Photo Credit: Rizaldy Scott Flickr
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Enjoy another great weekend in Toronto! There are so many fun things to do so keep reading to find out more.
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1. American Tall Pop-Up
The first-ever American Tall pop-up store is taking place this week! Made for tall and designed exclusively for men 6’0” to 7’1” and women 5’9” to 6’6”, this 3-day event offers in-person shopping for all the best sellers and new fall styles, surprise giveaways, and a special bonus for early birds where the first 50 attendees on each day can customize select pieces with exclusive patchwork touches.
Where: SPACE on KING (300 King St E, Toronto, ON M5A 1K4)
When: September 19th-21st, 2025
Price: Free admission
Category: Family-friendly
2. Just For Laughs Toronto
Get ready for 10 days of nonstop comedy featuring some of the best in the game! From comedy legends to viral sensations, local favourites to international stars, September's shaping up to be the best month of the year.
Where: Multiple locations
When: September 18th to 27th, 2025
Price: Prices vary
Category: Date/Friends
3. VegTO
Canada's largest free-to-attend vegan festival is back! It’s a celebration of all things plant-based. Expect delicious food, local vendors, and inspiring talks.
Where: Nathan Phillips Square (100 Queen St W, Toronto, ON M5H 2N3)
When: September 20th and 21st, 2025
Price: Free entry
Category: Family-friendly
4. Toronto Vintage Show
Calling all vintage lovers! This is Canada’s largest sale of vintage clothing and vintage decor. Explore vintage clothing from the 1950’s all the way to Y2K.
Where: Queen Elizabeth Building at Exhibition Place (180 Princes’ Blvd, Toronto, ON M6K 3C3)
When: September 20th and 21st, 2025
Price: $15
Category: Date/Friends
5. Thai Festival
This festival will be an incredible celebration of Thai food and culture! Enjoy 40+ food vendors, local Thai-owned businesses, dancing, music, live entertainment, and more.
Where: Sankofa Square (1 Dundas St E, Toronto, ON M5B 2R8)
When: September 20th and 21st, 2025
Price: Free admission
Category: Date/Friends
6. TSO Open House & Free Concert
Discover the thrill of the symphony at the TSO Open House & Free Concert! Enjoy interactive fun, test-drive instruments, experience live performances, and more. Admission is free but tickets are required.
Where: Roy Thomson Hall (60 Simcoe St, Toronto, ON M5J 2H5)
When: September 20th, 2025
Price: Free (tickets required)
Category: Family-friendly
7. The Queen West Art Crawl
This annual outdoor art exhibition will feature over 100 of Canada's most innovative established and emerging artists. There will also be music, dance, a kid zone, and more!
Where: Trinity Bellwoods Park (790 Queen St W, Toronto, ON M6J 1G3)
When: September 20th to 21st, 2025
Price: Free admission
Category: Family-friendly
8. Water Lantern Festival
Witness the beauty of thousands of lanterns and the lights reflecting upon the water on an emotional and unforgettable night. You’ll get to decorate your own lantern and release it onto the water. Enjoy food trucks, live music, vendors, a scavenger hunt, and the lantern launch.
Where: Downsview Park (70 Canuck Ave, North York, ON M3K 2C5)
When: September 19th to 20th, 2025
Price: $47.99/person
Category: Family-friendly
9. All Elite Wrestling: All Out
Calling all wrestling fans! For the first time ever, All Elite Wrestling brings to you one of the biggest PPV events of the year as AEW All Out invades the Scotiabank Arena.
Where: Scotiabank Arena (40 Bay St., Toronto, ON M5J 3A5)
When: September 20th, 2025 (1:45 pm)
Price: Starting at $70
Category: Date/Friends
10. PIN & PATCH SHOW 2025
The PIN & PATCH SHOW is back! This event will feature dozens of talented pin and patch artists from Toronto and across Canada.
Where: The Parkdale Hall (1605 Queen St W #2, Toronto, ON M6K 3B8)
When: September 20th, 2025 (10 am - 5 pm)
Price: Free entry
Category: Family-friendly
11. The Sunrise Social
The Sunrise Social is a morning festival of activities designed to supercharge your mind and body in the ultimate wellness circuit. Your ticket gives you access to one breath & movement session, and unlimited access to the saunas and cold plunges for the duration of the event.
Where: The Bentway (250 Fort York Boulevard Toronto, ON M5V 3K9)
When: September 20th, 2025 (9 am - 1 pm)
Price: $67.99
Category: Friends
12. Brunch Club Art Making Workshop
This is a relaxed and social art class designed to combine creativity with brunch! Enjoy coffee and pastries followed by an art workshop. The event ends with a Prix Fixe Brunch Menu. Gallery admission, sketching supplies and brunch are included in the fee.
Where: AGO (317 Dundas Street West, Toronto, ON M5T 1G4)
When: September 20th, 2025 (11:30 am - 2:30 pm)
Price: $140
Category: Date/Friends
13. Twenty One Pilots: The Clancy Tour
Twenty One Pilots is coming to Budweiser Stage this weekend. Don't miss this chance to hear classic songs like Stressed Out and Ride, as well as their new album that was just released.
Where: Budweiser Stage (909 Lake Shore Blvd W, Toronto, ON M6K 3L3)
When: September 20th and 21st, 2025 (8 pm)
Price: Starting at $90
Category: Date/Friends
Community Events
1. Sarah Millican: Late Bloomer Tour
After a sold-out show in 2022, the hilarious Sarah Millican returns to Toronto with her brand-new stand-up show, Late Bloomer. Don’t miss an evening of sharp wit and laugh-out-loud comedy from one of the UK’s top comedians.
Where: Meridian Hall (1 Front St E, Toronto, ON M5E 1B2)
When: September 19th-21st, 2025 (7:00 PM – 9:00 PM)
Click here for more information.
2. Viagra Boys - The Infinite Anxiety Tour of 2025
Swedish post-punk band Viagra Boys bring their high-energy, genre-bending sound to History Toronto on September 20 at 7:00 PM as part of The Infinite Anxiety Tour 2025. Don’t miss this electrifying live performance.
Where: History (1663 Queen St E, Toronto, ON M4L 1G5)
When: September 20th, 2025 (7:00 PM)
Click here for more information.
3. SYML - Nobody Lives Here Tour
Indie singer-songwriter SYML brings his heartfelt melodies and atmospheric sound to The Danforth Music Hall on September 20 at 7:00 PM as part of the Nobody Lives Here Tour. Don't miss this intimate and moving live performance.
Where: The Danforth Music Hall (147 Danforth Ave, Toronto, ON M4K 1N2)
When: September 20th, 2025 (7:00 PM)
Click here for more information.
4. Sunday SerVice: Starting From Scratch | Manzone & Strong
Put on your Sunday best, sip your tips, or ride that bender. Join us for a late check-out and reset your week at Wiggle Room at the Industry Weekly Social.
Where: Wiggle Room (772 Dundas St W, Toronto, ON)
When: September 21st, 2025
Click here for more information.
5. The Ottawa Guitar Trio
Presenting a program of guitar trio arrangements of music movie themes/ video game themes and. Classical standards all arranged by this ensemble.
Where: St Andrews Church 73 Simcoe street, Toronto.
When: September 20th, 2025
Click here for more information.
6. Miz Megs [Bday Beats] | Manzone & Strong | Flipside
Manzone & Strong | Flipside | Loopity Scott | missKriss + special art installation by Soap Bubble Studio [bday beats] #WiggleRoomToronto is the #HomeofBouncyBeats
Where: Wiggle Room (772 Dundas St W)
When: September 20th, 2025
Click here for more information.
7. 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 20th, 2025 at 12:00 PM
Click here for more information.
8. Messy's Drag Bingo Brunch @ Sneaky Dee's
Join for an unforgettable afternoon of fabulous entertainment at Messy's Drag Bingo Brunch @Sneaky Dee's! Get ready for a fun afternoon with Toronto's delusional Diva Messy Margaret while enjoying some delicious brunch items and playing a four rounds of bingo! They have prizes sponsored by LOVESHOP and MORE!
Where: Sneaky Dee's (431 College Street Toronto, ON M5T 1T1)
When: September 21st, 2025 at 12:00 PM
Click here for more information.
9. Dreamscapes by Endy Petit
Step into Dreamscapes, by Endy Petit, an immersive, whimsical world inspired by the power of sleep. Designed for young families and kids-at-heart, Dreamscapes invites you to experience how Endy’s new Petit collection of mattresses, bedding and playful furniture, makes sleep better so kids can shine brighter.
Where: Wychwood Barns, 601 Christie St., Toronto
When: September 20, 2025 (9:00 AM – 4:00 PM)
Click here for more information.
10. The Way Back at The Duke Toronto
The Way Back is pumped to return to The Duke Toronto on Saturday, September 20th from 8:00 to 11:00 pm. Join for an evening of pop covers from the 60s to 90s, delivered by Brian Fukuzawa (guitar and vocals), Brian Hargan (vocals, tambourine and cowbell), Peter Neumann (bass and vocals), Tom Melville (piano), Andrew Werbowski (drums) and Nina Richmond (vocals).
Where: The Duke Toronto (1225 Queen Street East)
When: September 20, 2025 (8:00 PM – 11:00 PM)
No link. Reserve your table by calling 416-466-2624.
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