Toronto Festivals & Events for Next Week (Sept 22 - Sept 28)

September 20, 2025 • Estimated Reading Time: 24 minutes

Toronto Festivals & Events for Next Week (Sept 22 - Sept 28)

Hey Torontonians, 🎭 What The Festival is Back This September!

Looking for something new and unexpected this fall? Toronto’s most weird, wild and wonderful festival is back.

📅 September 25-27, 2025
📍 Youngplace 180 Shaw Street
💸 Tickets: $15-$35

What The Festival is a live entertainment event celebrating vibrant performances of Drag, Clown, and Puppetry. We’re back this fall with a wide range of wonderful shows, wild cabarets, a hands-on workshop, and more! Suitable for audiences 18+.

✨ Perfect for:

  • Friends looking for a unique night out

  • Art lovers ready to explore bold new ideas

  • Anyone who enjoys asking “what just happened?” (in the best way)

🎟️ Get Tickets Here
More details on the full lineup: wtfestival.ca/now
Don’t just hear about it later. Be part of it.

Anyway, checkout what you can do this Friday (9/22) to Sunday (9/28) below! Hope you have a great weekend❣️ Missed out? Catch up with our previous newsletter here.

Monday 09/22

🎵 Music
Ryder the Eagle with Fox Atticus @ The Baby G
Venus Fest @ Allan Gardens
Wardruna: World Tour 2025 - Part ll @ Massey Hall

🎡 Family
Harry Potter Movie Trivia @ The Pilot

Tuesday 09/23

🍽️ Food and Drinks
CookUnity Fall Pop-Up: Free Chef-Crafted Meals @ Bay-Adelaide Centre Courtyard - 40 Temperance St, Toronto, ON M5H 0B4 (Free)
Moon & Pepper @ Curryish Tavern (Free)

🎵 Music
Open Mic at The Wych @ Davenport & Ossington, Toronto
Ray LaMontagne - Trouble 20th Anniversary Tour @ Massey Hall
Sunday 1994 - The Prairie Tour @ The Mod Club (formerly known as The Axis Club)

🎉 Entertainment
BST Vacations Fall Travel Showcase, Toronto @ Royal Canadian Legion Branch 101 (Free)
Colonial Circus @ Aki Studio
Gilmore Girls Trivia Night - Snakes & Lattes College @ Snakes and Lattes College St.
Sabrina Wu - JUST FOR LAUGHS TORONTO @ Comedy Bar East
The Valley Trivia @ Hemingway's

🏒 Sports
MLB: Toronto Blue Jays vs. Boston Red Sox @ Rogers Centre

🎡 Family
Charm Bracelet Workshop @ Old Flame Brewery
Kimberlite Enterprises Woman to Woman event @ HamsArt Market Souk Café
Let's Make Toronto More Bird-Friendly @ Palmerston Library

📅 Other Events
The Reading Sanctuary Book Club @ Common Ground Therapy

Wednesday 09/24

🍽️ Food and Drinks
Paris with a twist - Patio edition @ King West
Sicilian Night at Biagio Ristorante @ Biagio Ristorante
Treat O'Clock @ Multiple Venues (Free)

🏒 Sports
MLB: Toronto Blue Jays vs. Boston Red Sox @ Rogers Centre

🎭 Art and Culture
Beyond the Land: A Book Club in Honour of the Truth and Reconciliation Day @ Nuttea Toronto
Brian Stewart On the Ground @ St. Andrew's Church
Hand Printed Tote Bags with Flycatcher Press @ Gwartzman's Art Supplies
Mara Eagle in Conversation @ Art Gallery of Ontario (Free)
Public Enemy @ Alumnae Theatre
Shab-e She'r Poetry Night XCIV @ Living Room, Tranzac Club
Upcycled Weaving at Gallery 1065 @ Gallery 1065

📅 Other Events
Marketing After-Hours TO @ BrainStation

Thursday 09/25

🎵 Music
Babytron at The Phoenix - Sept 25 @ Phoenix Concert Theatre
Ducks LTD & The Tubs @ Lee's Palace
Enoch Turner on Tap @ Enoch Turner Schoolhouse
Lael Neale & Isla Craig & Guy Blakeslee: Wavelength @ Wavelength @ St. Anne's
Lainey Wilson - 2025 Whirlwind World Tour @ Budweiser Stage
Le Cabaret Bleu 2 @ The Painted Lady, Toronto
QUAL @ The Garrison
Tune In Thursdays: Sound Bath & Vocal Toning Workshops @ Grateful Den

🎭 Art and Culture
AGO Art Bash 2025 @ Art Gallery of Ontario
Collage Night @ Typist Studios & Coffee
Gladstone House Unveils New Exhibitions @ Gladstone House
icehouse & friends presents: Qurat Dar, Shane Nielson, and Shannon Arntfield @ Flying Books
On The Edge: Photographs of Toronto's downtown waterfront 2023-2025 by Steven Evans @ Paul H. Cocker Gallery, Department of Architectural Science, Toronto Metropolitan University
Paint & Sip - Paint Night - End of Summer Glow Acrylic Painting @ Fresh Paint Studio Danforth East
TORONTO TANGO 8 FESTIVAL & MARATHON @ Argentine Tango Toronto by Bulent & Lina
Trivia Paint Night @ Artbox
What The Festival @ Youngplace

🎡 Family
Board Game Designer Night at The Black Pony in East End Toronto @ Black Pony
University College Book Sale @ University College, University of Toronto

📅 Other Events
Career Carnival 2025 @ Jamaican Canadian Association

Friday 09/26

🎵 Music
Basement Mixtapes - 90's Afterdark @ The Wych (Free)
CHRIS CAMPOS [bday beats] @ Wiggle Room (Free)
Dance Night @ 783 College Street
Dirt Dragon LIVE Y2K Cover Band @ Annex Social
DJ SLANDER - Voyager Tour @ Budweiser Stage
Julia D'Angelo Live at The Painted Lady @ The Painted Lady
Mozart 40 & Schubert 5, Presented by Tafelmusik @ Koerner Hall
Persian Psychodelia night @ Meridian Arts Centre
SOLD OUT - Totally 2000's Video Dance Party, Totally FREE with DJ Starting From ScratchZ103.5 & The Phoenix Concert Theatre presents\nSOLD OUT \u2013 Totally 2000\u2019s Video Dance Party, Totally FREE w/ DJ Starting From Scratch\n19+\nSOLD OUT ~ For a chance to Win to Get In listen to Z103.5\nFri Sept 26th, Doors at 9pm, 19+ ID required\nTotally 2000s. Totall...Phoenix Concert Theatre @ Phoenix Concert Theatre (Free)
TAXI GIRLS/SUNNY DEE & THE FLOWER PEDALS/SECOND WIFETAXI GIRLS/SUNNY DEE & THE FLOWER PEDALS/SECOND WIFE\nSEPT 26TH @ NO NO ROOM * DOCK ELLIS\n15$ ADV,20$ DOORS\n8PM,19+The Dock Ellis @ The Dock Ellis
The Hogtown Allstars @ Old Mill Toronto
TRANCE TRIP @ SEE-SCAPE, Toronto
VPS x Libertine @ The Libertine, Toronto
Wax Candy Friday Night Disco!Special 7\ guest set by French For Horse!" @ The Piston

🎉 Entertainment
Antonio De Vitto@ Backroom Comedy Club - Limited Run @ Backroom Comedy Club
Banana Bar Crawl @ Multiple Venues
Board Game Night at Left Field Brewery in Liberty Village Toronto @ Left Field Brewery Liberty Village
Canada's Wonderland Halloween Haunt 2025 @ Canada's Wonderland
Gavin Matts - JUST FOR LAUGHS TORONTO @ The Randolph Theatre
Gay AF @ Just For Laughs Toronto @ Comedy Bar
GOOD FRIDAY TRIVIA NIGHT @ GRETA @ Greta Bar Toronto
Ian Fidance - JUST FOR LAUGHS TORONTO @ Comedy Bar East
Midtown Toronto Comedy Showcase - Free admission! @ Dopamine Lounge (Free)
Silent Dance Party in St. James ParkKick off your weekend with a dance party like no other! On Friday ,September 26th, 7-10pm, St. James Park transforms into an open-air dance floor where you control the music. Put on the provided wireless headphones (included with your ticket) and choose betwee...St James Park @ St James Park
The Bulwark Live @ The Royal Theatre
The Liberty Laughs Comedy Show - Friday September 26, 2025 @ Liberty Village Market & Cafe, Toronto

🏒 Sports
MLB: Toronto Blue Jays vs. Tampa Bay Rays @ Rogers Centre

🎭 Art and Culture
A Better Tomorrow @ Fox Theatre
A Fairytale for Joyce @ Art Gallery of Ontario
Glow-in-the-Dark Paint Night @ Artbox
Paint & Sip Workshop - Silk Scarf Painting Workshop @ Fresh Paint Studio Danforth East
Peace Ambassadors Awards Gala & Grand Ball @ Omni King Edward Hotel
Riverdale Art Show and Sale35th Anniversary with 22 talented artists all from the Toronto area @ St Barnabas Anglican Church
Sippin Socials Paint Night For Plexiglass PortraitsJoin us for an unforgettable evening at Sippin\u2019 Socials - Plexiglass Portraits with celebrated artist Tanzina Amin. This fun, relaxed paint night blends creativity, great conversation, and a perfectly paired drink. Beer is included in the price of admission!\nY...Neilson Park Creative Centre @ Neilson Park Creative Centre
Through the Lens of Ukrainian Belonging @ Shevchenko Museum, Toronto
Toronto: Canadian Modern & Beyond @ Multiple Venues, Toronto

🎡 Family
2025 Fall Home Show @ Enercare Centre, Exhibition Place
PA Day Family Movie - Butterfly Tale @ Palmerston Library
The Holistic Market Toronto @ Christie Pits Park

Saturday 09/27

🍽️ Food and Drinks
Fall Harvest Market 2025 @ HTO Park
GLB Oktoberfest @ Great Lakes Brewery
Oktoberfest @ JCS Banquet Hall
Oktoberfest at Rorschach @ Rorschach Brewing
Tunisian Tea Party by Fatima Khlifi @ The Depanneur

🎵 Music
1 special night with the Brothers of House groupSat Sep 27: Junior Lopez & Corrado Q | GMOney | 3ROC | SoulSista | Tomy Villacorta & Adriano Longi @ Wiggle Room
9th Annual KISS CF Goodbye Concert Fundraiser for Cystic Fibrosis Sept. 27 @ The Opera House
9th Annual KISS CF Goodbye Sept 27 2025 @ Opera House
80s/90s Video Dance Party w/ BOWIE Spotlight - PANIC - 2 Year Anniversary of Ground ControlLiving On Video + DJ Lazarus presents @ Ground Control
AIDONIA, MASICKA, MALIE DON LIVE in Concert @ Fort York
Charity Concert for Indigenous Affordable Housing @ Hugh's Room
Collide-o-Scope @ Tranzac Club
ENCHANTMENT-The Art Of Songwriting with Lily Frost @ Community Outwitch
Jazz and Love @ Super Wonder Gallery
Maruja at The Phoenix - Sept 27 @ Phoenix Concert Theatre
Motown Mania with Groove Marmalade @ Old Mill Toronto
Open Mic Canada Singing Competition @ Yorkgate Mall
Saturday Night Swing Dance with Ben Harvey Combo Plus a Beginner Swing Dance Lesson @ 496 Gladstone Ave
SOARING STRINGS/ Dvorak's Love Letter @ George Weston Recital Hall, Meridian Arts Centre
SuicideBoys - Grey Day Tour @ Budweiser Stage
The Rolling Stones Experience ft The Blushing Brides @ The Pilot
What is Divine? @ Heliconian Hall, 35 Hazelton Avenue, Toronto
Xenia Concerts and TO Live Present: Eliana Cuevas & Jeremy Ledbetter @ 5040 Yonge Street

🎉 Entertainment
13 RoomsA one-of-a-kind Halloween experience awaits you at 13 Rooms, where you walk through 13 different immersive experiences that may just have you running for your life. From live actors to cinematic effects, this Halloween exhibition is just what you need to see i @ Cloverdale Mall
A Better Tomorrow II @ Fox Theatre
A Sushi & Shawarma - Standup Comedy Show @ Free Times Cafe
All of Our Parents Are Immigrants: Comedy Show @ Sweet Action Theatre
Asian Comedy All-Stars with James Roque! @ Rivoli
DJ NV x The Lady Konswallow @ The Painted Lady (Free)
Euchre Night at Red Tape Brewery - New & Experienced Gameplay @ Red Tape Brewery
Mammoth Season! @ Wychwood Theatre
Nights of Lights @ CF Sherway Gardens
Pillow Fright! Presents: Paranormal Activity @ Hot Docs Cinema
The Toronto Halloween Show @ Queen Elizabeth Building, Exhibition Place
Water/Fall Festival @ Toronto waterfront

🎭 Art and Culture
Abscission @ Canadian Music Centre
Adult Crafternoon: Collage Art @ Lillian H. Smith Library
Akin Richmond-Bathurst Open Studio @ Akin Richmond Bathurst
Art Market and Fabric Sale @ Textile Museum of Canada (Free)
Ase Community Foundation 5th Anniversary Gala and Awards @ Delta Hotel Toronto, 75 Lower Simcoe St, Toronto, ON M5J 3A6
Canadian Opera Company Open House @ Four Seasons Centre for the Performing Arts (Free)
Copper Canopy @ Harbourfront Centre
Crochet Level One: Laces @ Bata Shoe Museum
Gatsby Redux @ 235 Queens Quay West
Holbein Acrylic Family Workshop @ ARTiculations Art Supply
North Toronto Group of Artists Fall Tour & Sale @ Multiple Venues (Free)
Paint & Sip - Paint Night - Colorful Pastel Beach Sunset Waves Acrylic Painting @ Fresh Paint Studio Danforth East
Pixels inPrint: A Lego Exhibition @ The inPrint Collective
Scented Candle Making Workshop @ Artbox Studio Gallery
The Word On The Street Toronto @ David Pecaut Square, 215 King St W, Toronto

🎡 Family
A Pumpkin Pillow Making Experience @ ARTBOX
Beginner Auto Maintenance Workshop @ Davenport Perth Neighbourhood & Community Health Centre
Harvest Festival 2025 @ Scadding Court Community Centre
How to Teach Your Kids About Money @ Palmerston Library
National Drive Electric Month - EV event @ Consumer for consumer event (Free)
Ontario Universities' Fair @ Metro Toronto Convention Centre
Study in UK's UK University Fair 2025 @ Hyatt Regency
TPOM Twice Loved Sale @ Dennis R. Timbrell Recreation Centre

🐾 Pet
Grand Opening - Tails Farewell Downtown Toronto @ Tails Farewell Downtown Toronto

📅 Other Events
The Big Magical Cult Show @ The Randolph Theatre
The Bulwark Live @ The Royal

Sunday 09/28

🍽️ Food and Drinks
COOKING CLASS: Full-Day Croissants & Viennoiserie Intensive by Leo Baduria @ The Depanneur
SOUPALICIOUS DUKE Heights 2025 @ Champagne Centre (Free)
Toronto Garlic Festival @ ON Spadina Road between Davenport Road and Dupont street, Toronto (Free)

🎵 Music
CONGRESO FLAMENCO - September Tablao 2025 @ Rivoli
Dark Angel @ The Phoenix Concert Theatre
Opera Revue at Granite Brewery @ Granite Brewery
Shawn Mendes - On The Road Again Tour @ Budweiser Stage
The Spirit of Patsy Cline @ The Pilot

🏒 Sports
MLB: Toronto Blue Jays vs. Tampa Bay Rays @ Rogers Centre

🎭 Art and Culture
Big Stories in Little India Community Event @ The Leslieville Farmers' Market (Free)
Fashion Brunch @ Avant Garde Gallery
Paint & Sip - Paint Night - Dynamic Northern Lights Acrylic Painting @ Fresh Paint Studio Danforth East
Poetry Workshop With Laboni Islam in High Park @ High Park Nature Centre
Queers Poets Clowns - Open Mic @ Tranzac Club
TCBS: Toronto Comic Book Show @ Montecassino Hotel and Event Centre
Textured Art Workshop by Artbox @ Artbox

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Hope you enjoy your weekend ❤️

Zoe
Chief Fun Officer @ Toronto Events Weekly