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Toronto is packed with things to do this September! From major concerts and sports games to festivals, live entertainment, markets, and family-friendly events, here are some of the best things happening across the city.
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1. Pitbull—I'm Back! With Special Guest Lil Jon
Mr. Worldwide is back in Toronto! Pitbull takes over with special guest Lil Jon, bringing massive party anthems and throwback hits.
Where: RBC Amphitheatre (909 Lake Shore Blvd W)
When: September 5th, 2026 (8 pm)
Price: Refer to Ticketmaster
Category: Date-Friends
2. Future
If you’re looking for something fun to do in the city in September, check out Future. Experience one of Toronto's top nightlife destinations, featuring world-class sounds and lighting, exciting weekly events, and a 4 am last call. Plus, enjoy free entry before 11:30 pm every Friday and Saturday, along with complimentary prosecco with a purchase of a birthday package.
Where: Future (570 Queen St W, Toronto, ON M5V 2B5)
Price: Free + Ticketed
Category: 19+
3. Taste of the Kingsway
South Etobicoke's largest street festival returns this September! Presented by Mantella Corporation, Taste of the Kingsway is a free 3-day festival featuring delicious food, live music, family-friendly entertainment, local vendors, and plenty of activities for all ages. It's the perfect way to celebrate the end of summer, so mark your calendars.
Where: Bloor Street West between Montgomery Rd and Prince Edward Dr
When: September 11th-13th, 2026
Price: Free admission
Category: Family-friendly
4. Toronto Blue Jays Games
Watch the Toronto Blue Jays live, cheer them on, and grab some ballpark food while taking in the electric atmosphere with the CN Tower right next door.
Where: Rogers Centre (1 Blue Jays Way)
When: Various games throughout September
Price: Refer to Ticketmaster
Category: Family-friendly
5. Zach Bryan—With Heaven On Tour
Catch the country star live with his signature mix of raw storytelling, fan-favourite songs, and high-energy performances.
Where: Rogers Centre (1 Blue Jays Way)
When: September 21st – 22nd, 2026 (7 pm)
Price: Refer to Ticketmaster
Category: Family-friendly
6. Canadian International Air Show
Toronto’s skies come alive as the Canadian International Air Show returns for its 77th year with military jets, vintage aircraft and thrilling aerobatic performances, including the Canadian Forces Snowbirds.
Where: Marilyn Bell Park / Toronto Waterfront
When: September 5th - 7th, 2026 (12 pm - 3:40 pm daily)
Price: Exclusive Air Show Zone tickets available; show can also be seen from some areas of the CNE
Category: Family-friendly
7. TLC & Salt-N-Pepa with En Vogue: IT’S ICONIC
TLC, Salt-N-Pepa and En Vogue are bringing their iconic hits to Toronto for one huge night of ’90s and R&B nostalgia.
Where: RBC Amphitheatre (909 Lake Shore Blvd W)
When: September 2nd, 2026 (7:30 pm)
Price: Refer to Ticketmaster
Category: Date-Friends
8. Toronto Maple Leafs Preseason
Cheer on the Leafs and get an early look at the team before the regular season begins.
Where: Scotiabank Arena (40 Bay St)
When: Various dates in September
Price: Refer to Ticketmaster
Category: Family-friendly
9. Toronto Vintage Show
Canada’s largest vintage clothing sale returns to Toronto. Shop everything from 1950s fashion to Y2K finds, plus vintage handbags, jewelry, accessories, and home décor.
Where: Queen Elizabeth Building, Exhibition Place (180 Princes’ Blvd)
When: September 26th - 27th, 2026
Price: $17 single-day admission at the door
Category: Family-friendly
10. Ilana Glazer Live!
Best known for co-creating and starring in Broad City, Ilana Glazer brings her live stand-up show to Toronto.
Where: The Elgin & Winter Garden Theatres (189 Yonge St)
When: September 1st, 2026 (7 pm)
Price: Refer to Ticketmaster
Category: Date-Friends
11. 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: Date-Friends
12. Toronto FC vs. Chicago Fire FC
Toronto FC returns to BMO Field for a Saturday night showdown against Chicago Fire FC. Catch the action live as the Reds battle it out in front of the home crowd.
Where: BMO Field (170 Princes' Blvd)
When: September 5th, 2026 (7:30 pm)
Price: Refer to Ticketmaster
Category: Family-friendly
13. Wu-Tang Forever: The Final Chamber
Wu-Tang Clan brings The Final Chamber tour to Toronto for a huge night of hip-hop, joined by Bone Thugs-N-Harmony.
Where: RBC Amphitheatre (909 Lake Shore Blvd W)
When: September 8th, 2026 (7:30 pm)
Price: Refer to Ticketmaster
Category: Date-Friends
14. AC/DC — POWER UP TOUR 2026
Catch the iconic band live as they take over Rogers Stadium with decades of classic hits and legendary rock performances.
Where: Rogers Stadium (81 YZD Ln, North York)
When: September 16th, 2026 (7 pm)
Price: Refer to Ticketmaster
Category: Date-Friends
15. Ben Schwartz & Friends
Ben Schwartz brings his fast-paced comedy show to Toronto, joined by comedy friends for a completely improvised performance where no two shows are the same.
Where: Meridian Hall (1 Front St E)
When: September 18th, 2026 (7 pm)
Price: Refer to Ticketmaster
Category: Date-Friends
16. AFC Toronto vs. Calgary Wild FC
Catch some of Canada’s top women’s soccer talent live as Toronto battles Calgary in Northern Super League action.
Where: BMO Field (170 Princes' Blvd)
When: September 6th, 2026 (2 pm)
Price: Refer to Ticketmaster
Category: Family-friendly
17. The National Franchise Show
The National Franchise Show brings franchise brands, experts and aspiring entrepreneurs together for two days of opportunities, networking, and free seminars.
Where: The International Centre (Hall 5, 6900 Airport Rd, Mississauga)
When: September 19th - 20th, 2026
Price: Starting at $15
Category: Family-friendly
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