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Trailside Music Hall

Address
155 Kent St
Charlottetown, PE C1A 1N5 Canada Get Directions
Phone 902-367-3311
Website https://trailside.ca

Events at this venue

Today

  • PEI’s Got Talent – Fundraiser for Blooming House

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

    Get loud for PEI’s Got Talent. Join Blooming House on April 29 at the Trailside Music Hall in Charlottetown for a high-energy night of music, dance, and other talent.  Local stars hit the stage and battle it out for cash prizes—expect big voices, bold moves, and crowd-favourite moments. Bring your friends, bring your cheers, and…

  • Photo by Robinson Recalde [Unsplash.com]

    Got Blues Matinee

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

    Got 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…

  • Kane Reinholdsten [Unsplash.com]

    Connor Fox

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

    A rising force in roots and blues rock, Connor Fox blends soulful guitar mastery with dynamic live performances. After gaining acclaim with The Hypochondriacs, he launched his debut solo album Music Room to sold-out shows and critical praise.

  • Photo by Magnus Lunay [Unsplash.com]

    Be Gay (or Not)—Donate to Pride

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

    Join Pride PEI for a vibrant variety show celebrating local talent while raising funds to support Pride Festival 2026. This fundraising event will bring together drag performers, musicians, comedians, dancers, and more for a night of entertainment, community, and Pride.

  • Charlottetown Jazz Ensemble

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

    The award-winning, 19-member Charlottetown Jazz Ensemble (CJE) will make its inaugural appearance at Trailside Music Hall in Charlottetown on April 12 at 7 pm. Recipient 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…

  • Photo by Magnus Lunay [Unsplash.com]

    Vintage 4.0

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

    Vintage 4.0 hits the stage at Trailside on April 10 at 8 pm. Vintage 4.0 has played a lot of rooms but this one is a little different. Ballads & Bangers is a two-set show with a purpose. The first set is built for a room that’s actually listening. Seated, drinks in hand, songs played…

  • PEI Comedians Showcase

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

    Celebrate the Island’s comedy scene at the PEI Comedians Showcase on April 9 at 8 pm at Trailside Music Hall in Charlottetown.  Hosted by local comedian Tanya Nicolle, the evening will showcase new and seasoned comics, including Liv Howlett, Nick Gaudet, Taylor Carver, Andrea Avery, Jesse Boutin, Jalen MacLeod, and Rachel Matheson.

  • Photo by Bogomil Mihaylov [Unsplash.com]

    Whose Line Is It Anyway? PEI Edition

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

    Comedian Jalen Macleod is bringing together a cast of local comedians to recreate the iconic and fan favourite show, “Whose Line is it Anyway?” The PEI edition will take place on April 4 at 8 pm at Trailside Music Hall in Charlottetown. Improv comedy with a local twist—what could go wrong? Sure to get audiences…

  • Photo by Robinson Recalde [Unsplash.com]

    Got Blues Matinee

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

    Got 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…

  • Riley Taylor

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

    Riley Taylor hits the stage at Trailside on April 3 at 8 pm. Raised in the small town of Burton, New Brunswick, and shaped by growing up in a military family, Riley’s music is rooted in real life, real places, and the stories that stay with the audience long after the night ends.

  • Joanie Pickens Band

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

    Joanie Pickens and her Band hits the stage at Trailside on April 2 at 8 pm. Sing along to hits by Trisha Yearwood, Martina Mcbride, Jo Dee Messina, Faith Hill, and more.

  • Photo by Michael Dobrinski [Unsplash.com]

    Girls Night Out: A Tribute to Canadian Female Rock Legends

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

    Girls Night Out: A Tribute to Canadian Female Rock Legends hits the stage at Trailside on March 28 at 8 pm. Music from Alanah Myles, Sass Jordan, Alanis, Toronto, Headpins, Lee Aaron and more will be featured.

  • Dave Gunning: Field Notes Album Release

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

    Dave Gunning will launch his new Field Notes album at Trailside on March 26 at 8 pm. With over two decades on the road and fifteen albums to his credit, Dave Gunning has earned a reputation as one of Canada’s most engaging and respected folk singer-songwriters. A multiple ECMA and CFMA Award winner, Gunning is…

  • Photo by Elijah Ekdahl [Unsplash.com]

    Dancing Queen: Tribute to ABBA

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

    Dancing Queen brings their tribute to ABBA to the Trailside on March 20–21 at 8 pm. Halifax’s Dancing Queen returns with their infectious stage show, getting audiences dancing and singing along to the ABBA hits they know and love: a selection of rarities and deep cuts, rounded out with some of the greatest disco songs…

  • Photo by Elijah Ekdahl [Unsplash.com]

    Dancing Queen: Tribute to ABBA

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

    Dancing Queen brings their tribute to ABBA to the Trailside on March 20–21 at 8 pm. Halifax’s Dancing Queen returns with their infectious stage show, getting audiences dancing and singing along to the ABBA hits they know and love: a selection of rarities and deep cuts, rounded out with some of the greatest disco songs…

  • The Fabulously Rich: Tragically Hip Tribute

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

    The Fabulously Rich pay homage and share their love for The Tragically Hip’s music. They look to keep the bands music alive and celebrate the magic that made The Tragically Hip. The Fabulously Rich began in 2016 with a fundraiser in Charlottetown after Gord Downie’s illness made headlines. Something special happened that night—people wanted more,…

  • The Fabulously Rich: Tragically Hip Tribute

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

    The Fabulously Rich pay homage and share their love for The Tragically Hip’s music. They look to keep the bands music alive and celebrate the magic that made The Tragically Hip. The Fabulously Rich began in 2016 with a fundraiser in Charlottetown after Gord Downie’s illness made headlines. Something special happened that night—people wanted more,…

  • Photo by Joshua Hanson [Unsplash.com]

    More Soul

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

    More Soul plays at Trailside on March 7 at 8 pm.

  • 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…