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Can you believe that it’s the final weekend in September? Enjoy amazing events like Shawn Mendes’ concert, a festival dedicated to garlic, and lots of exciting sports games.
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1. Shawn Mendes - On The Road Again
Toronto local, Shawn Mendes, is back this weekend to perform his new album, Shawn. This is sure to be an amazing show at Budweiser!
Where: Budweiser Stage (909 Lake Shore Blvd W, Toronto, ON M6K 3L3)
When: September 28th, 2025
Price: Starting at $155
Category: Date/Friends
2. Toronto Garlic Festival
This unique festival returns to Toronto for its 14th year. Visitors can stock up on their winter supply of Ontario-grown garlic, enjoy delicious food, watch a vampire costume contest, and so much more!
Where: Spadina Road from Davenport to Dupont
When: September 28th, 2025 (10 am to 5 pm)
Price: Free admission
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. 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 27th, 2025
Price: Starting at $75
Category: Family-friendly
5. Toronto FC vs Inter Miami CF
Calling all soccer fans! Toronto FC faces off against Inter Miami CF this weekend which brings legendary athlete Lionel Messi to the city.
Where: BMO Field (170 Princes' Blvd, Toronto, ON M6K 3C3)
When: September 27th, 2025 (4:30 pm)
Price: Starting in the $200s
Category: Date/Friends
6. The Toronto Halloween Show
Are you excited for Halloween? This weekend, one of Ontario’s largest consumer shows for all things Halloween comes to Toronto. Shop everything from decor to costumes and makeup and everything in between.
Where: Exhibition Place (100 Princes Blvd, Toronto, Ontario, M6K 3C3)
When: September 27th and 28th, 2025
Price: Starting at $13
Category: Date/Friends
7. 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
8. Fall Harvest Market 2025
Check out Toronto’s brand-new Fall Harvest Market, right on the waterfront! Discover fresh produce, delicious treats, artisanal goods, unique finds, and more, from over 40 vendors.
Where: HTO Park (339 Queens Quay W, Toronto, ON M5V 1A2)
When: September 27th and 28th, 2025
Price: Free entry
Category: Family-friendly
9. Gatsby Redux
Step into the world of Gatsby at this immersive outdoor performance. You’ll be transported to the glamorous world of the Roaring Twenties as you enjoy an incredible theatrical experience.
Where: 235 Queens Quay W, Toronto, ON M5J 2G8
When: September 27th and 28th, 2025 (6 pm - 7:30 pm)
Price: $65
Category: Date/Friends
10. 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
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
Community Events
1. 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.
2. Murdoch Mysteries Escape Room
Step into the world of Murdoch Mysteries and become a constable on the case. Detective Murdoch is missing, and it's up to you and your team to track him down by hunting for clues and solving puzzles before time runs out. Follow in his footsteps at Station House No. 4 and match wits with the notorious serial killer Harlan Hobbes in this immersive escape room adventure.
Where: Casa Loma (1 Austin Terrace, Toronto, ON M5R 1X8)
When: Until September 30, 2025
Click here for more information.
3. Femme Fatale Comedy Show
Check out Canada’s only weekly female comedy showcase at Femme Fatale Comedy, Toronto’s premier stand-up show featuring the city’s funniest and most fearless female comedians. This isn’t just any comedy night—it’s a celebration of bold, brilliant women redefining stand-up on their own terms.
Where: The Comedy Lab (298 Brunswick Ave, Toronto, ON M5S 2M7)
When: September 27, 2025
Click here for more information.
4. Messy's Drag Bingo Brunch @ Super Bargain
Messy’s Drag Bingo at Super Bargain is back with a brunch twist, featuring a buffet, four rounds of bingo with prizes, and high-energy lip sync performances from Messy Margaret for a lively and unforgettable experience.
Where: Super Bargain (441 Parliament Street Toronto, ON M5A 3A1)
When: September 27th, 2025 at 12:00 PM
Click here for more information.
5. Drag Brunch @Church Street Garage
Join their rotating hosts Messy Margaret, Sanjina (Canada’s Drag Race Season 5), Madee Lovegood, and special guests for a wild and unforgettable Drag Brunch experience! Expect high-energy performances, laughs, and the best brunch vibes in the city.
Where: Church St. Garage Bar (477 Church Street Toronto, ON M4Y 2C6)
When: September 27th, 2025 at 12:00 PM
Click here for more information.
6. Fashion Brunch 2025
Fraternity Brand and Sundé Social present The Fashion Brunch — a showcase of homegrown designers’ fall/winter lines, live music, art, brunch bites, vendors, and networking, all in one vibrant venue.
Where: Avant Garde Gallery (218 Merton Street Toronto, ON M4S 1A1)
When: September 28th, 2025
Click here for more information.
7. 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.
8. 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.
9. 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.
10. 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.
11. Brunch, Paint & Connect
Brunch, Paint and Connect is a unique event combining a paint night, brunch, and networking. Enjoy great food, new connections, and a fun painting lesson on the covered rooftop patio at The Pilot in Yorkville.
Where: 22 Cumberland St, Toronto, ON M4W 1J5
When: September 28th, 2025 (12:00 PM - 3:00 PM)
Click here for more information.
12. Not Another Day Party
End the season at Not Another Day Party, where Dancehall, Soca, Afrobeats, and Amapiano collide for the ultimate music experience.
Where: Rebel Noir (11 Polson St)
When: September 27th, 2025 (3:00 PM - 10:00 PM)
Click here for more information.
13. 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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