upcoming events
There’s always something spinning at Cassette. From live sets and DJ nights to drag dinners and karaoke takeovers, our stage never sits still for long.
Catch a local artist before they blow up, sing your heart out after one too many martinis, or settle in for a night that turns dinner into a dance floor.
We’re adding new events all the time, and the best nights are usually the ones you didn’t plan for. Check back often.
Happy Hour
4 PM – 6 PM | Tuesday – Saturday
$5 Off Martinis
Every Thursday
Half-Priced Wine
Select bottles | Every Wednesday
Weekend Brunch Sessions
Brunch served 7AM - 3PM | Saturday & Sunday (Live music Sundays only)
Movie Trivia
Letterboxd has everyone thinking they’re a film buff 🙄
Movie Trivia Night is where you prove it.
Put your movie knowledge to the test, compete for great prizes, and enjoy delicious drinks and bites along the way.
🏆 First-place team wins a $100 gift card to Cassette
🎟 Tickets available on Eventbrite
Dayo Bello Live at Cassette
Dayo Bello returns to Toronto for an intimate, soul-soaked live set—joined by Amaka and new sounds from his latest project, DB.
Departure Secret Show
Departure is transforming Toronto into a city-wide music moment. Make your way to Cassette and be part of the buzz with a secret live show featuring:
Departure x @indie88toronto
Catch a series of acoustic live performances during Departure, in partnership with Indie88 featuring:
Departure Artist Showcase
Make Cassette part of your Departure lineup and step into a music filled night that hits all the right notes. Join us for a live show on May 9 featuring:
Brunch Sessions: Mother's Day Edition
Enjoy a special Mother’s Day Brunch at Cassette where great food and thoughtful moments come together.
What to expect:
Live music throughout the afternoon
Family-style mimosas + $10 espresso martinis
Flower market pop-up by Fondly Floral Designs
A vibrant atmosphere
Shirley Whalen LIVE COMEDY Album Recording - Presented by Howl & Roar!
Shirley Whalen brings her sharp, unfiltered comedy to Cassette for a live album recording—two shows, cold cocktails, and a stacked lineup of local talent.
Shirley Secretaries Chess Club
Come by for a night of chess, music, and pints. Battle it out or just hang back with friends. No cover, all skill levels welcome.
Gladstone Art Exhibit & After Party
In partnership with CONTACT Photography Festival, Gladstone House celebrates the launch of new art installations throughout it’s public spaces. View exhibit details here. All are welcome to attend from. Free entry, please RSVP here.
Starting at 8PM, join us for an after party at Cassette featuring live music, drinks, and a vibrant mix of artists, creatives, and community. Walk-ins only from 8PM onward.
Tumako: Live at Cassette
Join us for an electrifying evening of live funk, soul, and a touch of afrobeat, featuring the dynamic sounds of Tumako.
And just like the best things in life, this event is free.
Make a night of it and stop by for dinner beforehand featuring our new menu and curated sips.
Cassette Karaoke
Step up to the mic at our weekly karaoke night. 9pm-12am. No cover.
Expect late nights, crowd favourites, and a room that knows every word. Whether you're here to perform or just sing along, this is your excuse to stay out a little longer.
Reservations available, walk-ins welcome.
Brunch Sessions at Cassette
Join us for a special brunch experience on weekends at Cassette, featuring live music every Sunday and all your favourite brunch classics. Sip on coffee or cocktails, gather with friends, and savour every bite as you settle into a lively, feel-good atmosphere.
10am-3pm. Reserve your spot on OpenTable.
Project Hail Mary Trivia
Step into the world of Project Hail Mary for a cosmic trivia night that’s anything but ordinary. Think you’ve got what it takes to save the mission?
🏆 First place team scores a $100 gift card (and ultimate bragging rights)
The Canadiana Band
Enjoy Canadian classics live at Cassette.
The Canadiana Band rocks the stage with timeless favourites from Blue Rodeo and Neil Young to The Hip, Bryan Adams, and more.
Free entry. Reservations available, walks in welcome.
Cassette Karaoke
Step up to the mic at our weekly karaoke night. 9pm-12am. No cover.
Expect late nights, crowd favourites, and a room that knows every word. Whether you're here to perform or just sing along, this is your excuse to stay out a little longer.
Reservations available, walk-ins welcome.
Brunch Sessions at Cassette
Join us for a special brunch experience on weekends at Cassette, featuring live music every Sunday and all your favourite brunch classics. Sip on coffee or cocktails, gather with friends, and savour every bite as you settle into a lively, feel-good atmosphere.
10am-3pm. Reserve your spot on OpenTable.
Invisible Friends: AI Motion Design Day for Artists & Builders At Toronto Tech Week
A hands-on generative AI workshop and networking night for artists and creatives—explore new tools, build visual concepts, and connect as part of Toronto Tech Week.
The Boys Trivia
Celebrate the final season of The Boys with a night of trivia at Cassette, hosted by Quizmaster Jess. Expect ruthless questions and zero mercy, just how the Boys would want it.
🏆 1st place team wins a $100 gift card.
Davie Studios presents: Blues
An intimate evening of live blues from the legendary Davie Studios.
This is a ticketed event — Eventbrite coming soon!
Cassette Karaoke: Live Band Edition with Good Enough Live Karaoke!
Take the stage at our monthly live band karaoke hosted by Good Enough Live Karaoke!
9pm-12am. No cover. Sing your heart out with a full band backing you, where the crowd knows every word, and the night builds into an all-out singalong you won’t want to leave.
Reservations available, walk-ins welcome.
Brunch Sessions at Cassette
Join us for a special brunch experience, featuring live music every Sunday and all your favourite brunch classics. Sip on coffee or cocktails, gather with friends, and savour every bite as you settle into a lively, feel-good atmosphere.
10am-3pm. Reserve your spot on OpenTable.
Brunch Sessions at Cassette
Join us for a special brunch experience on weekends at Cassette, featuring live music every Sunday and all your favourite brunch classics. Sip on coffee or cocktails, gather with friends, and savour every bite as you settle into a lively, feel-good atmosphere.
10am-3pm. Reserve your spot on OpenTable.
Cassette Karaoke
Step up to the mic at our weekly karaoke night. 9pm-12am. No cover.
Expect late nights, crowd favourites, and a room that knows every word. Whether you're here to perform or just sing along, this is your excuse to stay out a little longer.
Reservations available, walk-ins welcome.
Closed for Private Event
Closed for the evening.
Catch us tomorrow for Karaoke night or end off the week with Sunday brunch & live music.
Basketball & Bag Charms
Get ready for the ultimate girls’ night out - where basketball meets creativity! Join us for a fun, beginner-friendly bag charm workshop while celebrating the very first preseason game of the Toronto Tempo. Hosted by Hobby Hub Life.
🎟️ Tickets are $45. Includes all materials and a free mixed drink or beer. Buy 3 tickets, get 1 free.
Brunch Sessions at Cassette
Join us for a special brunch experience on weekends at Cassette, featuring live music every Sunday and all your favourite brunch classics. Sip on coffee or cocktails, gather with friends, and savour every bite as you settle into a lively, feel-good atmosphere.
10am-3pm. Reserve your spot on OpenTable.
Cassette Karaoke: Live Band Edition with Good Enough Live Karaoke!
Take the stage at our monthly live band karaoke hosted by Good Enough Live Karaoke!
9pm-12am. No cover. Sing your heart out with a full band backing you, where the crowd knows every word, and the night builds into an all-out singalong you won’t want to leave.
Reservations available, walk-ins welcome.
Davie Studios Presents: Blues
Enjoy an intimate and sentimental evening of live jazz. Blues is Davie Studios' 5th project featuring a small quartet with Toronto's best jazz musicians, playing some of your favourite moody and romantic sounds.
This event is sold out — join the waitlist here
DJ Campuruso
DJ Campuruso takes over the decks with a cassette-only set, spinning merengue, reggaeton, and salsa straight from his mixtape collection. No cover.
Come by for dinner or drinks beforehand. Reservations available, walk-ins welcome.
Hannah Montana Trivia
Built for superfans—an all-out Hannah Montana trivia night celebrating 20 years of the show, packed with iconic moments, throwback hits, prizes, and peak best-of-both-worlds nostalgia.
🎟️ Grab your ticket on Eventbrite
Brunch Sessions at Cassette
Join us for a special brunch experience on weekends at Cassette, featuring live music every Sunday and all your favourite brunch classics. Sip on coffee or cocktails, gather with friends, and savour every bite as you settle into a lively, feel-good atmosphere.
10am-3pm. Reserve your spot on OpenTable.
Cassette Karaoke
Step up to the mic at our weekly karaoke night. 9pm-12am. No cover.
Expect late nights, crowd favourites, and a room that knows every word. Whether you're here to perform or just sing along, this is your excuse to stay out a little longer.
Reservations available, walk-ins welcome.
High School Crush
Step into a time capsule featuring early 2000s pop as High School Crush makes their debut at Cassette. From iconic anthems to forgotten favourites, this cover brand brings pure millennial nostalgia.
Doors open 8PM, show starts at 8:30PM. Three sets. Free entry.
A Night With Ania Hoo
For the soulful, the sweet, and the real lovers of R&B: join us at Cassette for a sonic journey through love and lyrics. Witness the magic of Ania Hoo and her latest single “Make Me Up”, live in an intimate setting as Lovers Rotation & Girls Luv R&B bring that late-night R&B energy out of the speakers and into the room.
Expect a night of dancing, connection, giveaways and awe as Ania transports you to another plane.
🎟️ Purchase your ticket here
Open Ended: Live Storytelling
Open Ended is a live storytelling night about unfinished moments — and the endings we imagine together. Writers and first-time storytellers share real or imagined stories without closure, then the audience steps up to the mic to freestyle an ending.
🎟️ Grab your ticket on Eventbrite
Brunch Sessions at Cassette
Join us for a special brunch experience on weekends at Cassette, featuring live music every Sunday and all your favourite brunch classics. Sip on coffee or cocktails, gather with friends, and savour every bite as you settle into a lively, feel-good atmosphere.
10am-3pm. Reserve your spot on OpenTable.
Cassette Karaoke
Step up to the mic at our weekly karaoke night. 9pm-12am. No cover.
Expect late nights, crowd favourites, and a room that knows every word. Whether you're here to perform or just sing along, this is your excuse to stay out a little longer.
Reservations available, walk-ins welcome.
Stuart Brignell's Unspoken Souls
Get ready for a night of moody jazz and neo soul with Stuart Brignell's Unspoken Souls.
Free entry. Reservations available & walks in welcome.
Poured & Bound: Book Swap
This literary tasting invites guests to experience books the way you might sample a flight of wine—through excerpts, themes, and guided discussions designed to spark connection and lively debate.
🎟️ Grab your ticket on Eventbrite
Movie Trivia
Letterboxd has everyone thinking they’re a film buff 🙄
Movie Trivia Night is where you prove it.
Put your movie knowledge to the test, compete for great prizes, and enjoy delicious drinks and bites along the way.
🏆 First-place team wins a $100 gift card to Cassette
🎟 Tickets available on Eventbrite
Cassette Karaoke
Step up to the mic at our weekly karaoke night. 9-12pm. No cover.
Expect late nights, crowd favourites, and a room that knows every word. Whether you're here to perform or just sing along, this is your excuse to stay out a little longer.
More details dropping soon.
Easter Brunch
Join us for a special brunch experience on Saturday, April 4 and Sunday, April 5 featuring live music and all your favourite classics. Sip on coffee or cocktails, gather with friends, and savour every bite as you settle into a lively, feel-good atmosphere.
Reserve your spot on OpenTable.
He’s the DJ, I’m the Drummer
Settle in for a night built on rhythm and movement with @djadverb behind the decks and @true7self on the drums. Expect an evening that unfolds in layers—elevated, energetic, and effortlessly in sync.
No cover. All vibes. Bring your crew and enjoy crafted sips & bites while your at it.
Seinfeld Trivia
What’s the deal with trivia night?
Join us for Seinfeld Trivia hosted by @philipp.a.a — a night of big laughs, and even bigger bragging rights.
Winner takes home a $50 Cassette gift card + $30 for the best breakfast sandwich joint in the city — @dads.goodmorning
No soup for you… unless you win.
Saturday Sound Sommelier
Our Saturday Sound Sommelier keeps the energy flowing till late, creating the perfect atmosphere for hanging with friends over tasty bites, signature cocktails, and curated sounds. 🍸🎶
No cover, all vibes. Reserve your spot on OpenTable or drop in for a spontaneous night out.
Davie Studios presents: Blues
Enjoy an intimate and sentimental evening of live jazz at Cassette. Blues is Davie Studios' 5th project featuring a small quartet with Toronto's best jazz musicians playing some of your favourite moody and romantic sounds.
Grab your ticket on Eventbrite.
Bridgerton Trivia
You are cordially invited to an evening of wit, whispers, and well-placed wagers, in honour of the ever-scandalous world of Bridgerton. Gather your most clever companions and prepare to prove your knowledge.
The victorious team shall be rewarded handsomely with a $100 Cassette gift card.
Tickets available now on Eventbrite.
Closed for Private Event
Closed for the evening.
Catch us next week for Bridgerton trivia, moody blues and Saturday sounds or simply come by for dinner and curated sips.
The Canadiana Band
Enjoy Canadian classics live at Cassette.
The Canadiana Band rocks the stage with timeless favourites from Blue Rodeo and Neil Young to The Hip, Bryan Adams, and more.
Free entry. Reservations available, walks in welcome.
Kansei Comedy
Kansei Yasuda is a bit like Superman—mild-mannered at the Gladstone House front desk, but secretly a comedian so funny that Kill Tony judges said he could make the back of a Cheesecake Factory menu hilarious. Catch him every month at Cassette.
Joining him for his March show is a surprise special guest. Hint: he’s a rising star in the Toronto comedy scene currently on a 44-city tour, and featured in the hit series The Office Movers.
No cover. Reservations available, walk-ins welcome.
Saturday Sound Sommelier
Discover Toronto’s best DJs every Saturday night at Cassette. Our Saturday Sound Sommeliers keep the energy flowing till late, creating the perfect atmosphere for hanging with friends over tasty bites and signature cocktails. 🍸🎶
No cover, all vibes. Reserve your spot on OpenTable or drop in for a spontaneous night out.

