Toronto Festivals & Events for Next Week (Sep 21 - Sep 27)

Toronto Festivals & Events for Next Week (Sep 21 - Sep 27)

Monday 09/21

🍽️ Food and Drinks
Five Day Cake Baking & Decorating Masterclass @ Le Dolci Culinary School
MONDAYS WITH MAMA ROSA @ 7 Numbers Eglinton
Question Everything Trivia @ CIBC Square l drinks with your coworkers just got interesting @ CIBC Square (Free)
Time Travelling Tastes @ Dorsay Community & Heritage Centre

🎵 Music
Sex Pistols - 50 Years of Punk Tour @ History Toronto
Staind, Seether, Hoobastank & Hinder - Break The Cycle Anniversary Tour 2026 @ RBC Amphitheatre
With Heaven On Tour - Zach Bryan @ Rogers Centre

🎉 Entertainment
A Group Therapy Comedy - Standup Comedy Show @ Chakhna (Free)
LIVE THRU THIS @ Comedy Bar
Vanderpump Rules Trivia @ Hemingway's

🏒 Sports
Sonnie Trotter @ MEC Toronto @ MEC Toronto

🎭 Art and Culture
AI Evenings TO: How AI is Amplifying Creativity Across Product, Design, and Marketing @ BrainStation Toronto
INTERNATIONAL PEACE FESTIVAL - FESTIVAL INTERNATIONAL DE LA PAIX 2026 @ Multiple Venues

🎡 Family
Test Drive for Change: Support SickKids with a Test Drive at Old Mill Cadillac @ OLD MILL CADILLAC

Tuesday 09/22

🍽️ Food and Drinks
C4 Cocktail Hour - Elevate Festival Edition @ Mademoiselle Raw Bar + Grill

🎵 Music
2000's Emo Music Trivia Night - Snakes & Lattes College @ Snakes and Lattes College
How Shall I Sing That Majesty? Music Lecture & Workshop Series @ Christ Church Deer Park
KARAOKE - 3rd Anniversary - NO COVER @ Ground Control - 1279 Queen St. W. (Free)
Tuesday Nights at The Reservoir Lounge with Janice Hagan @ The Reservoir Lounge
With Heaven On Tour - Zach Bryan @ Rogers Centre

🎉 Entertainment
Always Sunny Trivia Night @ Dublin Calling Adelaide Hosted by Trivia Kings @ Dublin Calling
Blood on the Clocktower - Intermediate - at Twilight Cafe Yonge & Bloor @ Twilight Cafe - Yonge & Bloor
Book Trivia: The Love Hypothesis @ Hemingway's
Elevate Festival @ 1 Front St East
Question Everything Trivia @ Mascot Brewery @ Mascot Brewery Etobicoke
Question Everything Trivia @ Thai Tavern l quizmaxxing on a tuesday bc ynot @ Tha Phae Tavern

🎭 Art and Culture
A Glow-in-the-Dark Paint Night - TUESDAY DEAL! @ ARTBOX
Darren Greer BOOK LAUNCH : The Range Rules @ Glad Day Lit
Judged Before The Judge - Official Premiere @ Paradise Theatre
Multi-Species Noticing & Indigenous Stories w/ Ariel Sim & Trina Moyan @ STILL/ALIVE
Something sweet is coming for Cybersecurity Awareness Month @ Union Station - UP Express
The Muses Autumn Equinox: Women's Circle & Open Mic @ Cherry Beach
To a Flame @ 877 Yonge St, Toronto, ON M4W 3M2

🎡 Family
Breaks and Brews: Morning Birds and Coffee Walk @ Humber Arboretum

📅 Other Events
Avedon Aging: An Evening with Adam Gopnik @ The Image Centre
Costumed Life Drawing @ Gwartzman's Art Supplies
The Making of She Holds Up the Stars @ Toronto Public Library, North York Central Branch

Wednesday 09/23

🎵 Music
HAMILTON Karaoke & Sing-Along @ Lula Lounge

🎉 Entertainment
Bad and Boozy Bingo @ Lost Craft Brewery l bingo for people who don't play bingo @ Lost Craft Brewery
FREE Survivor 51 Premiere Watch Party @ The Pilot (Free)
Funny Pho Show - A Stand-Up Comedy Show @ Dzo Viet Eatery (Free)
HeHeHeated Rivalry @ Tallboys
Parks and Rec Trivia @ Hemingway's
Pub Trivia @ Bar Wellington
Question Everything Trivia @ Ambassador Pizza Co.
Question Everything Trivia @ Insomnia
Question Everything Trivia @ Courage Cookies at Stackt Market
Speed Puzzle Competition @ Twilight Cafe - Midtown
The History of Concrete - Special Advance Screening @ Hot Docs Ted Rogers Cinema

🏒 Sports
Toronto Maple Leafs vs. Ottawa Senators: Preseason Game @ Scotiabank Arena

🎭 Art and Culture
Braid and Sip @ Nu Yu Salon
Canvas Chronicles @ Etobicoke Civic Centre Art Gallery (Free)
Close Encounters: Barry Ace on Angus Trudeau @ Art Gallery of Ontario (Free)
Historical Walking Tour - Much Memories of 299 Queen W @ Sidewalk opposite 299 Queen W
Robyn Rennie: A Discussion on Blindness Arts, Disability Culture, and Creative Approaches @ Toronto Public Library Brentwood Branch
Willow Leaf-Shaped Weaving w/ Graham Teeple at STILL/ALIVE @ STILL/ALIVE
Women of Wampum @ Onsite Gallery

🎡 Family
Infant CPR and First Aid Training @ kāer
National Tree Day Nature Walk in Toronto's High Park @ High Park Nature Centre

📅 Other Events
In Residency with Groupe Barroco @ Fairmont Royal York
Investor Connect Pitch Deal Flow Night Toronto @ Blood Brothers Brewing
Sound Bath for Writers @ Jungle Flower Wellness
Tech Talks at Staples - Windows for Future Ready Learning @ Staples Canada

Thursday 09/24

🍽️ Food and Drinks
INSTITUT 022 : BY THE WINDOW @ INSTITUT
Perch: Soil/Land/Sea with Chef Justin Champagne-Lagarde @ The Depanneur
Reid's Mocktail Workshop - SOBR Market x Reid's Distillery @ Reid's Distillery

🎵 Music
IN Session Presents Closer @ Ace Hotel Toronto
Nation of Language: 2026 Tour @ The Danforth Music Hall
Second Summer Music Festival 2026 @ Multiple Venues

🎉 Entertainment
Behind the Curtain at Alumnae Theatre @ Alumnae Theatre

Joe List @ Randolph Theatre
Question Everything Trivia @ Fortunate Fox @ Fortunate Fox
Red Richardson - Just For Laughs Toronto @ Comedy Bar East
Turning Forty: a women's workshop in Arabic @ 3 Summerland Terrace

🎭 Art and Culture
Art Bash 2026 @ Art Gallery of Ontario
Behind the Curtain at Alumnae Theatre @ Alumnae Theatre
Documentary Screening: Wilfred Buck @ Palmerston Library (Free)
FREE Documentary Screening: Wilfred Buck @ Palmerston Library (Free)
Free Screening of The Zoongidewin Project @ Hot Docs Cinema (Free)
Mari Torocsik Hungarian Film Festival @ Multiple Venues
Oil Painting Rainy Fall Eve @ Artbox
Orphan @ Carlton Cinema
RUTAS International Festival of Performance @ Multiple Venues
The Nature Cure - paintings by Elizabeth Lennie @ Muse Gallery
Wellbeing Walks: River Resonances by Treva Legassie @ Lassonde Art Trail

🎡 Family
Toronto Zoo - Boo at the Zoo @ Toronto Zoo

🐾 Pet
Toronto Dog Moms x Barks & Books Club: End Of Summer Hang @ Ivy Coffee

📅 Other Events
Living Beauty x 444 Walk Club @ Living Beauty
Question Everything Trivia @ Fortunate Fox l thursdays got a friday glow up @ Fortunate Fox
Turning Forty: a women's workshop in Arabic @ 3 Summerland Terrace

Friday 09/25

🍽️ Food and Drinks
Cafe Milk O'Clock @ Queen and Shaw
Etobicoke Ribfest 2026 @ Colonel Samuel Smith Park
GLB Beer Week Launch @ The Only Cafe
Modern Seoul by Jon Lee @ The Depanneur

🎵 Music
5 Year Anniversary Festival @ Wiggle Room
2026 The Gathering Tour - Weezer @ Scotiabank Arena
ALISHA @ NOMAD @ NØMAD
Autograf @ Future Nightclub
Beethoven & Farrenc @ TBA
Blood Moon Rave @ Tapestry Bar, Toronto, 224 Augusta Ave
BORNS with Two Feet & The Blue Stones - Live At The Bowl @ The Bowl at Sobeys Stadium
EXIT POINTS #76 @ Arraymusic
FREE - Outdoor music festival @ The Bentway (Free)
L.A.'s Free Live Concert @ Hoops on Yonge (Free)
Lughnasadh Music Festival @ The Corleck
Madonna Fest 2026 - All Madonna All Night @ Ground Control
Performers4Palestine @ Ukrainian Catholic Church of the Holy Protection
Royal Botanical Gardens' Fall Concert: Patrick Watson @ Royal Botanical Gardens

🎉 Entertainment
5th Annual Women Empowerment Awards @ Fairmont Royal York
Autumn Equinox Sound Bath @ TBA
Cafe Comedy @ Osprey Cafe
Full Moon in Aries Hammock Sound Bath @ Jungle Flower Wellness
Halloween Haunt at Canada's Wonderland @ Canada's Wonderland
It's in the Cards: A Toronto Social Night for Adults 30 and up @ TacoTaco
Kylie Cosmetics Moodstones Collection Pop-Up @ 486 Front St W, Toronto, ON M5V 0V2
Liberty Laughs Comedy Show Every Last Friday of the Month @ Liberty Village Market and Cafe
Question Everything Trivia @ 10 DEAN - Sloane @ 10 DEAN | Sloane
Question Everything Trivia @ GRETA @ Greta Bar Toronto
Rachel Feinstein - Just For Laughs Toronto @ Comedy Bar East
Red Flags & Laughs - Date Night Standup Comedy Show @ Chakhna
The Celestial Seed - A Premium Dungeons & Dragons One-Shot Experience @ Left Field Brewery Liberty Village
The Liberty Laughs Comedy Show - Friday September 25 @ Liberty Village Market and Cafe

🏒 Sports
MLB: Toronto Blue Jays vs. Cincinnati Reds @ Rogers Centre
THRIVE: Vegan Health & Fitness @ Centre for Social Innovation
Toronto Pro Wrestling Rock Show! Superkick'd @ The Great Hall

🎭 Art and Culture
Clay Sculpting Session @ ARTBOX
Kamiphony by Cybele Young @ Koffler Arts
Lessons in Objectology by Gord Peteran @ Koffler Arts
Natural Dye Workshop w/ Lizz Aston at STILL/ALIVE @ STILL/ALIVE
Open World Toronto Film Festival 2026: A Celebration of Art, Film & Culture @ Kensington Studio
Riverdale Art Show and Sale @ Riverdale Art and Show Sale
Smileys: A New Play Reading @ Wychwood Theatre
THE FRESH BEATS SERIES BACK IN THE DAY 90s & 00s HIP HOP & R&B PORTRAITS OF CULTURE @ Fresh Paint Studio + Café

🎡 Family
LSG Hobby Warehouse Sale @ Lightspeed Global Warehouse

Saturday 09/26

🍽️ Food and Drinks
Anga's Farm: Fall Sugar Cookie Decorating Workshop @ Anga's Farm & Nursery
Couples Dining: Spanish Tapas at Taberna Social @ Taberna Social
GLB Oktoberfest @ Great Lakes Brewery
Indigenous Food Lab by Chef Taylor Parker @ The Depanneur
Oktoberfest at Rorschach Brewing @ Rorschach Brewing

🎵 Music
26 Sep with CARLOS MENACA from Spain @ Wiggle Room
31 Hour Wiggle Room Anniversary Festival @ Wiggle Room
2026 Canadian Songwriters Hall of Fame Induction Ceremony @ Massey Hall
Duo Perse-Inca @ Spadina Theatre
DUTTY feat...KING TURBO & CHOPPA CHOP @ BSMT 254
Free Times presents Tony Molesworth, A Mystical Musical Evening @ Free Times Cafe
Karaoke Night @ Cassette @ Cassette
Klezmer Jam & Yiddish Dance - September 26! @ High Park Nature Centre
Music Trivia! Name That Tune - 1st night @ Hemingway's
Picastro "Double On Time" Release with Bernice and Granny Smith @ Gloves Up Boxing Gym
Power House: A Mission Concert @ 12Fifty Events Center
Public Image Ltd - This Is Not... The Final PiL Tour @ The Danforth Music Hall
Samba Reggae Percussion Workshop - September Pop-Up @ Studio 330 Geary Ave
Sens, Rhétorique, Musique : Machaut and the Three Gifts of Nature @ St Thomas Anglican Church, Huron Street
September Songs: The Music of Kurt Weill - Restoration Screening & Performance @ Hot Docs Ted Rogers Cinema
Totally 2000's Video Dance Party @ Phoenix Concert Theatre (Free)

🎉 Entertainment
"Food for Thought" Trivia event @ St. James Cathedral Centre, 65 Church St.
2nd Annual Food For Thought Trivia Night @ Cathedral Centre, 65 Church Street, Toronto
100 Percent Canadian Beef: Lake Ontario @ Second City
DAISE Show and Tell @ Toronto Eaton Centre, MAC Court
Heated Rivalry: The Unauthorized Musical Parody Staged Reading @ Randolph Theatre
Pete Davidson @ Meridian Hall
Randy Feltface - Gimmick World Tour @ Winter Garden Theatre
Stef Dag @ Comedy Bar
Tiffany Haddish @ Elgin Theatre
Up in Jokes Toronto Comedy Show Sept 26 at 1350 St Clair Ave West @ The Boardroom Comedy Club

🏒 Sports
MLB: Toronto Blue Jays vs. Cincinnati Reds @ Rogers Centre
The Down There Affair @ The Bentway

🎭 Art and Culture
A Glow-in-the-Dark Paint Night by Artbox @ ARTBOX
Akin Art Crawl: Lassonde Art Trail Tour @ Biidaasige Park (Free)
Block Printing @ Hot Pizza Studio, 134 Osler St.
Drawing, Meditation & Embroidery w/ Verundah at STILL/ALIVE @ STILL/ALIVE
Exhibition "Dakiimi / To have land" by Amber Quail @ Riverdale Hub Gallery
Gatsby Redux @ Harbourfront Centre
Glow-in-the-Dark Paint Pouring on Figurines & Canvas @ ARTBOX
Mari Torocsik Hungarian Film Festival Screenings - Silent Friend @ Carlton Cinema
Nrittamalika 2026 @ York Woods Library Theatre
Open Canvas Project: GATHER Public Reception and Zine Giveaway @ Todmorden Mills Papermill Gallery
Pumpkin Pillow Making Workshop @ ARTBOX
Runway of Rezilience @ Evergreen Brick Works
Slow Down & Connect: Cafe Social, Intuitive Drawing, Journaling, Meditation in the Park @ 280 Spadina Ave., Toronto, ON M5T 1H2
The Conservatory at Gallery 1888 @ Gallery 1888
The Word On The Street Toronto @ David Pecaut Square (Free)
Toronto Biennial of Art 2026, Things Fall Apart @ Multiple Venues
Toronto Burning Man Decompression 2026 - Ascent @ Motorista Studios
Under the Influence: A Writing Workshop @ The World Building Lab
Watercolour Paint Night - Sunflowers and Dragonflies Watercolour Paint Night in Toronto @ Fresh Paint Studio + Café

🎡 Family
Making the Cut - Pruning Workshop with the Etobicoke Master Gardeners @ Humber Arboretum (Free)
Ontario Science Centre - Celebrate Black Excellence 2026 @ Scarborough Town Centre (Free)

🐾 Pet
Dogsville x TDM Day @ Streetsville Village Square
Paint Your Pet Experience @ ARTBOX
The Pup'Kin Patch. Includes hands-on Dog CPR & First Aid Fundamentals certification @ Highpark Gardens

📅 Other Events
Ontario Universities' Fair - OUF 2026 @ Metro Toronto Convention Centre
QS Master's and MBA Event in Toronto @ Marriott Downtown at CF Toronto Eaton Centre (Free)
Toronto stands up for aid: renewing Canada's leadership @ Centre for Social Innovation
Toronto Vintage Show @ Queen Elizabeth Building at Exhibition Place

Sunday 09/27

🎭 Art and Culture
Tristan und Isolde - Opera @ Humber Crest United Church
Anga's Farm: Fall Planter Workshop @ Anga's Farm & Nursery
Artist Walkthrough: Cybele Young @ Koffler Gallery
Author Tonya Walker signs her new novel at Word on The Street Literary Festival @ Word on The Street Festival (Free)
BIRDS OF A FEATHER FLOCK TOGETHER, an exhibition of art by Ukrainian artist Andrii Palval @ Shevchenko Museum
Camerama Camera Show @ Japanese Canadian Cultural Centre
Fall Poetry Workshop with Laboni Islam @ High Park Nature Centre
Glow-in-the-Dark Paint Pouring Workshop @ ARTBOX
In Conversation: Artist Gord Peteran and Curator David Liss @ Koffler
Mari Torocsik Hungarian Film Festival Screenings - In Praise of Older Woman @ Carlton Cinema
OPEN MIC: 100,000 Poets For Change @ Free Times Cafe
Paint Night - Toronto Nights Watercolour Painting Workshop in Scarborough @ Fresh Paint Studio + Café
Reconciliation Walk & Indigenous Art Trail @ The Village at Black Creek
Sacred Womb Circle & Cacao Ceremony @ Inner Arts Collective
SCULPTURAL FLORAL INSTALLATION W/ RHIZOME SERIES @ STILL/ALIVE
Sound Bath for Writers @ Jungle Flower Wellness
The Sublime September Toronto Comic Jam @ The Cameron House
Toronto Cactus & Succulent Club Fall Plants Show and Sale @ Toronto Botanical Garden
Unzipped - 4K Restoration @ Hot Docs Ted Rogers Cinema
Workshop: How to Organize Inclusive Events - with Alex Ketchum @ Glad Day Lit (Free)

🍽️ Food and Drinks
Challah & Babka by Alissa Kondogiannis @ The Depanneur
Toronto Cafe Walk x Conscious Cass - Annex Edition @ The Annex

🎵 Music
Kasango: Harriet's Rooftop Session @ Harriet's Rooftop
Open Opera Experience: Acis & Galatea @ College Street United Church
Sunday SerVice Special Edition Tribute to JOEE CONST @ Wiggle Room
UP in Concert @ The Bowl at Sobeys Stadium

🎉 Entertainment
A Hidden Speakeasy Comedy Show @ TBA
FREE! Comedy & Bingo Night at Delta Etobicoke @ Delta Bingo & Gaming (Free)
Question Everything Trivia @ Insomnia l twice a week because once wasn't enough @ Insomnia
Standup on Sunday @ Comedy Bar
Toronto Rooftop Day Party @ Aera

🏒 Sports
Gentle Fitness Class for Adults Over 50 at Todmorden Mills @ Todmorden Mills Heritage Site
Junction City Wrestling - September 27th, 2026 - Brewtality! @ Rainhard Brewing
MLB: Toronto Blue Jays vs. Cincinnati Reds @ Rogers Centre
Scarborough Link Ride - Close the Gaps @ Warden Hilltop Community Centre

🎡 Family
Little Sprouts - Garden Gnomes & Fairy Homes @ Pickering Museum Village

🐾 Pet
Toronto Dog Moms X Riverside BIA: Paws Walk @ Riverside BIA

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Chief Fun Officer @ Toronto Events Weekly