This week in the city offers a fun mix of events, from nostalgic trips into the past to exciting new experiences. Step back into the roaring twenties at Gatsby Redux, or discover timeless style at the Toronto Vintage Show. For something fresh, savour the flavours of the Toronto Garlic Festival, experience new art at the Toronto Biennial of Art, or take in the dazzling Halloween Nights of Lights.
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Much Memories of 299 Queen St W
This special historical walking tour event invites you to step back in time to the era of MuchMusic — exploring the history of the iconic MuchMusic station and the legendary building at 299 Queen St W. Take a walk with Toronto historian Jeremy Hopkin and author Cam Gordon (writer of Track Changes) and learn about how MuchMusic changed Canadian music culture and television broadcasting. Don’t miss this unique opportunity to explore a building you may pass by often on Queen Street and learn about how it served as the epicentre for decades of media memories, pop-culture history, and architectural innovation. More info.
When: September 23
Where: 299 Queen St W.
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Second Summer Festival
Second Summer Festival is a brand-new, multi-venue music festival in Toronto’s West End. Taking place at multiple iconic music venues, this festival is built by music people, for music people, encouraging music discovery and offering a wide selection of musicians, both established and emerging. Enjoy performances from Folk Bitch Trio, W.I.T.C.H., Bells Larsen, Rachel Bobbitt, and so much more on multiple stages like The Mod Club, Monarch Tavern and more. More info.
When: September 24-26
Where: Various locations
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What The Festival
Toronto’s weirdest live comedy festival is back for another year of wild, wonderfully absurd performances guaranteed to entertain, surprise, and make you say, “WTF?” — in the best possible way. From the bizarre to the brilliant, What The Festival promises hilarious clown acts, fabulous drag shows, playful puppet showcases, and so much more. Come celebrate a colourful cast of imaginative “strange-makers” bringing their unique worlds to life through independent stagecraft, DIY design, unconventional comedy, and extraordinary character-driven performances. More info.
When: September 24-27
Where: Various locations
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Just For Laughs Toronto
Just For Laughs returns to the city for nine days of nonstop comedy, bringing together everyone from comedy legends and viral sensations to local favourites and international stars. Catch stand-up from major acts like Pete Davidson, Monét X Change, Sasha Velour and more. With performances taking over clubs and prestigious venues across the city, there’s no shortage of reasons to laugh. From international headliners and beloved local stand-ups to live podcasts, theatrical performances and more, Just For Laughs has something for every kind of comedy fan. More info.
When: September 24-October 3
Where: Various locations
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RUTAS International Festival of Performance
RUTAS 2026 offers an array of national and international performances and invites you to imagine the worlds we want to create together. From fantastical visual games to enriching stories, this edition of the festival does not shy away from the difficult, the controversial, and the magical. Enjoy captivating visual theatre, contemporary dance-theatre, workshops, and more at this innovative and diverse theatre festival. More info.
When: September 24-October 4
Where: Various locations
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Halloween Nights of Lights + Pumpkinville
The perfect way to get into the Halloween spirit is here! This immersive, walk-through autumn and Halloween festival makes its return with even more to discover. Enjoy the dazzling light displays, vibrant giant pumpkin sculptures featuring over 15,000 real pumpkins, carnival rides and games and plenty of photo ops. Guests can also enjoy the Harvest Haunted Maze — family-friendly in the day and full of terrifying scarers at night! Other weekly events include country line dancing, Halloween trivia, live performances, and more. More info.
When: September 25-November 1
Where: CF Sherway Gardens
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Runway of Rezilience
Runway of Rezilience returns for a third year for a bigger, bolder and more immersive experience. This Indigenous-led and community-driven event brings Indigenous culture to the centre stage to be celebrated, uplifted, and seen. Experience extraordinary Indigenous artistic expression across multiple disciplines, from fashion, to visual art, to music, to beadwork, to culinary arts, to performance, and more, all in one night. In addition, enjoy the Indigenous marketplace that provides artists, makers, and creative entrepreneurs a space to exhibit and share their work directly with new audiences. More info.
When: September 26
Where: Evergreen Brick Works
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The Word on the Street
The Word on the Street’s 37th annual festival returns to celebrate Canadian and Indigenous books, magazines, and storytelling. Join in the fun with multiple stages featuring conversations, interviews, and live readings with acclaimed and emerging authors. Other features include an open-air marketplace with books and more from top Canadian publishers and independent booksellers, interactive workshops, and family-friendly entertainment. More info.
When: September 26-27
Where: David Pecaut Square
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Toronto Vintage Show
Canada’s largest sale of vintage clothes, accessories and décor is back! Browse through over 125 expert vintage dealers and independent vendors offering curated fashion and unique housewares. Get ready to find some treasures and search for vintage finds alongside fellow vintage lovers! More info.
When: September 26-27
Where: Queen Elizabeth Building at Exhibition Place
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Gatsby Redux
This immersive outdoor dance show brings The Great Gatsby and the Roaring ‘20s to life. Step into the sights and sounds of the Jazz Age with contemporary dance pieces that invite the audience to follow along in a Gatsby-style theatrical experience, where you can move through Harbourfront Centre as the story unfolds around you. Each new location guides you deeper into Gatsby’s world — revealing new scenes, new surroundings, and unexpected moments around every corner. More info.
When: September 26-27
Where: Harbourfront Centre
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Toronto Biennial of Art
Canada’s leading international visual arts event is back, bringing together an exciting lineup of contemporary artists from Canada and around the world to explore this year’s theme, “Things Fall Apart.” Featuring 30+ artists across 12+ venues, this collaborative festival extends beyond the GTA, creating opportunities to discover contemporary art in unexpected places and new ways. Whether you’re an art enthusiast or simply curious to explore something different, everyone is invited to step into the world of contemporary art. More info.
When: September 26-December 20
Where: Various locations
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Toronto Garlic Festival
Head over to Toronto’s historic Allan Gardens for a full day of all things garlic! Discover fresh Ontario garlic and delicious garlicky foods from local farmers and makers, including unique treats and desserts made with Ontario-grown garlic. Stock up on your garlic supply straight from the growers and explore a variety of local products. Plus, enjoy garlic-themed crafts, culture talks, a garlic breath contest, a vampire costume contest, and so much more. More info.
When: September 27
Where: Allan Gardens
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