Looking for things to do in Toronto this week? From August 31st to September 5th, the city is packed with exciting activities, entertainment, and experiences for everyone. Whether you’re planning a date, hanging out with friends, or looking for family-friendly activities, there’s plenty to check out across Toronto. Here are some of the best things happening this week.

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Best Things to Do in September
Free Things To Do in September

1. Canadian International Air Show

Watch military and civilian aircraft perform over Toronto’s waterfront at the 77th annual air show. The 2026 lineup includes the Canadian Forces Snowbirds, USAF F-16 Demo Team, CF-18 Demonstration and more.

Where: Ticketed zone at Marilyn Bell Park (1095 Lake Shore Blvd W)

When: September 5th - 7th, 2026 (12 pm - 3:40 pm daily)

Price: Free & ticketed options available

Category: Family-friendly

Click here for the website. 

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2. Pitbull: I’m Back Tour

Dance along to Pitbull’s biggest party anthems as his high-energy tour hits Toronto with special guest Lil Jon.

Where: RBC Amphitheatre (909 Lake Shore Blvd W)

When: September 5th, 2026 (8 pm)

Price: Refer to Ticketmaster

Category: Date-Friends

Click here for the website. 

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3. Toronto Dragon Festival

Celebrate Chinese culture with high-pole lion and dragon dances, the Toronto debut of Chaoshan Yingge Dance, multicultural performances, Asian street food, light and water shows, and an interactive AI and robotics showcase.

Where: Nathan Phillips Square (100 Queen St W)

When: September 4th - 6th, 2026

Price: Free

Category: Family-friendly

Click here for the website. 

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4. Toronto International BuskerFest

Toronto’s BuskerFest returns for Labour Day weekend with four days of incredible street performers, including acrobats, musicians, comedians, and fire performers.

Where: Woodbine Park (1695 Queen St E)

When: September 4th - 7th, 2026

Price: Starting at $10

Category: Family-friendly

Click here for the website.

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5. Chris Stapleton’s All-American Road Show

Catch country superstar Chris Stapleton live in Toronto, joined by special guests Zach Top and Ashley McBryde.

Where: Rogers Stadium (105 Carl Hall Rd)

When: September 1st, 2026 (6 pm)

Price: Refer to Ticketmaster

Category: Date-Friends

Click here for the website.

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6. Toronto FC vs. Chicago Fire FC

Cheer on Toronto FC as they face Chicago Fire FC, with match tickets also including free admission to the CNE.

Where: BMO Field (170 Princes' Blvd)

When: September 5th, 2026 (7:30 pm)

Price: Refer to Ticketmaster

Category: Family-friendly

Click here for the website.

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7. Bark in the Park TO

Celebrate all things canine with pet vendors, obstacle courses, play and splash zones, photo opportunities, a costume contest and daily performances by The Canine Circus.

Where: Woodbine Park (1695 Queen St E)

When: September 4th - 7th, 2026

Price: Tickets include access to Buskerfest

Category: Family-friendly

Click here for the website.

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8. RÜFÜS DU SOL: North America 2026

Experience RÜFÜS DU SOL’s atmospheric electronic sound live in Toronto, with special guest Fcukers.

Where: Rogers Centre (1 Blue Jays Way)

When: September 5th, 2026 (7:30 pm)

Price: Refer to Ticketmaster

Category: Date-Friends

Click here for the website.

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9. OH HENRY! Grumble-Activated Vending Machine

Put your stomach grumble to the test at OH HENRY!’s first-ever grumble-activated vending machine for a chance to receive a free chocolate bar.

Where: Union Station, Bay Concourse (65 Front St W)

When: September 1st – 3rd, 2026 (7 am – 7 pm)

Price: Free

Category: Family-friendly

Click here for the website.

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10. Ilana Glazer Live!

Catch comedian, actor and Broad City co-creator Ilana Glazer live in Toronto for a night of stand-up comedy. This show is for ages 15 and up.

Where: Elgin Theatre (189 Yonge St)

When: September 1st, 2026 (7 pm)

Price: Refer to Ticketmaster

Category: Date-Friends

Click here for the website.

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11. TLC & Salt-N-Pepa: It’s Iconic Tour

Catch ’90s music icons TLC and Salt-N-Pepa live in Toronto, joined by special guest En Vogue.

Where: RBC Amphitheatre (909 Lake Shore Blvd W)

When: September 2nd, 2026 (7:30 pm)

Price: Refer to Ticketmaster

Category: Date-Friends

Click here for the website.

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12. T.U. Jazz Fest

Enjoy three days of free live music across two outdoor stages, featuring more than 130 musicians, Grammy and JUNO-recognized talent, emerging artists, masterclasses and a Kids Zone. The festival is family- and pet-friendly.

Where: Mel Lastman Square (5100 Yonge St)

When: September 4th - 6th, 2026

Price: Free 

Category: Family-friendly

Click here for the website.

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13. Music in the Square

Enjoy a free evening of live music presented by Waveland, featuring a curated mix of emerging artists and homegrown favourites.

Where: Sankofa Square (1 Dundas St E)

When: September 3rd, 2026 (6 pm - 10 pm)

Price: Free

Category: Date-Friends

Click here for the website.

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14. St. James Park Selections

Enjoy a free outdoor concert series featuring local musicians every Thursday in September. Grab a seat near the stage or bring a blanket for the back lawn.

Where: Michael Comstock Pavilion at St. James Park (120 King St E)

When: Thursdays, September 3rd - 24th, 2026 (4 - 6 pm)

Price: Free

Category: Family-friendly

Click here for the website.

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