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  • Dogs Do Magic ft. Magician Aaron Matthews

    Sobey Family Theatre 130 Queen St, Charlottetown, PE, Canada

    Magician Aaron Matthews will blend magic, comedy, and canines at the Sobey Family Theatre on May 23 at 2:30 pm.    

  • Lawrence Maxwell

    Bogside Brewing 11 Brook St, Montague, PE, Canada

    Live music at Bogside.

  • MadJoy

    Bogside Brewing Summerside 110 Water St, Summerside, PE, Canada

    Live music at Bogside Brewing in Summerside.

  • Music Bingo at The Factory

    The Factory 189 Kent St, Charlottetown, PE, Canada

    Music Bingo with Darcy Campbell on Saturdays at 7 pm.

  • Anne & Gilbert, The Musical

    Florence Simmons Performance Hall 140 Weymouth Street, Charlottetown, PE, Canada

    Anne & Gilbert, The Musical returns for its 22nd season this spring with a milestone debut: Island performer Holly Perry will take on the role of Anne Shirley for the…

  • Where’s Master Will?

    St Mark's Presbyterian 7 Tamarac Ave, Charlottetown, PE, Canada

    Where’s Master Will? will be presented at St. Mark’s Presbyterian in Charlottetown on May 21, 22, and 23 at 7 pm. This three-act comedy-mystery is written and directed by Barb…

  • Common Sound Concert Series

    Beaconsfield Historic/Carriage House 2 Kent St, Charlottetown, PE, Canada

    Common Sound launches on May 23 at 7 pm at Beaconsfield Carriage House in Charlottetown. The curated, year-round concert series presents one concert each month, featuring artists from across Atlantic…

  • May-hem with Side Hustle: Live Improv Comedy

    The Arts Guild 111 Queen St, Charlottetown, PE, Canada

    May-hem with Side Hustle will be on stage at The Arts Guild in Charlottetown on May 23 at 7:30 pm. May-hem is what happens when a group of quick-witted improvisers…

  • The Alan Jackson Experience

    Harbourfront Theatre 124 Heather Moyse Dr, Summerside, PE, Canada

    The Alan Jackson Experience comes to the Harbourfront Theatre on May 23 at 7:30 pm.    

  • Take the Mic Live Band Karaoke Season Finale

    19+
    The Old Triangle 189 Great George St, Charlottetown, PE, Canada

    Take The Mic brings the live band karaoke season finale to The Pourhouse in Charlottetown on May 23 at 7:30 pm. Backed by a live band, guests can sign up…

  • Dunk River Band

    Charlottetown Legion 99 Pownal St, CHarlottetown, PE, Canada

    Live music at the Charlottetown Legion. Everyone welcome.

  • Live DJ with DJ Jeremie

    19+
    Beer Garden Seafood Patio 190 Kent St, Charlottetown, PE, Canada

    Live DJ at Beer Garden. This is a 19+ event.

  • DJ Method

    19+
    The Factory 189 Kent St, Charlottetown, PE, Canada

    DJs on Fridays and Saturdays (11 pm) on the main floor.

  • The 2026 Book Awards

    Family Friendly
    Free event
    Charlottetown Library Learning Centre 97 Queen St, Charlottetown, PE, Canada

    The 2026 Book Awards will be held at the Charlottetown Library on May 24 at 10 am. The PEI Public Library Service and emcee Shawn Hogan will present the PEI…

  • Summerside Muckraker

    The 2026 Summerside Muckraker, the first mountain bike XC race of the season in Prince Edward Island and hosted by Cycling PEI, is scheduled for May 24 at Rotary Park…

  • Eptek Makers Session

    Free event
    Eptek Arts & Culture Centre 130 Heather Moyse Dr, Summerside, PE, Canada

    The next drop-in makers session at Eptek & Art Culture Centre is from 1–3 pm on May 24. Makers are invited to gather their latest project or one they have…

  • Sunday Session

    The Old Triangle 189 Great George St, Charlottetown, PE, Canada

    A Sunday Afternoon Tune Session featuring traditional music and craic takes place weekly on Sundays from 2–4 pm at The Old Triangle.

  • Nick Gauthier

    Slaymaker & Nichols 82 Fitzroy St, Charlottetown, PE, Canada

    Live music at Slaymaker & Nichols.