Union Winter Concerts and Events

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We are keeping the good times rolling all season long!

Tune in this winter for an exciting lineup of free music in the West Wing, located on street level, or bop to the beat at the Roller Express with a lineup of groovy DJ’s.
Explore our full programs below.

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West Wing Programming

Live performances in the West Wing

  • Hallelujah Chorus with Tafelmusik

    Dec 3 @ 5:00 PM–6:00 PM

    Hallelujah! Join Tafelmusik for a pop-up performance of the Hallelujah Chorus, from Handel’s Messiah, in Union’s West Wing. Bring your score and sing along or simply enjoy the music.

  • CBC Radio’s Here and Now presents Jordan Astra

    Dec 5 @ 5:00 PM–6:00 PM

    CBC Radio’s afternoon show, Here and Now, is pleased to present Jordan Astra live in as part of CBC Toronto’s holiday fundraising campaign, Make the Season Kind.

  • Royal Conservatory of Music

    Dec 9 @ 5:30PM—6:30 PM

    Join us for an evening of holiday music with performers from the Royal Conservatory of Music.

  • TD Music Celebrates the Holiday Season

    Dec 11 @ 4:00 PM–6:00 PM

    TD Music celebrates the Holiday Season with special musical performances by Kiesza and Shawnee Kish on Thursday, December 11 from 4pm to 6pm in the West Wing of Union Station. Both artists bring their pop and soulful sounds to the season with a mix of festive songs, their own holiday music, and fan-favourite hits.

  • Opera Express: Holiday Edition

    Dec 18 @ 5:30 PM–6:30 PM

    The Canadian Opera Company’s beloved partnership with Union Station returns for the annual holiday concert in the Opera Express series with COC Teaching Artists.

  • Belt Toronto

    Friday December 12th 5:30pm - 7pm

    Come sing with BELT Toronto and get in the Holiday Spirit.

    BELT is a musical theatre event company based in Toronto. We host both karaoke and choir-style nights that bring people together through singing and community. For this Union collaboration, we’ll be teaching a few holiday favourites in a fun caroling/choir-style environment.

Roller Express Programming

    • dj epik

      Dec 5

    • DJ Agile

      Dec 12

    • DJ Killa Kels

      Dec 19

    • DJ Fizza

      Jan 2

    • Starting from Scratch

      Jan 9

    • Dj Mensa

      Jan 16

    Union Beats Skate Nights

    Fridays @ 4:30 PM—8:30 PM

    Get your groove on and roll the night away on Friday nights from 4:30 PM—8:30 PM. Skate to the hottest DJ’s in the city

    • Starting from Scratch

      Dec 6

    • djnakz

      Dec 13

    • dassytoronto

      Dec 20

    • djmelboogie

      Dec 27

    • Starting from Scratch

      Jan 3

    • DJ Baby Yu

      Jan 10

    • DJ DVS

      Jan 17

    19+ Winter Mixers

    Saturdays @ 6:30 PM–11:00 PM

    Groove with us every Saturday for a fun night of beats and adult bevvies. And of course, free roller skating.

  • Free Skating Lessons

    Tuesdays, Thursdays, and Sundays

    Join us at Union Winter Roller Express for free roller skating lessons designed for all skill levels. To participate, register for the timeslot that the lesson falls within, and then sign up with the instructor onsite when you arrive. Limited spots available.

    • TUE 5:15 PM, 6:45 PM
    • THU 5:15 PM, 6:45 PM
    • SUN 11:30 AM, 12:15PM, 2:00 PM, 2:45 PM

  • Roll & Recharge

    TBD

    Find your flow, renew your vibe! Roll & Recharge is a unique wellness experience at Union Winter Roller Express, blending the joy of roller skating with mindful moments to help you reset and recharge. Embrace a fresh start for your mind and body—all in the heart of the city.