Toronto is packed with things to do this weekend, from TIFF and massive cultural festivals to live music, sports, art, food events, and exciting pop-ups. Whether you’re looking for something free, family-friendly, or a fun night out, there’s plenty happening across the city. Here are the best things to do in Toronto this weekend, September 19th–20th, 2026. 

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Best Things To Do This September in Toronto‍

Free Things To Do in September

1. Future

Head over to Future this weekend! Enjoy renowned sounds and lighting, amazing music, and vibes. 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)

When: Fridays & Saturdays

Price: Free + Ticketed‍

Category: 19+

Click here for the website.

2. Toronto International Film Festival (TIFF)

Toronto turns into Hollywood as TIFF brings world premieres, red carpets, celebrity appearances, and highly anticipated films to theatres across the city.‍

Where: Various venues across Downtown Toronto‍

When: Until September 20th, 2026

Price: Refer to TIFF website‍

Category: Family-friendly‍

Click here for the website.

3. Bloor West Village Toronto Ukrainian Festival

Celebrate the festival’s 30th anniversary with a huge parade, Ukrainian food and drinks, craft vendors, cultural pavilions, plus live music and dance performances across multiple stages.

Where: Bloor Street West, from Jane Street to Kennedy Avenue

When: September 18th - 20th, 2026

Price: Free ‍

Category: Family-friendly‍

Click here for the website.

4. Sound on Geary

Geary Avenue transforms into a massive public music festival stretching 1.2 kilometres through the neighbourhood. Explore eight stages featuring live music and creative programming from local venues and businesses.

Where: Geary Avenue, from Ossington Avenue to Primrose Avenue

When: September 19th, 2026 

Price: Free ‍

Category: Date-Friends

Click here for the website.

5. Toronto Tempo Game

Catch the Tempo as they take on the New York Liberty in their final home game of the regular season, featuring a special Fan Celebration Night dedicated to Tempo supporters.

Where: Coca-Cola Coliseum (19 Nunavut Rd)

When: September 20th, 2026 (3 pm)

Price: Refer to Ticketmaster‍

Category: Family-friendly

Click here for the website.

6. Roncesvalles Polish Festival

Celebrate the festival’s 20th anniversary with Polish food and cultural performances, live music across four stages, local vendors, beverage gardens, amusement rides, family activities and a pierogi-eating contest.

Where: Roncesvalles Avenue, Toronto

When: September 19th - 20th, 2026

Price: Free

Category: Family-friendly

Click here for the website.

7.  Smoke-A-Palooza

Join Smoke’s Poutinerie for a 12-hour fan appreciation party featuring free poutine, live ’80s rock tribute bands, daredevil stunts, games, prizes and the World Poutine Eating Championship.

Where: Sankofa Square (1 Dundas St E)

When: September 19th, 2026 (11 am - 11 pm)

Price: Free ‍

Category: Family-friendly

Click here for the website.

8. Queen West Art Crawl

Explore a huge outdoor art festival featuring dozens of local artists, handmade goods, live performances, food vendors and an interactive Kids’ Zone with painting, theatre and creative activities.

Where: Trinity Bellwoods Park (790 Queen St W)

When: September 19th - 20th, 2026

Price: Free

Category: Family-friendly

Click here for the website.

9. Prada Paradoxe Toronto Pop-Up

Step into the world of Prada Beauty and experience the new Paradoxe Sweet Chemistry fragrance. Explore the scent, capture your “Identity in Motion” at an exclusive photo booth and receive complimentary fragrance gifts, custom mementos and exclusive retailer offers.

Where: Upper Ground at The Well (486 Front St W)

When: September 17th - 20th, 2026 (11 am - 7 pm)

Price: Free

Category: Family-friendly

Click here for the website.

10. RELISH The Foodie Event

Get ready to feast at this free 3-day outdoor food festival, featuring 22 food trucks and tents, 30+ local vendors at the Taste & Makers’ Marketplace, live entertainment, hands-on workshops, and family-friendly fun. Try exclusive $10 RELISH Bites and cast your vote for the Most RELISHed Bite of 2026.

Where: Cloverdale - North Parking Lot (250 The East Mall)

When: September 18th - 20th, 2026

Price: Free

Category: Family-friendly

Click here for the website.

11. Toronto Argonauts Game

Cheer on the Argos as they face the Edmonton Elks during their first WWE-themed game. The first 7,000 fans will receive Jey Uso sunglasses.

Where: BMO Field (170 Princes’ Blvd)

When: September 19th, 2026 (3 pm)

Price: Refer to Ticketmaster

Category: Family-friendly

Click here for the website.

12. Anatolia Fest

Experience the vibrant culture and flavours of Türkiye with Turkish cuisine, traditional arts, live music, cultural performances, hands-on activities, a Turkish book fair and more.

Where: Sankofa Square (1 Dundas St E)

When: September 20th, 2026 (12 pm - 8 pm)

Price: Free

Category: Family-friendly

Click here for the website.