Trailside Music Hall
Events at this venue
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Got Blues Matinee
Trailside Music Hall 155 Kent St, Charlottetown, PE, CanadaGot Blues, led by Chris Roumbanis with friends Mike Robicheau and Alan Dowling, hosts a weekly Saturday matinee from 2–4 pm, now at Trailside Music Hall. Each week, a special guest joins the first set, followed by an electric blues jam in the second. There is no cover charge; they pass the hat. The upcoming…
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The Soosh
Trailside Music Hall 155 Kent St, Charlottetown, PE, CanadaThe Soosh performs at the Trailside Music Hall on June 12 at 8 pm. The Soosh is a retro funk band from PEI, blending the timeless sounds of Prince, Whitney Houston, Stevie Wonder, James Brown, and more into a fresh, electrifying live experience. From smoothed-out disco vibes to funky, bass-driven jams, The Soosh is here…
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Devin Cuddy
Trailside Music Hall 155 Kent St, Charlottetown, PE, CanadaDevin Cuddy performs at the Trailside Music Hall on June 11 at 8 pm. Devin Cuddy is a singer-songwriter based in Toronto. From an early age, he was drawn to music of the past. While sifting through his father’s (Jim Cuddy of Blue Rodeo) CD collection, he found the music of Louis Armstrong and New…
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blink-902
Trailside Music Hall 155 Kent St, Charlottetown, PE, Canadablink-902 kicks off the summer at the Trailside Music Hall on June 6 at 8 pm. Celebrating the 25th anniversary of Take Off Your Pants And Jacket, blink-902 will kick off the night by playing the 2001 pop-punk classic from front to back. After that, they've got a second set of other favourites from the…
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Got Blues Matinee
Trailside Music Hall 155 Kent St, Charlottetown, PE, CanadaGot Blues, led by Chris Roumbanis with friends Mike Robicheau and Alan Dowling, hosts a weekly Saturday matinee from 2–4 pm, now at Trailside Music Hall. Each week, a special guest joins the first set, followed by an electric blues jam in the second. There is no cover charge; they pass the hat. The upcoming…
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Lady Soul
Trailside Music Hall 155 Kent St, Charlottetown, PE, CanadaLady Soul performs at the Trailside on June 5 at 8 pm.
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Mama’s Broke
Trailside Music Hall 155 Kent St, Charlottetown, PE, CanadaMama’s Broke performs at the Trailside on June 3 at 8 pm.
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Ben Caplan
Trailside Music Hall 155 Kent St, Charlottetown, PE, CanadaBen Caplan at the Trailside on June 2 at 8 pm. With his deep, commanding baritone and electrifying stage presence, Caplan merges the raw energy of diverse folk traditions with modern innovation. His music isn’t just performed; it’s experienced. Now, with The Flood, Caplan takes his artistry to new depths, crafting an album that meditates…
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Charlottetown Jazz Ensemble
Trailside Music Hall 155 Kent St, Charlottetown, PE, CanadaRecipient of the 2026 Music PEI Achievement in Jazz Award, the band performs a mix of contemporary and classic big band charts, including standards by legends like Basie and Ellington, alongside contemporary swing, funk, Latin, and rock numbers. Doors open at 6 pm. Visit trailside.ca for tickets and follow @charlottetownjazz on FB for updates.
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Brother’s MacPhee: Nirvana Unplugged in New York
Trailside Music Hall 155 Kent St, Charlottetown, PE, CanadaCurtis, Adam, Cory, Laurie, Dave and Kev celebrate Nirvana’s MTV Unplugged in New York. They perform their rendition of the full-length album front to back. The album was released on November 1, 1994. Bonus Nirvana tracks, alongside a mash-up of ’90s grunge and alternative songs, round out the nostalgic evening.
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Got Blues Matinee
Trailside Music Hall 155 Kent St, Charlottetown, PE, CanadaGot Blues, led by Chris Roumbanis with friends Mike Robicheau and Alan Dowling, hosts a weekly Saturday matinee from 2–4 pm, now at Trailside Music Hall. Each week, a special guest joins the first set, followed by an electric blues jam in the second. There is no cover charge; they pass the hat. The upcoming…
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Garrett Mason
Trailside Music Hall 155 Kent St, Charlottetown, PE, CanadaGarrett Mason was raised in Truro, Nova Scotia, by his mother, Pam, and his father, veteran Canadian bluesman Dutch Mason. His path to becoming a blues musician began at an early age; surrounded by blues music, his favourite tapes at three were Canned Heat and Buddy Rich. Although his father stopped playing guitar before Garrett…
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Wild World: A Tribute to Cat Stevens/Yusuf
Trailside Music Hall 155 Kent St, Charlottetown, PE, CanadaThis tribute makes its debut with an evening dedicated to some of the most iconic songs of the 1970s. Performed by five accomplished musicians, the show celebrates the timeless music and remarkable journey of the artist known as Cat Stevens, later Yusuf, through a thoughtful blend of live performance and storytelling. The lineup features Mario…
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Amanda Jackson & Route 225
Trailside Music Hall 155 Kent St, Charlottetown, PE, CanadaAmanda Jackson and Route 225 return to Trailside on May 22 at 8 pm.
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The Jack Pine Folk Club
Trailside Music Hall 155 Kent St, Charlottetown, PE, CanadaThe Jack Pine Folk Club returns to Trailside Music Hall in Charlottetown on May 21. Doors open at 6:30 pm, with showtime at 7:30 pm. The Jack Pine Folk Club channels the spirit of a 1960s folk coffeehouse, as host Shane Pendergast leads an intimate evening of music, poetry, and revelry. Returning to the folk…
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Joce Reyome & Bobby Dove
Trailside Music Hall 155 Kent St, Charlottetown, PE, CanadaWinner of the 2025 Solo/Duo Category at the International Blues Challenge, Joce Reyome brings an authentic, engaging presence to the stage, turning audiences into active participants in a journey through heartbreak and humour. With performances at the Confederation Centre of the Arts Main Stage in Charlottetown, the Orpheum Theatre in Memphis, JUNOfest 2024, the East…
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Arthur Simeon: Funny African Guy
Trailside Music Hall 155 Kent St, Charlottetown, PE, CanadaUgandan-born Arthur Simeon brings his hilarious new stand-up comedy show, Funny African Guy, to Charlottetown’s Trailside Music Hall on May 17 at 8 pm. A favourite on CBC Radio’s The Debaters and a frequent guest on CTV’s The Social, Simeon is a gifted storyteller and delightful joke writer. He has toured all over the world…
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Got Blues Matinee
Trailside Music Hall 155 Kent St, Charlottetown, PE, CanadaGot Blues, led by Chris Roumbanis with friends Mike Robicheau and Alan Dowling, hosts a weekly Saturday matinee from 2–4 pm, now at Trailside Music Hall. Each week, a special guest joins the first set, followed by an electric blues jam in the second. There is no cover charge; they pass the hat. The upcoming…
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Matt Minglewood Band
Trailside Music Hall 155 Kent St, Charlottetown, PE, CanadaThe Matt Minglewood Band will perform at Trailside on May 15–16 at 8 pm.
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Matt Minglewood Band
Trailside Music Hall 155 Kent St, Charlottetown, PE, CanadaThe Matt Minglewood Band will perform at Trailside on May 15–16 at 8 pm.

![mic-robinson-recalde-sT0n-Ie8OKo-unsplash-scaled-1 Photo by Robinson Recalde [Unsplash.com]](https://buzzpeicom.twic.pics/2024/06/mic-robinson-recalde-sT0n-Ie8OKo-unsplash-scaled-1.jpg)

![Devin Cuddy [submitted]](https://buzzpeicom.twic.pics/2026/05/Devin-Cuddy-submitted.jpg)


![mic gift-habeshaw-PXuDwFcbcwY-unsplash Photo by Gift Habeshaw [Unsplash.com]](https://buzzpeicom.twic.pics/2024/02/mic-gift-habeshaw-PXuDwFcbcwY-unsplash-scaled.jpg)
![Ben Caplan press [Eduardo de la Cerda]](https://buzzpeicom.twic.pics/2025/10/Ben-Caplan-press-Eduardo-de-la-Cerda-scaled.png)




![mic joshua-hanson-Qizcmx0djrw-unsplash Photo by Joshua Hanson [Unsplash.com]](https://buzzpeicom.twic.pics/2023/10/mic-joshua-hanson-Qizcmx0djrw-unsplash-scaled.jpg)
![Route 225 with Amanda Jackson [submitted]](https://buzzpeicom.twic.pics/2025/10/Route-225-with-Amanda-Jackson-submitted.jpg)
![McMillans Camp Boys BW [submitted]](https://buzzpeicom.twic.pics/2026/01/McMillans-Camp-Boys-BW-submitted.webp)

![Arthur Simeon [submitted]](https://buzzpeicom.twic.pics/2026/04/Arthur-Simeon-submitted.jpg)
![Matt Minglewood guitar bw [submitted]](https://buzzpeicom.twic.pics/2024/09/Matt-Minglewood-guitar-bw-submitted-scaled.jpg)