Trailside Music Hall

10/12/2026

Jake Vaadeland & The Sturgeon River Boys live at the Trailside in Charlottetown November 4th!!!

Tickets and more show info available at www.trailside.ca or Back Alley Music.

https://locarius.io/events/4908/jake-vaadeland-the-sturgeon-river-boys-november-4th-25-advance-30-day-of-show-doors-630-pm

22-year-old Jake Vaadeland from Cut Knife, Saskatchewan, has had an impressive year. He earned his first JUNO Award win, his first Canadian Country Music Award win and made history as the youngest artist to achieve ‘Road Gold’ Certification by selling 25,000 tickets in 12 months across Canada. P...

10/12/2026

The Charlottetown Jazz Ensemble live at the Trailside in Charlottetown November 1st!!! Doors 6:30 PM with Showtime 7 PM

Tickets and more show info available at www.trailside.ca or Back Alley Music.

https://locarius.io/events/5149/the-charlottetown-jazz-ensemble-november-1st-25-general-15-student-w-id-doors-630-pm-with-showtime-7-pm

Big Band music at The Trailside this Summer! The Charlottetown Jazz Ensemble performs Sunday, November 1st at The Trailside. Recent winner of the 2026 Music PEI Award for Jazz, the Charlottetown Jazz Ensemble is a true big band with full horn sections – 5 trumpets, 4 trombones and 5 saxes plus pia...

10/12/2026

Life in the Fast Lane: A Night of the Eagles live at the Trailside in Charlottetown October 29th, 30th & 31st!!!

Tickets and more show info available at www.trailside.ca or Back Alley Music.

https://locarius.io/events/3328/life-in-the-fast-lane-a-night-of-the-eagles-oct-29th-55-doors-630-pm (29th) /

https://locarius.io/events/3329/life-in-the-fast-lane-a-night-of-the-eagles-oct-30th-55-doors-630-pm (30th) /

https://locarius.io/events/3330/life-in-the-fast-lane-a-night-of-the-eagles-oct-31st-55-doors-630-pm (31st)

10/12/2026

Al Tuck live at the Trailside in Charlottetown October 28th!!!

Tickets and more show info available at www.trailside.ca or Back Alley Music.

https://locarius.io/events/5139/al-tuck-october-28th-25-doors-630-pm

Bring up Al Tuck’s name to any Canadian music insider, and you’d better find yourself a comfortable chair. Feist suspects that he might just be a living legend. Jason Collett called him the greatest songwriter of his generation. He is an awesome encyclopedia of popular music, a roving troubadour...

10/12/2026

Matt Minglewood Band - Final Show on PEI AND an early 80th Birthday Celebration! live at the Trailside in Charlottetown October 23rd & 24th!!! The 24th is SOLD OUT! Tickets are still available for 23rd!

Tickets and more show info available at www.trailside.ca or Back Alley Music.

https://locarius.io/events/4737/matt-minglewood-band-final-show-on-pei-and-an-early-80th-birthday-celebration-october-23rd-50-doors-630-pm

MATT MINGLEWOOD will be playing his two final shows on the island at the Trailside October 23rd and 24th to finish off an amazing career and run at the Trailside for the past 16 years since Meghann and I purchased it from Barb and Doug. This will also be an early 80th birthday celebration for Matt.....

10/12/2026

10/12/2026

Shane Pendergast Album Release live at the Trailside in Charlottetown October 22nd!!!

Tickets and more show info available at www.trailside.ca or Back Alley Music.

https://locarius.io/events/4797/shane-pendergast-album-release-show-october-22nd-30-doors-630-pm

Hailing from a long lineage of storytellers and musicians in Prince Edward Island, Shane Pendergast is keeping the Maritime folk tradition alive with his honest and insightful compositions. From acclaimed folk festivals across the world to the small halls of PEI, Shane has cemented himself as one of...

10/08/2026

TONIGHT! Huge show at the Trailside this Thursday, October 8th with Fu**ed Up and special guest opener Club Rat. Tickets on sale now at www.trailside.ca.