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Enjoy the last full week of September in Toronto! This week brings lots of amazing sports games, including the return of the Toronto Maple Leafs. There are also great concerts, festivals, and even a banana-themed bar crawl.
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1. Water/Fall Festival
The first-ever Water/Fall Festival is coming to Toronto’s waterfront for two weekends with a free celebration featuring public art installations, harvest-themed food and drink, live music, dance performances, a sustainable makers market, illuminated boat tours, and more. Plus, 100+ colourfully choreographed canoes will be paddling across the eastern waterfront in ‘A Lake Story’, so 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 28th-28th & October 4th-5th, 2025
Price: Free admission
Category: Family-friendly
2. Gemlet Sherway Gardens
Celebrate your milestones in style at Gemlet Sherway Gardens! Book a party appointment with 4 or more friends to enjoy 20% off your permanent jewelry. Sip on complimentary refreshments while you create lasting memories with matching, water-resistant pieces. Show this post upon arrival to receive this offer.
Where: Sherway Gardens (25 The West Mall, Toronto, ON M9C 1B8)
When: September 24th-October 8th, 2025
Price: Prices start at $6/inch
Category: Family-friendly
3. Toronto Blue Jays Fan Appreciation Weekend
The Blue Jays last homestand weekend of the regular season is dedicated to their devoted fans! Throughout the ballpark there will be a variety of fun games and activities for fans of all ages. There will also be chances to win premium prizes!
Where: Rogers Centre (1 Blue Jays Way, Toronto, ON M5V 1J3)
When: September 26th to 28th, 2025
Price: Starting at $46
Category: Family-friendly
4. ROM Tuesday Night Free
Did you know that the Museum is free for everyone this Tuesday? Tickets are released 2 weeks prior to the event, and walk-ins are not available. Don’t miss this opportunity to see amazing exhibits for free!
Where: 100 Queen’s Park, Toronto, ON M5S 2C6
When: September 23rd, 2025
Price: Free
Category: Family-friendly
5. Toronto Maple Leafs Preseason
Hockey is back! The Leafs return to the ice for their preseason matchups, giving fans a first look at what’s to come this year.
Where: Scotiabank Arena (40 Bay St., Toronto, ON M5J 3A5)
When: September 23rd and 27th, 2025
Price: Starting at $75
Category: Family-friendly
6. The Word On The Street's 36th Annual Festival
Toronto’s beloved literary festival returns to celebrate books, writers, and readers with panels, signings, and plenty of inspiration.
Where: David Pecaut Square (215 King St W, Toronto, ON M5V 3G2)
When: September 27th to 28th, 2025
Price: Free
Category: Family-friendly
7. Just For Laughs Toronto
Enjoy the final week of Just For Laughs Toronto! Get ready for nonstop comedy featuring some of the best in the game! From comedy legends to viral sensations, local favourites to international stars, this isn’t something that you’ll want to miss.
Where: Multiple locations
When: September 18th to 27th, 2025
Price: Prices vary
Category: Date/Friends
8. Lorde - Ultrasound Tour
New Zealand singer, Lorde, is coming to Toronto with her fourth concert tour this week. Enjoy favourite songs like Royals and Supercut.
Where: Scotiabank Arena (40 Bay St., Toronto, ON M5J 3A5)
When: September 24th, 2025 (7 pm)
Price: Starting at $180
Category: Date/Friends
9. AGO Art Bash 2025
Celebrate 125 years of the AGO at Canada's ultimate art party! Explore galleries that have inspired generations of artists, discover exciting contemporary takes on iconic works, sip on cocktails, savour delicious bites, and raise a glass to another 125 years of art, culture, and community.
Where: 317 Dundas Street West, Toronto, ON M5T 1G4
When: September 25th, 2025 (8 pm)
Price: $250/person
Category: 19+
10. Lainey Wilson - 2025 Whirlwind World Tour
Calling all country fans! Lainey Wilson is coming to Budweiser Stage this week. So grab your watermelon moonshine and get ready for an amazing night of music.
Where: Budweiser Stage (909 Lake Shore Blvd W, Toronto, ON M6K 3L3)
When: September 25th, 2025 (7 pm)
Price: Starting in the $100s
Category: Date/Friends
11. 2025 Fall Home Show
Check out the Fall Home Show for all things home related! Where else can you find over 225 home and lifestyle vendors, plan your next renovation, and learn from the experts, all in one place?
Where: Enercare Centre, Exhibition Place (100 Princes' Blvd, Toronto, ON M6K 3C3)
When: September 26th to 28th, 2025
Price: $15
Category: Date/Friends
12. Banana Bar Crawl
The Banana Bar Crawl is back in Toronto and it’s bigger, better, and more bananas than ever! Your ticket includes entry to all participating bars, a banana costume, exclusive drink specials, and more.
Where: Multiple locations
When: September 26th, 2025
Price: Starting at $20
Category: 19+
Community Events
1. Wardruna: World Tour 2025 - Part ll
Norwegian music collective Wardruna brings their haunting, Nordic-inspired sound to Massey Hall on September 22 at 7:30 PM. Joined by special guest Chelsea Wolfe, this immersive live experience blends ancient traditions with modern atmospheric music.
Where: Massey Hall (178 Victoria St)
When: September 22nd, 2025 (7:30 PM – 10:30 PM)
Click here for more information.
2. MLB: Toronto Blue Jays vs. Boston Red Sox
Catch the Toronto Blue Jays as they take on the Boston Red Sox in an exciting matchup. Don’t miss the chance to cheer on the home team and experience the energy of live baseball.
Where: Rogers Centre (1 Blue Jays Way, Toronto, ON M5V 1J3)
When: September 23rd-25th, 2025 (7:07 PM – 9:30 PM)
Click here for more information.
3. MLB: Toronto Blue Jays vs. Tampa Bay Rays
Watch the Toronto Blue Jays take on the Tampa Bay Rays in an action-packed game. Come cheer on the home team and experience the excitement of live baseball.
Where: Rogers Centre (1 Blue Jays Way, Toronto, ON M5V 1J3)
When: September 26th-28th, 2025
Click here for more information.
4. The Walrus Talks The Power of Animals
At The Walrus Talks The Power of Animals, seven expert speakers will discuss how a sustainable future is shaped by how we treat animals. How does better overall farm animal treatment protect humans from the development of antimicrobial resistance? What are the economic advantages of advancing animal welfare? And how can sustainable farming practices serve as an essential strategy for environmental conservation, promoting ecological balance, and protecting animal habitats? Whether you're passionate about animal welfare, curious about ethical food choices, or interested in conservation efforts, this event will spark meaningful conversations and inspire action.
Where: Isabel Bader Theatre (93 Charles Street West Toronto, ON M5S 2C7)
When: September 23rd, 2025 (7:00 PM)
Click here for more information.
5. CookUnity Pop-Up
Passersbys can enjoy a memorable meal (to go!) created by award-winning chefs, including Patrick Kriss (Alo), Trevor Lui (Highbell Hospitality Group), Hemant Bhagwani (Bar Goa), and Dadrian Coke (Chubby’s Jamaican Kitchen). While supplies last.
Where: Bay-Adelaide Centre Courtyard (40 Temperance St, Toronto, ON M5H 0B4)
When: September 23rd-24th, 2025 (7:00 PM)
Click here for more information.
6. Toronto Maple vs Ottawa Senators
The Toronto Maple Leafs go head-to-head with the Ottawa Senators in a battle of Ontario! Get ready for a rivalry game full of energy and excitement!
Where: Scotiabank Arena, Toronto
When: September 23rd, 2025 (12:00 PM-2:00 PM)
Click here for more information.
7. Fifth Element at Reid’s Distillery
On Wednesday, September 24th, Fifth Element will return to Reid's Distillery for more gin and jazz. Enjoy beautiful arrangements of music from the Great American Songbook and more. Join for cocktails, snacks and lovely music in a relaxed and comfortable setting.
Where: Reid’s Distillery (32 Logan Avenue)
When: September 24th, 2025 (8:00 PM-10:00 PM)
Click here for more information.
8. Paulaner's Oktoberfest Party at Waterworks
Toronto, it’s time to raise a stein! Waterworks Food Hall is turning into a Bavarian-style beer hall as Germany's #1 Oktoberfest Beer, Paulaner, takes over for the ultimate Oktoberfest party. Whether you’re rocking lederhosen or just here for the lager, this is your chance to sip, snack, and celebrate Oktoberfest in style.
Where: Waterworks Food Hall (17 Maud St, Toronto, ON M5V 2M5)
When: September 27th, 2025 (Starts at 9:00 PM)
Click here for more information.
9. Canadian Opera Company Open House
Visitors will be invited to go behind the scenes on guided tours, explore costumes, props, and history, and enjoy sneak-peek performances from this season’s productions, including Romeo et Juliette. Interactive activities, prizes, and refreshments will be available on site.
Where: Four Seasons Centre for the Performing Arts (145 Queen St W)
When: September 27th, 2025 (1:00 PM - 3:00 PM)
Click here for more information.
10. Deeper Connections: Make New Friends for Women: Toronto City Walk Edition
Explore Toronto, meet like-minded women & make new friends through fun icebreakers, speed friending & city walks. Connection made easy!
Where: Berczy Park Dog Fountain (35 Wellington Street East Toronto, ON M5E 1C6)
When: September 27th, 2025 (12:30 PM - 3:00 PM)
Click here for more information.
11. Toronto City Walk: Speed Dating Edition ( ages 30+)
Speed-date while doing fun activities in the streets of Toronto.
Where: Berczy Park Dog Fountain (35 Wellington Street East Toronto, ON M5E 1C6)
When: September 27th, 2025 (4:30 PM - 7:00 PM)
Click here for more information.
12. Toronto Maple vs Montréal Canadiens
The Toronto Maple Leafs take on the Montréal Canadiens in a legendary matchup that never disappoints. A rivalry fueled by history—who will claim the win this time?
Where: Scotiabank Arena, Toronto
When: September 27th, 2025 (7:00 PM)
Click here for more information.
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