In one of those Toronto moments, our homegrown Grammy-winning R&B artist Daniel Caesar surprised fans on Saturday with a free pop-up concert in the heart of the city at Trinity Bellwoods Park.

At around 3 p.m., Caesar posted a cryptic Instagram story that simply read: “Toronto. Trinity Bellwoods. Five o’clock.” That was all it took.

 

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Within two hours, thousands of fans had made their way to the park’s iconic dog bowl area, creating a festival-like atmosphere with barely any warning. It was part of Caesar’s low-key pop-up tour in support of his upcoming fourth studio album, Son of Spergy, set to drop on Oct. 24.

As he entered the park, Caesar was flanked by security and long-time friend and collaborator, Mustafa the Poet. But even with a security presence, there was no real barrier between the artist and his fans — and that made the experience even more intimate and unique. Where else could something like this happen?

 

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Videos from the event were all  over social media, showing fans climbing trees, running across the park and even bringing a ladder to get a better view of the performance. One person reportedly offered Caesar the ladder so he could sing from a higher vantage point and be seen by more of the massive crowd.

 

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Performing with just his guitar, Caesar delivered stripped-down renditions of his hits, including his Grammy-winning song “Best Part.”

 

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Toronto wasn’t the only city to get a taste of Caesar’s impromptu shows. On Sunday, he made a similar appearance in Montreal, performing for a crowd at Parc Des Hirondelles. Though smaller in scale, the Montreal concert carried the same DIY spirit.

Between the surprise announcements, intimate performances, and strong hometown turnout, Daniel Caesar has clearly struck a chord with fans leading up to his album release. And he will no doubt be back when he tours in support of the new record. If Son of Spergy is anything like his recent shows — expect honesty, soul, and a little bit of magic.

We’re just days away from the much-anticipated release of Taylor Swift’s 12th studio album, The Life of a Showgirl. When the full album drops on Oct. 3, why not be among friends and Swifties to celebrate? Check out these album release parties in Toronto, from dance parties to drag shows.

Taylor Swift: The Life of a Showgirl Album Release Party

When Taylor Swift’s 12th album releases on Oct. 3, Bar Cathedral will be honouring the occasion with a party — listen to the new album in full, then have a dance party to music from all eras. Prepare to sparkle with a friendship bracelet-making station, glowsticks, glittery drinks and more.

Tour of a Showgirl Toronto Release Party

TSwift Dance Party Canada is back with another iconic event: a TS12 launch party at Dprtmnt, run by fans, for fans. This party will be more than just The Life of a Showgirl. Enjoy top hits and deep cuts from every era all night long. Happening on Saturday, early bird tickets for this event have already sold out, so act fast!

The Life of a Showgirl Release Party and drag show

Drag performers plus Taylor Swift is a match made in heaven — especially when Tay BoBo, Toronto’s own TSwift drag impersonator, is around. Celebrate the album at the Drink with a listening party hosted by Swiftie sisters Tay BoBo and Sapphyre Poison, featuring live (and hilarious) reactions to the full album. Arrive at 11 p.m. on Oct. 2 and listen in real time at midnight when the album drops!

The Official Release Party of a Showgirl

T.Swift thinks of everything — she even created her own official release party for the occasion! The Official Release Party of a Showgirl is an 89-minute theatrical experience tied to Swift’s latest album, and Swifties from across the world can watch the release in theatres from Oct. 3–5. You can snag advance tickets at your closest theatre here. 

Taylor Swift Dance Party 

Swifties Socials is back with another event — what they’re calling the Biggest Taylor Swift Dance Party in Toronto. Celebrate the album release on Oc. 3 among over 500 Swifties, where you can dance, sing and cry to the new music — plus some deep cuts, remixes and hidden gems.

Taylor Swift Brunch: Trivia & New Album

If the nightclub isn’t really your thing, head to Snakes and Lattes College on Oct. 4 for a Taylor Swift Brunch, trivia and listening party! Promising a trivia experience that is an “immersive journey through Taylor’s world,” including anagrams, crosswords and more, you can also create your own friendship bracelet and shop Swiftie-inspired goods from local vendors.

The Life of a Showgirl Paint & Listen Party

Dust off your artistic skills for this paint and listen party! Happening on Oct. 11, you’ll spend this paint night listening to the album from start to finish while you paint on a showgirl-inspired canvas. When the night is over, you’ll gain intimate knowledge of The Life of a Showgirl and your very own Swift-themed canvas to commemorate the new era!

Sept. 30 is the National Day for Truth and Reconciliation and Orange Shirt Day in Canada. It’s a day that honours the lost children and the survivors of residential schools in Canada, as well as their families and communities.

It’s a day to wear the colour orange, which begins with the story of Phyllis Webstad, a Northern Secwepemc (Shuswap) from the Stswecem’c Xgat’tem First Nation, who wore an orange shirt on her first day at a church-run residential school. It was taken from her by school authorities, and has become a symbol to raise awareness about the cultural genocide that took place through the country’s residential school system.

It’s important for us to be aware of our history and work towards reconciliation. Here are a few resources to help residents of Toronto educate themselves on the culture and history of Indigenous communities on this day of reflection.

Indigenous Voices, ROM

As part of their At Home programming, the Royal Ontario Museum’s Indigenous Voices series features live webinars twice a month to share stories and celebrate Indigenous culture. Designed for elementary and high school students and educators, the program highlights distinct ancestral objects and offers activities to engage viewers. The program is free and ranging in topic from cultural dance to storytelling can be watched anytime online.

The Native Canadian Centre of Toronto

The Native Canadian Centre of Toronto (NCCT) is a charitable organization that works to support the wellbeing of Toronto’s Indigenous community. Their beautiful downtown heritage building offers services and programs based on Indigenous traditions and teachings. Refer to their website for a list of programs available for Indigenous and non-Indigenous members, such as Indigenous Cultural Competency Training (and consider donating to support their cause!). Inside is the Cedar Basket Giftshop, which carries a wide selection of First Nations, Metis and Inuit handcrafted products including original art, jewelry, moccasins, beadwork, carvings and more – shop there to support Indigenous artist and the NCCT.

Indigenous Celebrations, Toronto Public Library

The Indigenous Celebration program running at the Toronto Public Library is a festival of culture featuring webinars on storytelling and literature from First Nations, Metis and Inuit heritage. Upcoming programs include three different screenings on the National Day of Truth and Reconciliation, including the 2024 documentary The Stand, and an Indigenous medicine music experience with Anishinaabe artist Aqua Nibii Waawaaskone. The library also provides literary education through collections of Indigenous reading, including books that explore important elements of Canadian history, such as the traumas of residential school systems.

Woodland Cultural Centre

Located in Brantford on the site of a former residential school, taking a day trip to the Woodland Centre is a great opportunity to learn about Indigenous culture through interactive museum exhibits both indoors as well as outdoors on the five-acre grounds. This year, the centre is unveiling the Mohawk Institute Residential School as an Interpretive Historic Site on the National Day for Truth and Reconciliation. They’ll be offering a day of Orange Shirt Day programming, including an opening ceremony, art activity, screenings of Silent No More and atalk and Q&A with survivors

Reconciliation Walk, Village at Black Creek

On Sept. 28, visit the Village at Black Creek for a Reconciliation Walk and Indigenous Art Trail, created in partnership with humanitarian Indigenous-focused charity True North Aid. Visitors can follow the self-guided Reconciliation Walk to learn more about the residential School system, view art installations created by local and Indigenous artists, take part in reflection and art-based activities and consider the Truth and Reconciliation Committee’s 94 Calls to Action throughout the village. 

Indigenous Cinema, National Film Board of Canada

The National Film Board of Canada’s collection of Indigenous-made films is available to stream for free on their Indigenous Cinemas page. The platform offers old, new and classic films in a variety of styles including fiction, documentary, animation and educational. Support Indigenous talent by watching the work of top directors or educate yourself through a selection of Indigenous subjects including culture and literature, rights, nature and community.

Gord Downie & Chanie Wenjack Fund

The Gord Downie & Chanie Wenjack Fund (DWF) is a registered charity located an hour outside of Toronto that works to create a better path for Indigenous Peoples of Canada by educating, connecting and spreading awareness. For National Day of Truth and Reconciliation, the Gord Downie & Chanie Wenjack Fund is partnering with local and national media outlets and radio station on Sept. 30 for the fourth annual “A Day to Listen,” featuring the voices and stories of Indigenous people from 6 a.m. to 6 p.m. This year also marks the 10th anniversary of the Truth and Reconciliation Commission of Canada’s final report and its 94 calls to action. To honour this anniversary, DWF is running a series of live YouTube episodes, such as one titled Living Reconciliation on Sept. 29 with community leaders and champions Harriet Visitor and Melissa Mollen Dupuis and another titled Shaping Tomorrow on Sept. 30 with young leaders Raven MacLeod-Johnson and Trevor Ng. 

Coming up in 2026:

ImagineNATIVE Film + Media Arts Festival

Toronto’s imagineNATIVE Film + Media Arts Festival has changed its festival date permanently, moving the week-long festival to June 2026, in time for Indigenous Peoples’ Month. This will be its 26th annual event celebrating and promoting a greater understanding of Indigenous peoples and cultures through film, video, audio and digital media. The arts festival is the world’s largest presenter of Indigenous screen content, and in previous years it showcased over 125 works from artists, representing 13 countries in over 41 Indigenous languages in a hybrid format with in-person and virtual events. The festival runs June 2–7 in-person in Toronto and June 8–14 online.

The hottest shows in Toronto this month include the return of Ryan Reynolds, Talking Heads icon David Byrne, Icelandic-Chinese musician Laufey, Nuit Blanche and much more

Festival of Authors

The Toronto International Festival of Authors runs Oct. 29 to Nov. 2 at Victoria University with more than 100 conversations, masterclasses, talks, and readings, featuring authors such as Rachel Maddow, Rebecca Solnit, Kiran Desai, and Madeleine Thien.

Ryan Reynolds

Join Ryan Reynolds and special guests for John Candy: I Like Me – An Evening with Ryan Reynolds & Friends on Monday, Oct. 6, at Queen Elizabeth Theatre in Toronto, an all-ages screening of the new John Candy documentary.

Childish

Tarragon Theatre is set for the Toronto premiere of CHILD-ish (Oct. 21 to Nov. 16), a witty and heartfelt verbatim theatre production where four adult actors perform the exact words of forty children reflecting on love, life and the world.

Laufey

Grammy-winning Icelandic-Chinese multi-instrumentalist Laufey brings her A Matter of Time Tour with special guest Suki Waterhouse to Toronto’s Scotiabank Arena on Oct. 19 and 20, in support of her upcoming album A Matter of Time.

David Byrne

David Byrne brings An Evening with David Byrne: Who Is the Sky? Tour to Massey Hall in Toronto for three nights, Oct. 21–23, celebrating his new album Who Is the Sky? with special appearances from musical collaborators, including St. Vincent and Hayley Williams.

Hocus Pocus

Disney’s cult classic Hocus Pocus, starring Bette Midler, gets the full concert treatment at Meridian Hall, Oct. 17–18, with the TO Live Orchestra performing the beloved score live to picture — just in time for Halloween.

Jesse Welles

Jesse Welles brings his Under The Powerlines Tour to Toronto’s Danforth Music Hall on Oct. 18, following the release of his fifth studio album, Devil’s Den, a cabin-recorded collection that continues his poetic folk-rock storytelling.

Tell Tale Harbour

Alan Doyle, of Great Big Sea fame, stars in Tell Tale Harbour, a heartwarming and hilarious East Coast musical about a small town’s big scheme to save itself, running until Nov. 2, at the Royal Alexandra Theatre after a sold-out Charlottetown debut.

Slave Play

Canadian Stage presents the Canadian premiere of Jeremy O. Harris’s Slave Play, a provocative, razor-sharp satire exploring love, race and relationships, running until Oct. 26 at the Berkeley Street Theatre.

Neko Case

Acclaimed singer-songwriter and New Pornographers co-founder Neko Case brings her fearless artistry and lyrical storytelling to Massey Hall on Oct. 20 in support of her new album Neon Grey Midnight Green, with opener Des Demonas.

Roméo et Juliette

Roméo et Juliette plays at Toronto’s Four Seasons Centre until Oct. 18, reimagining Shakespeare’s tale in Gilded Age New York, featuring Gounod’s sweeping score, the COC Orchestra and Chorus and a cast of magical performers.

GoGo Penguin

GoGo Penguin, the Manchester trio fusing jazz, classical and electronic influences, makes its  Koerner Hall debut on Oct. 18, with music from its new album, Necessary Fictions, as part of the Royal Conservatory’s Pop & Beyond series.