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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, Canada

    The 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…

  • Music PEI: Music Mosaic Rainbow Edition

    Trailside Music Hall 155 Kent St, Charlottetown, PE, Canada

    Music 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…

  • Ben Caplan and special guest Zebedee

    Trailside Music Hall 155 Kent St, Charlottetown, PE, Canada

    Ben 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…

  • Tara MacLean with KINLEY and Ben Aitken

    Trailside Music Hall 155 Kent St, Charlottetown, PE, Canada

    Tara 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…

  • The Soosh

    Trailside Music Hall 155 Kent St, Charlottetown, PE, Canada

    The Soosh plays at Trailside on February 28 at 8 pm.  

  • Brothers MacPhee Nirvana Unplugged in NY

    Trailside Music Hall 155 Kent St, Charlottetown, PE, Canada

    Join 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…

  • A Night of Songs & Stories with Shane Pendergast, Emilea May, and Liam Corcoran

    Trailside Music Hall 155 Kent St, Charlottetown, PE, Canada

    Shane 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…

  • After Hours Band

    Trailside Music Hall 155 Kent St, Charlottetown, PE, Canada

    This 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,…

  • After Hours Band

    Trailside Music Hall 155 Kent St, Charlottetown, PE, Canada

    This 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,…

  • Dee Hernandez: Ella Fitzgerald Tribute

    Trailside Music Hall 155 Kent St, Charlottetown, PE, Canada

    Dee Hernandez will give a tribute to Ella Fitzgerald at Trailside on February 13 at 8 pm.

  • Quittin’ Time: Zach Bryan Tribute

    Trailside Music Hall 155 Kent St, Charlottetown, PE, Canada

    Quittin' Time, the Zach Bryan Tribute band, plays at Trailside on February 7 at 8 pm.

  • Glory Days: The Music of Bruce Springsteen

    Trailside Music Hall 155 Kent St, Charlottetown, PE, Canada

    Presented by Craig Fair Productions, Glory Days: The Music of Bruce Springsteen plays at Trailside on January 29–31 at 8 pm.

  • Glory Days: The Music of Bruce Springsteen

    Trailside Music Hall 155 Kent St, Charlottetown, PE, Canada

    Presented by Craig Fair Productions, Glory Days: The Music of Bruce Springsteen plays at Trailside on January 29–31 at 8 pm.

  • Glory Days: The Music of Bruce Springsteen

    Trailside Music Hall 155 Kent St, Charlottetown, PE, Canada

    Presented by Craig Fair Productions, Glory Days: The Music of Bruce Springsteen plays at Trailside on January 29–31 at 8 pm.

  • Lady Soul

    Trailside Music Hall 155 Kent St, Charlottetown, PE, Canada

    Lady 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…

  • Brooke & Brad Play Country Classics

    Trailside Music Hall 155 Kent St, Charlottetown, PE, Canada

    Brooke 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.