy favorites like J.B. Smoove and Funny Marco, there’s no shortage of big-ticket entertainment happening around Raleigh, Durham, Cary, Chapel Hill, Carrboro, and beyond.

Whether you’re looking for indie rock, country, reggae, comedy, orchestral performances, or tribute bands, this week’s lineup delivers something for every music and entertainment fan.

Monday, May 18, 2026

8:00 p.m. — ’68
Local 506
8:00 p.m. — Future Islands
Cat’s Cradle

Tuesday, May 19, 2026

7:30 p.m. — Clare Bowen & Jonathan Jackson
Goodnights Comedy Club
8:00 p.m. — Sting
Red Hat Amphitheater
8:00 p.m. — Josh Ritter
Haw River Ballroom
8:00 p.m. — Pitbull & Lil Jon
Coastal Credit Union Music Park at Walnut Creek
8:00 p.m. — Santigold
The Ritz
8:00 p.m. — Future Islands
Cat’s Cradle

Wednesday, May 20, 2026

7:00 p.m. — Distant
Local 506
8:00 p.m. — The New Pornographers
Haw River Ballroom
8:00 p.m. — Future Islands
Cat’s Cradle

Thursday, May 21, 2026

12:45 p.m. — Throwback Sounds of Summer
Rudy Theatre
7:00 p.m. — David Nail
Bird’s Nest Listening Room
7:30 p.m. — Chicago
Crown Theatre
7:30 p.m. — J.B. Smoove
Goodnights Comedy Club
8:00 p.m. — Robber Robber
The Pinhook
8:00 p.m. — Hiding Places
Cat’s Cradle – Back Room
8:00 p.m. — Dakota Proctor
The Pour House Music Hall

Friday, May 22, 2026

Friday’s lineup features some of the biggest shows of the week across the Triangle.

Iration & Tribal Seeds — Red Hat Amphitheater
ZZ Top & Dwight Yoakam — Koka Booth Amphitheatre
ATLiens — The Ritz
Funny Marco — Raleigh Improv
J.B. Smoove — Goodnights Comedy Club
The Secret Sisters — Fletcher Opera Theater
A Tribute to Dylan and Cash — The Wake Forest Listening Room at Magnolia Roots
Chris O’Connor — Room 861 at Goodnights
On The Border – The Eagles Tribute Band — Lincoln Theatre
Marisela — Raleigh Memorial Auditorium

Weekend Highlights: May 23–25

Saturday, May 23

Carrboro Bluegrass Festival — Cat’s Cradle – Back Yard
North Carolina Symphony: Sophie Mok – Tchaikovsky Piano Concerto No. 1 — Koka Booth Amphitheatre
Comedy performances from Funny Marco, J.B. Smoove, and Chris O’Connor continue throughout the evening.

Sunday, May 24

Jimmy Dore — Goodnights Comedy Club
Caleb Caudle — Cat’s Cradle
An American Celebration: The Music of John Williams — Koka Booth Amphitheatre
Sydney Castillo — Goodnights Comedy Club

Monday, May 25

8:00 p.m. — King Garbage
The Pinhook

Big Concerts & Comedy Shows Across the Triangle

This week’s Triangle Big Ticket Event Guide features some of the region’s biggest names in music, comedy, and live entertainment with events happening across Raleigh, Cary, Durham, Carrboro, Chapel Hill, Fayetteville, Wake Forest, and beyond.

For more concert announcements, nightlife coverage, comedy shows, and local entertainment news, visit DoRaleigh.

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