Get ready for another amazing month in Toronto! October brings so many fun events like Nuit Blanche, Toronto Cocktail Festival, and of course, lots of spooky activities.

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1. Water/Fall Festival

The Water/Fall Festival is a free celebration of arts and culture taking place along Toronto’s waterfront! Experience breathtaking public art installations on land and water, harvest-themed food and drink markets, live music, dynamic dance performances, a sustainable makers market, and magical illuminated boat tours. Mark your calendars because you don’t want to miss this. Find all scheduling and programming details at waterfallfestival.ca.

Where: Queens Quay, from Bathurst St. to Bay St.

When: September 27th-28th and October 4th-5th, 2025

Price: Free admission

Category: Family-friendly

Click here for the website.

2. Nuit Blanche

Nuit Blanche is back for another year of incredible contemporary art. This year’s theme, Translating the City, invites you to consider how art can translate the complexities of cities and the role we all play within them.

Where: Multiple locations

When: October 4th, 2025 (7 pm - 7 am)

Price: Free admission

Category: Date/Friends

Click here for the website.

3. Legends of Horror

Are you ready for spooky season? Casa Loma’s terrifying Legends of Horror returns on Oct 4. Wander through 2 km of spine-chilling sets, live actors, and special effects that bring classic horror legends to life.

Where: Casa Loma (1 Austin Terrace, Toronto, ON M5R 1X8)

When: October 4th to November 1st, 2025

Price: Starting at $52.34

Category: Date/Friends

Click here for the website.

4. Canada’s Wonderland: The Conjuring: Beyond Fear

Visit Canada’s Wonderland this fall for their new experience: The Conjuring: Beyond Fear. Navigate iconic scenes and run into infamous entities like The Nun, The Crooked Man, and Annabelle! 

Where: Canada’s Wonderland (1 Canada's Wonderland Drive, Vaughan, ON L6A 1S6)

When: September 26th to November 1st, 2025 

Price: Starting at $45

Category: Date/Friends

Click here for the website.

5. Bryan Adams - Roll with the Punches Tour

Canada's Walk of Fame inductee Bryan Adams will perform live at Scotiabank Arena this month with special guests The Sheepdogs.

Where: Scotiabank Arena (40 Bay St., Toronto, ON M5J 3A5)

When: October 3rd, 2025 (7:30 pm - 10:30 pm)

Price: Starting at $200

Category: Date/Friends

Click here for the website.

6. PumpkinFest Toronto

Enjoy a weekend filled with unlimited midway rides, unlimited inflatable fun, a sprawling pumpkin patch, local food trucks, live entertainment, tons of family photo ops, and so much more!

Where: Downsview Park (35 Carl Hall Road, Toronto, ON M3K 2B6)

When: October 10th to 13th, 2025 (10 am - 6 pm)

Price: Starting at $15

Category: Family-friendly

Click here for the website.

7. Adam Sandler - You’re My Best Friend Tour

From the big screen to the stage, comedy superstar Adam Sandler is on tour and heading to Toronto. Expect laugh-out-loud stories, music, and the offbeat humor that’s made him a household name for decades.

Where: Scotiabank Arena (40 Bay St., Toronto, ON M5J 3A5)

When: October 12th, 2025 (7:30 pm)

Price: Starting at $260

Category: Date/Friends

Click here for the website.

8. Elevate Festival 2025

Elevate Festival returns to Toronto to reunite world-class innovators, industry leaders, and the tech ecosystem to shine a global spotlight on Canada’s tech and innovation ecosystem.

Where: Multiple locations

When: October 7th to 9th, 2025

Price: Starting at $325

Category: Networking

Click here for the website.

9. Ice Cube - Truth to Power: Four Decades of Attitude

Hip-hop legend Ice Cube is bringing his iconic sound to Toronto this year. Get ready for an electrifying night filled with classic hits, unstoppable energy, and the kind of stage presence only Cube can deliver.

Where: Scotiabank Arena (40 Bay St., Toronto, ON M5J 3A5)

When: October 9th, 2025 (8 pm)

Price: Starting at $80

Category: Date/Friends

Click here for the website.

10. Fall for Dance North Festival

Toronto’s beloved Fall for Dance North Festival returns this fall, celebrating movement in every form. With world-class performers, bold choreography, and accessible ticket pricing, it’s one of the city’s most inspiring cultural events of the season.

Where: Multiple locations

When: October 15th to 26th, 2025

Price: $25

Category: Date/Friends

Click here for the website.

11. Toronto Cocktail Festival

Toronto Cocktail Festival is a toast to the art of the cocktail and so much more. It’s a destination event that celebrates the vibrant culture of food and drink in a city that is a hub of culinary and cocktail creativity

Where: Multiple locations

When: October 22nd to 26th, 2025

Price: Prices vary

Category: Date/Friends

Click here for the website.

12. Art Toronto 2025

Art Toronto is back for 2025, transforming the Metro Toronto Convention Centre into a hub of creativity. Canada’s leading international art fair showcases galleries, installations, and artists from around the globe — a must-visit for collectors and culture lovers alike.

Where: Metro Toronto Convention Centre North Building (255 Front St W, Toronto, ON M5V 2W6)

When: October 23rd to 26th, 2025

Price: Starting at $30

Category: Date/Friends

Click here for the website.

13. All Things Go Music Festival

All Things Go Music Festival is coming to Toronto for the first time ever! Get ready to see amazing artists live including Reneé Rapp, Kacey Musgraves, and Noah Cyrus.

Where: Budweiser Stage (909 Lake Shore Blvd W, Toronto, ON M6K 3L3)

When: October 4th and 5th, 2025

Price: Starting in the $200s

Category: Date/Friends

Click here for the website.

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