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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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Town of Cary Weekly Event Guide May 18–24th Edition

Looking for things to do in Cary this week? From live music and public meetings to nature programs, historic preservation discussions, and major concerts, the Town of Cary has a full week of community events and entertainment planned from May 18 through May 24, 2026.

Whether you’re interested in local government, outdoor activities, arts and culture, or live performances, there’s something happening throughout Cary this week.

Monday, May 18, 2026

• Canceled: Planning and Zoning Board
  6:30 p.m.

Although this week’s Planning and Zoning Board meeting has been canceled, residents are encouraged to stay engaged with future development and growth discussions happening throughout Cary.

Tuesday, May 19, 2026

• Public Art Advisory Board
  6:15 p.m.

The Public Art Advisory Board meeting focuses on public art projects, cultural initiatives, and creative placemaking efforts throughout Cary.

Thursday, May 21, 2026

Nature is Nuts!

6:00 p.m.

Enjoy a fun and educational nature-focused program exploring trees, nuts, wildlife, and the environment. This family-friendly event is perfect for nature lovers and curious kids alike.

Greenway Committee

6:00 p.m.

The Greenway Committee discusses trails, greenway planning, outdoor recreation access, and future connectivity projects across Cary’s expanding park and greenway system.

Historic Preservation Series: The Changing Face of Downtown Cary

7:00 p.m.

Learn about the transformation and evolution of downtown Cary during this special historic preservation presentation focused on local history, redevelopment, architecture, and community growth.

Thursday Night Music Club: Rachel Sumner and Traveling Light

7:30 p.m.

Enjoy an evening of live music featuring Rachel Sumner and Traveling Light as part of Cary’s popular Thursday Night Music Club series.

Friday, May 22, 2026

ZZ Top & Dwight Yoakam: Dos Amigos Tour

Legendary rock band ZZ Top joins country music star Dwight Yoakam for the highly anticipated Dos Amigos Tour, bringing classic hits and live entertainment to the Triangle region.

Sunday, May 24, 2026

An American Celebration: The Music of John Williams

Celebrate the iconic film music of John Williams with a live orchestral performance featuring beloved scores from legendary movies and cinematic classics.

Explore More Things To Do in Cary This Week

From public art and greenway discussions to live music, nature programs, and major concerts, Cary continues to offer a strong mix of community engagement and entertainment opportunities throughout the week.

For more local event guides, Cary news, government updates, concerts, and things to do across the Triangle, visit DoRaleigh.

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