Photo via @thebentway and @milebright_photo on Instagram
We’re just a few days away from the last day of summer — sounds unbelievable, I know. But luckily for us, the weather has been on the warmer side of things, so we’re soaking it all up as much as we can. Good thing there are tons of things to do in Toronto that will keep us outdoors.
Here are 10 of the best things to do this weekend in Toronto.
Support local, explore a number of vendors and art, and enjoy some live music!
When: Friday, Sept. 18, 2026
Time: 3 p.m. to 10:30 p.m.
Where: Green P Parking Lot, 7 Bartlett Ave.
Cost: Free
Kicking off on Sept. 19 and 20, Oktoberfest will take over The Distillery District, welcoming all to enjoy live music and entertainment, themed games, traditions, and, of course, plentiful eats.
When: Saturday, Sept. 19 and Sunday, Sept. 20, 2026
Time: Select time slots
Where: The Distillery Historic District – 55 Mill St.
Cost: $33.90 plus fees
Dubbed Public Pier, this new project transforms Marina Quay West (beside Toronto Music Garden and opposite the Canada Malting Silohs) into a day-to-night destination with public programming that includes food markets, DJs and even line dancing.
When: Friday, Sept. 18 and Sunday, Sept. 19, 2026
Time: 1 p.m. to 11 p.m.
Where: Marina Quay West, 539 Queens Quay W.
Cost: Free
Get your hands on delicious dairy treats and go home with limited-edition merch! But before you dip, enjoy the live DJs and milk and cereal rave.
And it’s all a post-to-pay experience/ All you have to do is follow and tag @milkupontario on Instagram or TikTok to build your own tray of dairy eats and drinks for breakfast, lunch, dinner, and even a midnight snack.
You can then exchange a token at the gachapon machine for a prize.
When: Friday, Sept. 18 to Sunday, Sept. 20 and Friday, Sept. 25 to Sunday, Sept. 20
Time: 9 a.m. to 9 p.m.
Where: 938 Queen St. W.
Cost: Free
Barbie is hosting an interactive activation on Sept. 19 and 20 at Yorkdale Shopping Centre with a ton of hands-on opportunities with the new Barbie DreamHouse.
It’s free to attend, and those interested in attending can RSVP online. It’s on a first-come, first-served basis, and you will be invited to join the queue during busy periods. While guests of all ages are welcome, hands-on DreamHouse play is recommended for children ages 3+.
When: Saturday, Sept. 19 and Sunday, Sept. 20, 2026
Time: Saturday from 10 a.m. to 9 p.m.
Where: Yorkdale Shopping Centre – 3401 Dufferin St.
Cost: Free
Aww, Kyle Lowry, how we love you! To honour and celebrate Lowry, the Toronto Raptors are hosting a free party with food and drink stations, exclusive merch, on-stage programming, and a ton more.
When: Saturday, Sept. 19, 2026
Time: 11:30 a.m. to 11 p.m.
Where: Maple Leaf Square – 15 York St.
Cost: Free
Cheatin’ Hearts is bringing the country fun to The Well with a night of music, dancing, and fun. No experience is necessary; whether you’re new or jumping back into action, enjoy an evening of line dancing with step-by-step lessons.
When: Friday, Sept. 18, 2026
Time: 6:30 to 8:30 p.m.
Where: The Well, Lower Ground – 486 Front St W.
Cost: Free
A free street festival is taking over a portion of Geary Ave with a ton of stages, live music, street art, local food, and drinks!
When: Saturday, Sept. 19, 2026
Time: 1 p.m. to late
Where: Geary Ave from Ossington Ave to Primrose Ave
Cost: Free
Enjoy the last few days of the Toronto International Film Festival as it marks 51 years in the industry. This is your chance to catch a last-minute flick!
When: Until Sunday, Sept. 20, 2026
Time: Varies
Where: King Street, several theatre locations
Cost: Free
After weeks of FIFA World Cup action, Toronto’s The Bentway is back to business, opening up its 200-metre skating trail for another season of roller skating under the Gardiner.
Not only will you be able to enjoy some skating action this summer, but you will also be able to take part in a series of community-driven events. These include skate parties, beginner lessons, art workshops, family programming, and the launch of a brand-new after-school program for young city-builders.
When: Until Sunday, Sept. 27, 2026
Time: Fridays from 5 to 9 p.m., Saturdays and Sundays from 1 to 8 p.m.
Where: The Bentway Skate Trail — 250 Fort York Blvd.
Cost: Skating is free; rentals start at $18 (plus tax)
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