Toronto has another packed week ahead, with plenty of ways to get out and enjoy the city from September 21st - 26th. From live music and sports to free waterfront events, cultural celebrations, art, comedy, and the first Halloween thrills of the season, there’s something happening for every kind of plan. Whether you’re looking for a fun night out, a family activity, or something different to do this week, here are some of the events worth checking out.

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Free Things To Do in September
Best Things To Do This September in Toronto

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1. Halloween Haunt Begins

Canada’s Wonderland transforms into a scream-filled Halloween experience with terrifying scare zones, haunted mazes, hundreds of monsters, thrilling night rides, and spooky live entertainment.

Where: 1 Canada's Wonderland Dr (Vaughan)

When: September 25th  - November 1st, 2026 (select nights)

Price: Various pass options

Category: Family-friendly

Click here for the website.  

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2. DroneArt Show: Harry Potter

Watch 1,200 drones recreate iconic moments from the Harry Potter films in sync with the original soundtracks and a live electric violinist.

Where: YZD, Former Downsview Airport (590 Wilson Ave)

When: September 25th - 26th, 2026 (8 pm)

Price: Refer to Fever

Category: Date-Friends

Click here for the website. 

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3. Zach Bryan With Heaven On Tour

Zach Bryan brings his With Heaven On Tour to Toronto with special guests Trampled by Turtles and Gabriella Rose.

Where: Rogers Centre (1 Blue Jays Way)

When: September 21st, 2026 (7 pm)

Price: Refer to Ticketmaster

Category: Date-Friends

Click here for the website. 

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4. Toronto Blue Jays vs. Cincinnati Reds

Catch the Blue Jays at Rogers Centre for two home games against the Cincinnati Reds, featuring a Delgado Retro Windbreaker giveaway and Fan Appreciation Weekend.

Where: Rogers Centre (1 Blue Jays Way)

When: September 25th - 26th, 2026

Price: Refer to Ticketmaster

Category: Family-friendly

Click here for the website.

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5. Public Pier

Experience Toronto’s waterfront with live music, food, local vendors, public art and nighttime projections illuminating the Canada Malting Silos.

Where: Marina Quay West (539 Queens Quay W)

When: September 25th - 26th, 2026

Price: Free

Category: Family-friendly

Click here for the website.

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6. WEEZER: The Gathering

Weezer brings The Gathering tour to Toronto with special guests The Shins and Silversun Pickups.

Where: Scotiabank Arena (40 Bay St)

When: September 25th, 2026 (7 pm)

Price: Refer to Ticketmaster

Category: Date-Friends

Click here for the website.

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7. AGO Art Bash

Canada’s ultimate art party returns to the Art Gallery of Ontario for a night of incredible music, bold contemporary art, live entertainment, food, drinks, and immersive experiences celebrating creativity.

Where: Art Gallery of Ontario (317 Dundas St W)

When: September 24th, 2026 (8 pm - 1 am)

Price: $250

Category: Date-Friends

Click here for the website.

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8. Toronto Maple Leafs vs. Ottawa Senators

Catch the Maple Leafs at Scotiabank Arena as they take on the Ottawa Senators in preseason action.

Where: Scotiabank Arena (40 Bay St)

When: September 23rd, 2026 (7 pm)

Price: Refer to Ticketmaster

Category: Family-friendly

Click here for the website.

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9. Toronto Vintage Show

Shop Canada’s largest sale of vintage clothing, featuring fashion from the 1950s to Y2K, plus handbags, jewellery, streetwear, menswear, accessories and vintage décor.

Where: Queen Elizabeth Building at Exhibition Place (180 Princes’ Blvd)

When: September 26th - 27th, 2026

Price: $17 single-day admission

Category: Date-Friends

Click here for the website.

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10. Latin Parade & Hispanic Fiesta 2026

Celebrate Toronto’s vibrant Latin community with a lively parade featuring music, cultural traditions and plenty of Latin pride as it makes its way to Sankofa Square.

Where: Sankofa Square (1 Dundas St E)

When: September 26th, 2026 (10 am - 9 pm)

Price: Free

Category: Family-friendly

Click here for the website.

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11. Randy Feltface: Gimmick

Australian puppet comedian Randy Feltface brings his latest stand-up comedy show, Gimmick, to Toronto.

Where: The Elgin & Winter Garden Theatres (189 Yonge St)

When: September 26th, 2026

Price: Refer to Ticketmaster

Category: Date-Friends

Click here for the website.

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12. Dogsville x TDM Day

Bring your pup to a dog-friendly street festival featuring local vendors, activities and more in the heart of Streetsville.

Where: Streetsville Village Square (213 Queen St S, Mississauga)

When: September 26th, 2026 (12 pm - 5 pm)

Price: Free

Category: Family-friendly

Click here for the website.

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13. AFC Toronto vs. Ottawa Rapid FC

Cheer on AFC Toronto as they take on Ottawa Rapid FC in Northern Super League action at York Lions Stadium.

Where: York Lions Stadium (230 Ian MacDonald Blvd)

When: September 26th, 2026 (2 pm)

Price: Refer to Ticketmaster

Category: Family-friendly

Click here for the website.

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14. National Tree Day Nature Walk

Celebrate National Tree Day in High Park with a guided nature walk exploring the remarkable trees that make Toronto’s urban forests thrive.

Where: High Park Forest School (375 Colborne Lodge Dr)

When: September 23rd, 2026 (6 pm - 7:30 pm)

Price: $10

Category: Family-friendly

Click here for the website.

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