10+ Things To Do in Toronto This Week (September 21-27)
Still figuring out how to spend the last week of September? Loosen your belt at Etobicoke Ribfest, explore the Toronto Biennial of Art, take your dog on a community walk through Riverside, watch UP with a live orchestra, or sing along with Zach Bryan and Weezer. I’ve put together this guide to things to do in Toronto this week (September 21–27) to help you find festivals, concerts, art events, family activities, and plenty of ways to make the most of the week. By the time you reach the end of this list, you may have more plans than free time.
Editor’s Note: Keep an eye on official event pages, as details can sometimes change. Some free events require an RSVP, so double-check those ahead of time. Also, bring cash or have a digital payment method ready for any fun finds on-site.
Things to Do in Toronto This Week: 12 Epic September Events
Food, Festivals & Community Events
Etobicoke Ribfest
September 25-27, 2026丨Colonel Sam Smith Park丨Free entry with $5 charitable donation suggested
If food festivals in Toronto sit high on your weekend priority list, Etobicoke Ribfest makes an easy choice. It fills Colonel Sam Smith Park with award-winning rib teams serving smoked ribs, brisket, pulled pork, BBQ chicken, sausage, and those giant dinosaur-sized beef ribs. You’ll also find live music, artisan vendors, cold drinks, a kids’ zone, and face painting throughout the weekend.
Art, Film & Creative Events
Toronto Biennial of Art
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September 26-December 20, 2026丨Various venues丨Free
If you like discovering new corners of the city without spending money, you’ll want to add the Toronto Biennial of Art to your list of free things to do in Toronto. This city-wide exhibition features newly commissioned works by artists responding to Toronto’s communities, histories, and landscapes. Installations appear across multiple venues, giving you a reason to explore corners of the city you may not visit often.
Gatsby Redux – Mixed eMotion Theatrix
September 26-27, 2026丨Harbourfront Centre丨Ticket info coming soon
This week, it’s the perfect excuse to bring out that vintage outfit sitting in your closet. The Roaring Twenties return to Harbourfront Centre with an outdoor dance performance inspired by The Great Gatsby. Performers in period costumes guide audiences through a theatrical experience set to Jazz Age classics and electro swing music.
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Mari Törőcsik Hungarian Film Festival
September 24-27, 2026丨Paradise Cinema and Carlton Cinema丨Ticketed
Prefer movie nights with stories you rarely get the chance to see on Canadian screens? Add this film festival to your calendar. This year’s festival celebrates acclaimed Hungarian actress Mari Törőcsik while showcasing significant Hungarian films from 2025 and 2026. It is also a great introduction to the growing international film festival Toronto scene.
Dog-Friendly Plans & Family Fun
Dogsville x TDM Day
September 26, 2026丨Streetsville Village Square, Mississauga丨Free
Your pup may end up having a busier social life than you this weekend. Dogsville arrives in Streetsville with local vendors, treats, and activities designed for four-legged guests. This pet-friendly event also celebrates Toronto Dog Mom Day, so prepare for plenty of adorable photo ops and an impressive number of wagging tails.
Toronto Dog Moms X Riverside BIA: Paws Walk
September 27, 2026丨657 Queen Street East, Toronto丨Ticketed
Need a slower-paced Sunday activity? Grab a leash and join fellow dog owners for a community walk through Riverside. The route highlights local businesses, historic streets, and pet-friendly patios while giving both humans and dogs a chance to socialize. It’s a fun outing where your dog will make more friends than you do.
Can’t-Miss Concerts This Week
Zach Bryan – With Heaven On Tour
September 21-22, 2026丨Rogers Centre
Country music’s biggest storyteller heads to Rogers Centre for his massive With Heaven On Tour. Known for songs like “Something in the Orange,” “I Remember Everything,” and “Oklahoma Smokeshow,” Zach Bryan has built a reputation for raw songwriting and stadium-sized sing-alongs. If you’ve spent months hearing his music on playlists, this is your chance to hear those songs echo across one of Toronto’s largest venues.
Staind – Break The Cycle Anniversary Tour 2026
September 21, 2026丨RBC Amphitheatre
Feeling nostalgic for early-2000s rock? Staind celebrates 25 years of Break The Cycle with a performance featuring classics like “It’s Been Awhile,” “Fade,” and “For You.” Seether, Hoobastank, and Hinder join the lineup, making this one of the must-attend Toronto concerts this week.
Weezer – The Gathering Tour
September 25, 2026丨Scotiabank Arena
You know an audience is invested when thousands of people enthusiastically sing along to a song about a sweater. Weezer returns to Toronto with The Gathering Tour, supported by The Shins and Silversun Pickups. Along with new material, expect classics like “Buddy Holly,” “Island in the Sun,” and “Beverly Hills” to get plenty of airtime.
BØRNS with Two Feet & The Blue Stones
September 25, 2026丨The Bowl at Sobeys Stadium
Want to catch three distinct acts in one massive night of live music in Toronto? BØRNS celebrates ten years of Dopamine, featuring songs like “Electric Love” and “Past Lives.” Two Feet adds his blues-inspired electronic sound, while Canadian rock duo The Blue Stones deliver the guitar-driven energy that earned them multiple JUNO nominations.
Cinemas in Concert
UP in Concert
September 27, 2026丨The Bowl at Sobeys Stadium
There are two types of people attending this event. You either admit the opening montage makes you emotional, or you pretend it doesn’t. Disney and Pixar’s UP screens in full while a live orchestra performs Michael Giacchino’s Academy Award-winning score. If you seek family events in Toronto that appeal to both kids and adults, this is a fun pick.
Ready to refresh your wardrobe?
It’s time to swap your summer clothes for layers and textures. You can explore my guide to Where to Shop Fall Fashion Trends in Toronto to find the top local boutiques for your new look.
Frequently Asked Questions (FAQs)
Etobicoke Ribfest is the biggest food-focused event on the calendar this week, serving ribs, brisket, pulled pork, festival snacks, and drinks. The Ukrainian Festival and Roncesvalles Polish Festival also offer plenty of opportunities to sample traditional dishes while enjoying live entertainment.
Yes. The Toronto Biennial of Art offers free admission across multiple locations. You can also visit Dogsville and several cultural festivals without purchasing admission tickets.
The week features major performances from Zach Bryan, Staind, Weezer, BØRNS, Two Feet, and The Blue Stones. If you’re interested in orchestral performances, UP in Concert also offers a live symphony experience paired with the beloved Pixar film.
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