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Olivia Rodrigo, Sleeping With Sirens, and Loreena McKennitt headline Toronto concerts this week

Live music fans are in for a treat with plenty of concerts to catch in Toronto this week. From arena pop to pop-punk, there’s a show for everyone.

Female singer on stage in pink dress alongside band members in backstage area, promoting Toronto concerts this week.
Weezer and Tove Lo are two artists playing shows in Toronto this week. (Courtesy: IG/oliviarodrigo/sleepingwithsirens)

What to know

  • Olivia Rodrigo, Sleeping With Sirens and Loreena McKennitt are among the biggest artists performing in Toronto this week.
  • Concerts run from Oct. 26 to Nov. 1 at venues including Scotiabank Arena, HISTORY, and Massey Hall
  • Tickets are still available for many shows, with prices starting at around $70 depending on the event.

Welcome in the chillier fall weather in Toronto with another exciting week of concerts at venues around the city, including two highly anticipated concerts at Scotiabank Arena by resident pop girl Olivia Rodrigo, and pop-punk shows headlined by The Story So Far and Sleeping With Sirens.

From arena pop to pop-punk, concert lovers will have plenty of opportunities to catch a show or two around the GTA in the coming days.

Here are some of the artists performing in Toronto this week:                                          

Olivia Rodrigo

  • When: Oct. 26 and 27
  • Where: Scotiabank Arena

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Gen Z’s favourite pop star Olivia Rodrigo will be performing Monday and Tuesday night at Scotiabank Arena. She’ll be bringing her critically acclaimed third album, You Seem Pretty Sad for a Girl So in Love, along with her biggest hits, to Toronto. 

Rodrigo is one of the most successful artists of the 2020s, as all three of her studio albums (Sour, Guts and You Seem Pretty Sad for a Girl So in Love) have topped the Billboard 200. She has three Grammy Awards, five MTV Video Music Awards, and was named Time’s Woman of the Year in 2022. 

Songs you might know: “Drop Dead,” “The Cure,” “Vampire,” “Drivers License,” and “Deja Vu.”

Tickets for Rodrigo’s two concerts at Scotiabank Arena’s are sold out.

Periphery

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  • When: Oct .26
  • Where: HISTORY

American progressive metal band Periphery will be taking the stage at HISTORY Monday night on A Pale White Dot tour to support their eighth album of the same name. Formed two decades ago in Washington D.C., the band are considered the one of the founders of progressive metal’s “djent” moment.

Periphery has released eight self-produced studio albums, including, A Pale White Dot, which came out in May 2026. The band is known for using non-traditional guitar tunings in their songs — most commonly drop tuning, 8-string, and 7-string tunings.

Songs you might know: “Marigold,” “Reptile,” “Stranger Things,” and “The Bad Thing.”

Tickets are still available for Periphery’s show at HISTORY, with general admission starting at $72.66

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The Story So Far

When: Oct. 28

Where: HISTORY

Californian fourth-wave pop-punk band The Story So Far will be opening up the mosh pit at HISTORY this Wednesday with two other heavyweights in the scene, The Starting Line and Ultra Q. This is the first time they’ve returned to the Toronto stage in over a decade, having last headlined a show in 2016 at The Mod Club.

The Story So Far is one of the most popular pop-punk bands that formed in the late-2000s and have amassed a dedicated following. To date, they’ve released five albums, six EPs, and a handful of singles. The band’s sophomore album, What You Don’t See, is widely considered their magnum opus and was ranked #9 by Rolling Stone on its list of The 50 Best Alums of 2013.

Songs you might know: “Clairvoyant,” “Nerve,” “Empty Space,” and “Things I Can’t Change.”

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Tickets for The Story So Far’s concert at HISTORY are sold out, but keep an eye on Ticketmaster for occasional verified resale tickets.

Loreena McKennitt

When: Oct. 31 and Nov. 1

Where: Massey Hall

Legendary Canadian singer-songwriter Loreena McKennitt will be celebrating the 30th anniversary of her fifth album, The Mask and Mirror at Massey Hall this weekend. 

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McKennitt first took a chance in music in 1985, four years after joining the Stratford Festival acting company in Stratford, Ont. From 1985 to 1998, the Manitoba-native self-released six studio albums, ending with 1997’s The Book of Secrets. All of her work is under her own label, Quinlan Road. After a decade-long hiatus, McKennitt returned with An Ancient Muse in 2006. 

In 2023, she was inducted into the Canadian Songwriters Hall of Fame. In 2025, she was inducted into the Canadian Music Hall of Fame.

Songs you might know: “The Mummer’s Dance,” “The Mystic’s Dream,” “Tango to Evora,” and “Dante’s Prayer.”

Tickets for McKennitt’s two shows at Massey Hall are on sale starting from $76.80.

Sleeping With Sirens

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  • When: Nov. 1 
  • Where: HISTORY

A second mainstay in the pop-punk and emo scene will be bringing the house down in Toronto this week. Floridian post-hardcore band Sleeping With Sirens will be playing HISTORY Sunday evening to support their eighth studio album, An Ending in Itself. 

Sleeping With Sirens rose to fame in 2010 with the song, “If I’m James Dean, You’re Audrey Hepburn” but it was their sophomore album, Let’s Cheers to This that really put them on the map. The group is fronted by Kellin Quinn, whose high-pitched vocals sets the band apart from their peers. 

Songs you might know: “If You Can’t Hang,”, “Better Off Dead,” “If I’m James Dean, You’re Audrey Hepburn,” and “Kick Me.”

General admission tickets for Sleeping With Sirens’ concert at HISTORY are still on sale for $70.83.

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