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
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.
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.
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.
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.
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.
Saturday Sound Sommelier
Discover Toronto’s best DJs every Saturday night. 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.
Mending Night
Join us for Mending Night: a hub for community building where volunteers fix your clothes. Grab a bite, connect with your neighbours and enjoy good tunes.
Free to attend & mending offered at no additional cost.
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 from 10am-3pm. 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.
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.
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
Poured & Bound: A Boozy Book Club
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.
This is a ticketed event — Eventbrite coming soon.
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.
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.
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.
This is a ticketed event — Eventbrite coming soon.
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.
Campuruso
DJ Campuruso takes over the decks with a cassette-only set, spinning Latin, reggaeton, and salsa straight from his mixtape collection. No cover.
Come by for dinner or drinks beforehand. 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 is a ticketed event — Eventbrite coming soon.
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.
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.
Stuart Brignell's Organ Trio: Live at Cassette
Get ready for a night of soulful grooves and high-energy jazz with Stuart Brignell's Organ Trio. Blending shuffle blues, funky RnB, jazz, and hints of hard bop.
Free entry. Reservations available & walks in welcome.
Poured & Bound: A Boozy Book Club
This literary tasting hosted by Poured & Bound 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
Shirley Secretaries Chess Club
Vanquish your foes to a soundtrack provided by some of the cities best up and coming DJ’s, or just hang back and watch while enjoying some good food and a pint. All skill levels welcome. Brought to you by the boys at Secretaries and Shirley Company.
Book a table or walk in. No cover.
Olivia Dean Women's Day Tribute Show
We’re wrapping up our Olivia Dean love song series with one final evening in celebration of International Women’s Day. Date night, friends, or solo — all love is welcome. 💖
Grab your tickets on Eventbrite
Saturday Sound Sommelier
Enjoy a taste of 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.
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.
Dominoes Party
Pull up to aproperdominoesparty at Cassette (not the pizza 🍕) and celebrate Tyrell Maclennan featuring good energy, curated sounds and a little friendly competition.
Everyone’s welcome. No cover. Just vibes.
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
Saturday Sound Sommelier: DJ h0mie (Vinyl Hybrid Set)
Our expert sound sommelier’s will undoubtedly find the perfect pairing for all of our tasty bites and delicious cocktails.
No cover, all vibes!
Reserve a seat on OpenTable
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.
Heated Rivalry Trivia
Try to not fall in love with your opponents at the most competitive night in trivia history. Come test you knowledge on the hottest novel and TV series with Quizmaster Jess for a chance to win some great prizes, including a $100 gift card! Don’t forget to try one of our specialty signature cocktails and food only available during Heated Rivalry trivia!
Tickets are available at Eventbrite, but hurry up because the other 10 (!) have sold out.
Heated Rivalry Trivia
Try to not fall in love with your opponents at the most competitive night in trivia history. Come test you knowledge on the hottest novel and TV series with Quizmaster Jess for a chance to win some great prizes, including a $100 gift card! Don’t forget to try one of our specialty signature cocktails and food only available during Heated Rivalry trivia!
Tickets are available at Eventbrite, but hurry up because the other 10 (!) have sold out.
Heated Rivalry Trivia
Try to not fall in love with your opponents at the most competitive night in trivia history. Come test you knowledge on the hottest novel and TV series with Quizmaster Jess for a chance to win some great prizes, including a $100 gift card! Don’t forget to try one of our specialty signature cocktails and food only available during Heated Rivalry trivia!
Tickets are available at Eventbrite, but hurry up because the other 10 (!) have sold out.
Saturday Sound Sommelier: Switch B (Vinyl)
Our expert sound sommelier’s will undoubtedly find the perfect pairing for all of our tasty bites and delicious cocktails.
No cover, all vibes!
Reserve a seat on OpenTable
Olivia Dean Valentine’s Tribute - Night 2
So nice we had to do it twice ♥️ Due to our sold out show on Feb 15, we’ve dropped a second night dedicated to Olivia Dean’s love songs. Whether you come with a partner, a friend, or a solo date, all love is welcome to enjoy.
Get your tickets at Eventbrite!
Rewind at Cassette: A Dinner Show with Tynomi Banks
Join legendary drag performer Tynomi Banks for dinner, music, and all the hits from the 80s, 90s, and 2000s. A night of pure fun and feel-good energy.
Tickets available on OpenTable
Heated Rivalry Trivia
Try to not fall in love with your opponents at the most competitive night in trivia history. Come test you knowledge on the hottest novel and TV series with Quizmaster Jess for a chance to win some great prizes, including a $100 gift card! Don’t forget to try one of our specialty signature cocktails and food only available during Heated Rivalry trivia!
Tickets are available at Eventbrite, but hurry up because the other 10 (!) have sold out.
Bridgerton Trivia
Dearest readers, it is with the utmost pleasure and the most scandalous of intentions that I bid you welcome to an evening of revelry and intrigue, dedicated to none other than the illustrious world of Bridgerton.
Questions will be on seasons 1- 4 Part 1 of the Bridgerton TV show (Part one comes out Jan 29, Part 2 comes out Feb 26 only on Netflix).
First place team wins a $100 gift card to Cassette.
Tickets available at Eventbrite
Heated Rivalry Trivia
Try to not fall in love with your opponents at the most competitive night in trivia history. Come test you knowledge on the hottest novel and TV series with Quizmaster Jess for a chance to win some great prizes, including a $100 gift card! Don’t forget to try one of our specialty signature cocktails and food only available during Heated Rivalry trivia!
Tickets are available at Eventbrite, but hurry up because the other 10 (!) have sold out.
Olivia Dean Valentine’s Tribute
Join us for a Valentine's Tribute Show of all Olivia Dean love songs
Whether you come with a partner, a friend, or a solo date, all love is welcome ❤️
The Soul Suite - Valentine's Brunch
A space where music connects good food, good music and even better company.
“The Soul Suite” offers an intimate and immersive musical experience, blending timeless classics with modern day grooves. This valentine's edition is for the R&B lovers featuring a curated brunch menu and live music.
Grab your ticket on Eventbrite - two sessions available: 11am & 2pm
Valentine's Dinner ft. Leo Orlov
Love is in the air, and in every pour. 🍷
This Valentine’s, enjoy 1/2-price bottles of wine, food and cocktail features, and a live guitar performance by Leo Orlov to set the mood with your special someone.
Reservations available, walks in welcome.
Mira Méla
Spend your Friday night with Toronto underground soul singer Mira Méla. The vocalist, songwriter, and keys player with deep jazz roots will beautifully blend the sounds of smoky neo-soul, motown-pop, and late-night R&B for a Valentine’s weekend performance you won’t want to miss.
Her and her band will being pairing reimagined classics (Maxwell, MJ, Roy Ayers) with her own original catalog, including tracks from her forthcoming debut EP for a lush tribute to soul’s golden era with a modern heart.
Cover is $10, with advance tickets available on OpenTable
Heated Rivalry Trivia
Try to not fall in love with your opponents at the most competitive night in trivia history. Come test you knowledge on the hottest novel and TV series with Quizmaster Jess for a chance to win some great prizes, including a $100 gift card! Don’t forget to try one of our specialty signature cocktails and food only available during Heated Rivalry trivia!
Tickets are sold out, but join the waitlist on Eventbrite for a chance to play!
Shirley Secretaries Chess Club
Join us at Cassette for a night of chess, music, and pints. Battle it out or just hang back with chicken tenders and enjoy. No cover, all skill levels welcome.
Heated Rivalry Trivia
Try to not fall in love with your opponents at the most competitive night in trivia history. Come test you knowledge on the hottest novel and TV series with Quizmaster Jess for a chance to win some great prizes, including a $100 gift card! Don’t forget to try one of our specialty signature cocktails and food only available during Heated Rivalry trivia!
Tickets are sold out, but join the waitlist on Eventbrite for a chance to play!
Heated Rivalry Trivia
Try to not fall in love with your opponents at the most competitive night in trivia history. Come test you knowledge on the hottest novel and TV series with Quizmaster Jess for a chance to win some great prizes, including a $100 gift card! Don’t forget to try one of our specialty signature cocktails and food only available during Heated Rivalry trivia!
Tickets are sold out, but join the waitlist on Eventbrite for a chance to play!
Watch The Game 🏈
Join us for the Big Game at Cassette with food features, $5 pints, and a lively crowd from kickoff to the final play. Come early and make a night of it.
Reservations available, walks in welcome.
Saturday Sound Sommelier: Sayyzon
Our expert sound sommelier’s will undoubtedly find the perfect pairing for all of our tasty bites and delicious cocktails.
No cover, all vibes!
Reserve a seat on OpenTable