Trailside Music Hall
Events at this venue
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Free Whiskey Band: Tribute to the Pogues and the Music of Shane McGowan
Trailside Music Hall 155 Kent St, Charlottetown, PE, CanadaThe Free Whiskey Band will play a matinee tribute show to the Pogues and the music of Shane McGowan at Trailside on March 7 at 12 noon. Celebrate the energizing music of The Pogues and Shane MacGowan with the “New” Free Whiskey Band, featuring Davy Weale, Peter Webb, Kat MacNeil, Thomas Kirkham, David Pendergast, Peter…
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Music PEI: Music Mosaic Rainbow Edition
Trailside Music Hall 155 Kent St, Charlottetown, PE, CanadaMusic PEI Week 2026 runs from February 28–March 7. The longstanding community festival marks a significant milestone this year: its 25th anniversary. Music PEI Week 2026 reflects both its past and future with new events, unexpected venues, and collaborations, combined with nostalgia sprinkled throughout the festival. Music Mosaic, presented by Pride PEI, takes place at…
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Ben Caplan and special guest Zebedee
Trailside Music Hall 155 Kent St, Charlottetown, PE, CanadaBen Caplan will perform with special guest Zebedee at Trailside on March 5 at 8 pm. Halifax’s Ben Caplan is a singer, songwriter, and live performer known for his unmistakable baritone voice and emotionally immersive concerts. Blending folk, blues, gospel, and Eastern European influences, his music often feels less like a performance and more like…
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Tara MacLean with KINLEY and Ben Aitken
Trailside Music Hall 155 Kent St, Charlottetown, PE, CanadaTara MacLean will perform with KINLEY and Ben Aitken at Trailside on March 1 at 8 pm. Tara MacLean is an internationally renowned, multi-award-winning singer-songwriter, best-selling author, and playwright from Epekwitk/PEI. Over a 30-year career, she has made seven solo albums and two with her JUNO Award-nominated band Shaye. She has toured with Dido, the…
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The Soosh
Trailside Music Hall 155 Kent St, Charlottetown, PE, CanadaThe Soosh plays at Trailside on February 28 at 8 pm.
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Boots and Bets: A Night of Country Fun and Casino Action in support of the PEI Symphony Orchestra
Trailside Music Hall 155 Kent St, Charlottetown, PE, CanadaDust off your boots, dress in western gear, try your luck at the tables, take a spin on the dance floor, and browse silent auction items—all in support of the PEI Symphony Orchestra. Tickets include $1000 in casino cash.
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Brothers MacPhee Nirvana Unplugged in NY
Trailside Music Hall 155 Kent St, Charlottetown, PE, CanadaJoin Curtis, Alex, Cory, Laurie, Dave, and Kev for a night of Nirvana Unplugged in New York, performing their rendition of the full-length album front to back. Unplugged was released on November 1, 1994. Audience members can sing along to all their favourites from this nostalgic album. After the album is finished, there will be…
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A Night of Songs & Stories with Shane Pendergast, Emilea May, and Liam Corcoran
Trailside Music Hall 155 Kent St, Charlottetown, PE, CanadaShane Pendergast has folk music in his blood. Hailing from a long lineage of storytellers and musicians in PEI, he is keeping the Maritime folk tradition alive with his honest and insightful compositions. From acclaimed folk festivals around the world to the small halls of PEI, Shane has cemented himself as one of Atlantic Canada’s…
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After Hours Band
Trailside Music Hall 155 Kent St, Charlottetown, PE, CanadaThis powerhouse six-member PEI cover band—featuring seasoned pros from Haywire and Ninth Hour—brings together Kenny Vail, David Rashed, Dean MacKinnon, Ron Atkinson, Matt Anderson, and Will MacKinnon for an electrifying live experience. With a guitar- and keyboard-driven sound, they deliver a high-energy mix of 80s and 90s rock and pop hits from Van Halen, Journey,…
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After Hours Band
Trailside Music Hall 155 Kent St, Charlottetown, PE, CanadaThis powerhouse six-member PEI cover band—featuring seasoned pros from Haywire and Ninth Hour—brings together Kenny Vail, David Rashed, Dean MacKinnon, Ron Atkinson, Matt Anderson, and Will MacKinnon for an electrifying live experience. With a guitar- and keyboard-driven sound, they deliver a high-energy mix of 80s and 90s rock and pop hits from Van Halen, Journey,…
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Valentine’s Sunday Brunch ft. Lawrence Maxwell and Kelley Mooney & Route 225
Trailside Music Hall 155 Kent St, Charlottetown, PE, CanadaA Valentine's Sunday Brunch featuring Lawrence Maxwell and Kelley Mooney & Route 225 takes place at Trailside on February 15 at 1 pm.
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Amanda Jackson and Route 225 Valentine’s Show
Trailside Music Hall 155 Kent St, Charlottetown, PE, CanadaAfter a debut sold-out show, Amanda Jackson and Route 225 return with a special Valentine’s show.
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Dee Hernandez: Ella Fitzgerald Tribute
Trailside Music Hall 155 Kent St, Charlottetown, PE, CanadaDee Hernandez will give a tribute to Ella Fitzgerald at Trailside on February 13 at 8 pm.
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Quittin’ Time: Zach Bryan Tribute
Trailside Music Hall 155 Kent St, Charlottetown, PE, CanadaQuittin' Time, the Zach Bryan Tribute band, plays at Trailside on February 7 at 8 pm.
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The Trio From Mars Album Launch with Wrong Planet Band
Trailside Music Hall 155 Kent St, Charlottetown, PE, CanadaThe Trio From Mars will launch their new Music PEI-nominated album General Store with Wrong Planet Band at Trailside on February 6 at 8 pm.
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Glory Days: The Music of Bruce Springsteen
Trailside Music Hall 155 Kent St, Charlottetown, PE, CanadaPresented by Craig Fair Productions, Glory Days: The Music of Bruce Springsteen plays at Trailside on January 29–31 at 8 pm.
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Glory Days: The Music of Bruce Springsteen
Trailside Music Hall 155 Kent St, Charlottetown, PE, CanadaPresented by Craig Fair Productions, Glory Days: The Music of Bruce Springsteen plays at Trailside on January 29–31 at 8 pm.
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Glory Days: The Music of Bruce Springsteen
Trailside Music Hall 155 Kent St, Charlottetown, PE, CanadaPresented by Craig Fair Productions, Glory Days: The Music of Bruce Springsteen plays at Trailside on January 29–31 at 8 pm.
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Lady Soul
Trailside Music Hall 155 Kent St, Charlottetown, PE, CanadaLady Soul will perform at Trailside on January 23 at 8 pm. Channeling soul and funk divas of yesterday and today, this nine-piece ensemble performs dynamic renditions of classic tracks by Aretha Franklin, Jackson 5, Christina Aguilera, Beyoncé, Bruno Mars, and more. Featuring Kelley Mooney, Emi Smith, and Heather McIsaac on vocals, the group includes…
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Brooke & Brad Play Country Classics
Trailside Music Hall 155 Kent St, Charlottetown, PE, CanadaBrooke MacArthur & Brad Milligan will perform at Trailside on January 17 at 8 pm. Between heartfelt ballads, boot scootin’ anthems, and playful duets, Brooke MacArthur & Brad Milligan pay homage to the nostalgic sounds of country classics from the 1990s–2000s.

![Pogues Tribute BLURRED [submitted]](https://buzzpeicom.twic.pics/2025/10/Pogues-Tribute-BLURRED-submitted-scaled.jpg)

![Ben Caplan press [Eduardo de la Cerda]](https://buzzpeicom.twic.pics/2025/10/Ben-Caplan-press-Eduardo-de-la-Cerda-scaled.png)
![Tara MacLean red [Jen Squires]](https://buzzpeicom.twic.pics/2025/10/Tara-MacLean-red-Jen-Squires.webp)
![mic joshua-hanson-Qizcmx0djrw-unsplash Photo by Joshua Hanson [Unsplash.com]](https://buzzpeicom.twic.pics/2023/10/mic-joshua-hanson-Qizcmx0djrw-unsplash-scaled.jpg)

![rock music guitar andre-mosele-b6H12dhARzk-unsplash Photo by Andre Mosele [Unsplash.com]](https://buzzpeicom.twic.pics/2023/06/rock-music-guitar-andre-mosele-b6H12dhARzk-unsplash-scaled.jpg)

![mic alfonso-scarpa-3adOGP7_RqA-unsplash Photo by Alfonso Scarpa [Unsplash.com]](https://buzzpeicom.twic.pics/2023/07/alfonso-scarpa-3adOGP7_RqA-unsplash-scaled.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)
![Route 225 with Amanda Jackson [submitted]](https://buzzpeicom.twic.pics/2025/10/Route-225-with-Amanda-Jackson-submitted.jpg)
![mic israel-palacio-Y20JJ_ddy9M-unsplash Photo by Israel Palacio [Unsplash.com]](https://buzzpeicom.twic.pics/2024/01/mic-israel-palacio-Y20JJ_ddy9M-unsplash-scaled.jpg)


![concert theatre stage music nick-moore-5zWN8DTNeVA-unsplash Photo by Nick Moore [Unsplash.com]](https://buzzpeicom.twic.pics/2025/02/concert-theatre-stage-music-nick-moore-5zWN8DTNeVA-unsplash-scaled.jpg)

![Brooke & Brad [submitted]](https://buzzpeicom.twic.pics/2025/10/Brooke-Brad-submitted.jpg)