Trailside Music Hall

06/06/2026

July 2nd, 3rd & 4th

Craig Fair Productions Presents:
Big Love: The Music of Fleetwood Mac

Craig Fair Productions has been holding off on adding a gem like this to their catalogue. There is nothing quite like the music that Fleetwood Mac brought to the world and we are going to celebrate it exactly as it should be done. From the bluesy days to the folk rock days, this iconic band’s songs have touched the hearts of their audience. At Craig Fair Productions, they strive to bring that theatrical element to the stage and this will be just that. Fleetwood Mac’s music lends itself so well to n electrifying concert experience. Everything from The Chain, Big Love, Landslide, Don’t Stop, Go Your Own Way to some of their earlier recordings… they will hit it all. ✨

Don’t miss this one, get your tickets at the link in our bio
$55
Doors // 630pm
Showtime // 8pm

06/06/2026

Vintage 4.0: Ballads & Bangers Vol. II // June 30th

Act I: The Ballads, basically. It’s two sets. The first set is all the ballads and slower stuff - Tom Petty, Our Lady Peace, MR. Big, Collective Soul, Peter Gabriel - you get the idea. It’s the part where you actually sit and listen, have a drink and enjoy people who love these songs as much as you do. We arrange these songs with great care and we hope it shows.
Act II: The Bangers. In set two we just go for it. All the bangers. The Killers, U2, Fleetwood Mac, Mumford & Sons, Ed Sheeran, the list goes on. The songs everyone knows. The ones you’ve been singing in your car forever. That’s when it gets loud and fun. And honestly, the crowd kind of takes over at that point, which is the whole idea. It’s chaos in the best way. Vol. 1 was packed, and people had a really good time, so if you’re thinking about it, probably grab your tickets sooner rather than later.

Tickets on sale through link in bio
$30
Doors // 630pm
Showtime // 8pm

06/06/2026

Route 225 w/ Alyssa Harper // June 21st

Route 225 featuring Alyssa Harper and special guest Ben Aitken

Now recognized as PEI’s premier backup band, Route 225 has backed stand out artists including Amanda Jackson, Kelley Mooney, Lawrence Maxwell and more! Their reputation for professionalism and excellence has secured them three consecutive years supporting performers at the Cavendish Beach Music Festival plus a packed schedule of their own. With exceptional musicality and an expensive, genre-spanning repertoire, route 225 specializes in “ the best songs you may have forgotten.” from the soulful grooves of Little Feat to the electrifying energy of Tina Turner, they deliver unforgettable, crowd-pleasing performances every time they take the stage.

Get your tickets through the link in bio
$30
Doors // 630pm
Showtime // 8pm

06/06/2026

Route 225 w/ Craig Fair // June 20th

Route 225 featuring Craig Fair & special guest Ben Aitken

Now recognized as PEI’s premier backup band, Route 225 has backed stand out artists including Amanda Jackson, Kelley Mooney, Lawrence Maxwell and more! Their reputation for professionalism and excellence has secured them three consecutive years supporting performers at the Cavendish Beach Music Festival plus a packed schedule of their own. With exceptional musicality and an expensive, genre-spanning repertoire, route 225 specializes in “ the best songs you may have forgotten.” from the soulful grooves of Little Feat to the electrifying energy of Tina Turner, they deliver unforgettable, crowd-pleasing performances every time they take the stage.

Get your tickets through the link in bio
$35
Doors // 630pm
Showtime // 8pm

06/06/2026

Lil Godd // July 23rd

Viral sensation Lil Godd is bringing his explosive live show to Charlottetown PEI  this summer. Don’t miss this all-ages night packed with high-energy performances, viral hits, and unforgettable vibes.

Tickets on sale at www.diamondmineagency.ca // accessible through our website or link in bio

Doors // 630pm
Showtime // 8pm

06/06/2026

06/05/2026

Nathan Wiley w/ full band // September 18th

Summerside, PE’s Nathan Wiley first earned acclaim for his 2002 debut Bottom Dollar, which won the ECMA for Alternative Album of the Year and was chosen by Billboard Magazine as one of the top ten albums of 2002. His blend of classic sounds with a modern, slightly world weary perspective struck a chord with listeners as songs full of subtle melodies and lyrics addressing those unquenchable yearnings inside all of us worked their way into their ears. In the years that followed, Wiley has made good on the promise of Bottom Dollar with the ECMA-winning sophomore album High Low (2004), Steve Berlin (Los Lobos) produced Effort, The City Destroyed Me (2007), Bandits (2015) and most recently Modern Magic, which took home Music PEI’s Album of the Year and Songwriter of the Year as well as another ECMA nomination. Nathan recently scored the feature film Night Blooms and has shared the stage with artists like Blue Rodeo, Sarah Harmer, Steve Earle, Billy Bragg, Matt Mays, Ron Sexsmith and many more, while his work has appeared on TV, film and stage.

Tickets available through link in bio
$25
Doors // 630pm
Showtime // 8pm

06/05/2026

Luka Hall // August 22nd

Luka Hall is a dynamic singer-songwriter, guitarist and accomplished fiddle player from PEI, known for skillfully blending traditional fiddle and folk / country music. His 2024 EP ‘To Be Honest’ earned him significant recognition: 2025 Music PEI nominee (Traditional Roots Recording of the Year) and 2026 Canadian Folk Music award nominee (Young Performer of the Year). In November of 2025, Luka released an original Christmas song, ‘Maybe Next Christmas’ with Brooke MacArthur. A compelling live artist, Luka has captivated audiences at events including the PEI Festival of Small Halls Rollo Bay Fiddle Festival, Harmony House, Kings Playhouse, the 2026 Canadian Folk Music Awards and 2024 Your Roots Are Showing Folk Conference in Dundalk, Ireland. He is a promising young artist rapidly gaining traction in the Canadian music scene.

Tickets available through link in bio or at www.trailside.ca
$25
Doors // 630pm
Showtime // 8pm

06/02/2026

June 3 at the Trailside! Tickets on sale now at www.trailside.ca