Happy Hour hits different with a piano. 🎹🍷☀️

$5 glasses of wine. Piano requests. Evening hangs.

Grab a seat, throw in your favourite request and let us soundtrack your happy hour at The Lady.

Come early. Stay later than planned. ✨

A community-driven, safe-space dance party featuring local resident and guest DJs, producers from Toronto's diverse electronic music scene, visuals, and bar-top burlesque.

FREE | 9PM til LATE!

THE MOVEMENT : FOR THE SOUL

For Private School, 3-Step & Deep House Groovers. We got you, come and vibe.

Free RSVP Entry allll night!

Rheostatics founding member Tim Vesely and songwriter-musician Jane Gowan create thoughtful, layered pop songs that pull you in quietly and stay with you long after the set ends. This one is for the song lovers.

7pm | $15

Join us at 10PM for bartop burlesque, DJs, dancing, and just the right amount of trouble. 🍸🔥

🎹3–5 PM —Jelly Roll Piano Jam
✨ Hosted by Windsor Johnson @windsor_johnson
✨ All skill levels welcome
✨ Gorgeous Yamaha U3 waiting in the window
✨ Good vibes + live energy

Come play, sing, or just hang — Let’s turn Saturday afternoon into a living room jam 💛

Start your Saturday night with Grey Swans (@greyswansmusic) — a Toronto indie-folk duo featuring singer-songwriters Katey Morley and Steve York.

⏰ DOORS: 6:30 PM


🎟 $20 ATD / PWYC


✨ SATURDAY NIGHT AT THE PAINTED LADY ✨

Cold drinks, hot music, bartop magic, and a little late-night mischief. Come get into trouble with us. 🍸💋

10pm | $10

EVERY SUNDAY • 7PM–9PM
NO COVER

Warm up for Sunday karaoke with Jukebox Jordo, a dynamic local one-man-band bringing live looping, percussion, and spontaneous energy to The Painted Lady every week.

Thanksgiving Long Weekend at The Painted Lady 🍂✨

No work Monday means Sunday night is officially fair game.

Come spend the long weekend with us for drinks, music, dancing and all the usual Painted Lady chaos — because one more night out is basically what long weekends are for.

See you at the Lady. 💋

🎤 NO REGRETS. JUST KARAOKE. ✨

Big songs, questionable dance moves, unexpected duets and absolutely NO shame. Grab the mic, channel your inner superstar and sing your heart out at The Lady.

Talent optional. Enthusiasm mandatory. 🍸💋

10PM till LATE | FREE EVENT

📋 Sign-up in person at 8PM (no online sign-ups)
🎶 Feature Artist Showcase 8:15–9PM
🎤 Open Mic 9PM–2AM • 2 songs per performer

Every week kicks off with a different feature artist. Want to be one? DM us on Instagram @openmicmonday.

An Evening of Songs & Stories with Mitch Szitas, Alexandra Babiak & Edward Sayers

Join Toronto-area singer-songwriters Mitch Szitas, Alexandra Babiak, and Edward Sayers for an intimate evening of acoustic music, thoughtful lyrics, and stories told through song.

7:30pm | $15

BUY TICKETS HERE

The night doesn’t end when the show wraps — it just shifts gears.

11 PM till late
@paintedladyossington

6pm-9pm

$5 Glasses of wine

A community-driven, safe-space dance party featuring local resident and guest DJs, producers from Toronto's diverse electronic music scene, visuals, and bar-top burlesque.

FREE | 9PM til LATE!

A Haunted Cabaret Soiree! Featuring Live Jazz, Performers, Games, Raffles, Dancing and more!

LE CABARET BOO! 🎟️ TICKETS BUY HERE

Brass, Boos & Burlesque A Haunted Cabaret Soirée

The ghosts are back, the band is playing, and the Night Circus is opening its doors for one wickedly whimsical night of Brass, Boos & Burlesque.

Step into Le Cabaret Boo!, a haunted cabaret soirée at The Painted Lady where vintage glamour meets Halloween mischief.

Expect an evening packed with:

🎺 LIVE JAZZ
The Frank Adriano Quartet, our live 4-piece jazz band, bringing the brass and keeping the party moving.

💋 BURLESQUE, DRAG & CABARET
A wicked lineup of burlesque, drag, cabaret, variety and vaudeville performers, including our notorious bar-top performances.

🥂 SHOWGIRL SHOTS
Get your shot poured straight into your mouth by our cast. You’ve been warned.

🎭 INTERACTIVE PERFORMANCES
The audience isn't just watching. Our performers will be weaving through the room and bringing the cabaret right to you.

🎟️ GAMES, RAFFLES & PRIZES
Test your luck and join in on our games and raffles throughout the night.

🔐 HIDDEN RIDDLES & MYSTERIES
Keep your eyes open. We always hide riddles, puzzles and secret clues throughout the evening. Solve them correctly and you could walk away with a prize.

💃 DANCE WITH THE BAND
Once the cabaret gets rolling, clear some space and dance the night away to live jazz.

👻 COSTUME CONTEST
Come dressed to impress, terrify, enchant or cause a little trouble. Our costume contest will crown the evening's most unforgettable creature.

🎟️ TICKETS BUY HERE

🎟️ Advance General Admission — $30

Bar stool or standing room. Seating is first come, first served.

🥂 Advance VIP — $45

Includes:

• Reserved table seating

• After-show photo opportunity with the cast

• Professional photographer portrait

🎟️ Regular General Admission — $40

🥂 Regular VIP — $55

Advance tickets are the best deal!

Last year's Le Cabaret Boo! was packed, so don't wait until the night of the show. Grab your advance ticket early and save your spot in the Circusus

Doors: 8:00 PM
Pre-show: 8:30 PM
Show: 9:00 PM

Join us at 10PM for bartop burlesque, DJs, dancing, and just the right amount of trouble. 🍸🔥

✨ All skill levels welcome
✨ Gorgeous Yamaha U3 waiting in the window
✨ Good vibes + live energy

3PM-5PM
FREE EVENT

Toronto’s Darryl Hannah joins prairie alt-country duo The Goddamsels for a special double bill at The Painted Lady. Expect dreamy country-tinged soundscapes, rich harmonies and a night that moves between psychedelic twang, folk, pop and modern alt-country.

Tickets: $15 Advance / $20 at the Door

BUY TICKETS HERE

🎤 NO REGRETS. JUST KARAOKE. ✨

Big songs, questionable dance moves, unexpected duets and absolutely NO shame. Grab the mic, channel your inner superstar and sing your heart out at The Lady.

Talent optional. Enthusiasm mandatory. 🍸💋

10PM till LATE | FREE EVENT

📋 Sign-up in person at 8PM (no online sign-ups)
🎶 Feature Artist Showcase 8:15–9PM
🎤 Open Mic 9PM–2AM • 2 songs per performer

Every week kicks off with a different feature artist. Want to be one? DM us on Instagram @openmicmonday.

Dive into the Big Shiny Tunes era with Big Shiny Band! Everyone's favourite 90s and 00s rock anthems - from your Discman right into your ears. Sing along, jump along, and come rock out with your top 8 Myspace friends.

$10 / PWYW

8pm-10pm

The night doesn’t end when the show wraps — it just shifts gears.

11 PM till late
@paintedladyossington

🎶 6–9PM | 🍾 $5 Glasses of wine

A community-driven, safe-space dance party featuring local resident and guest DJs, producers from Toronto's diverse electronic music scene, visuals, and bar-top burlesque.

FREE | 9PM til LATE!

Scone Age Thursday hits The Painted Lady this month with T—raw rock ’n’ roll, experimental energy, and local Toronto heat.

Featuring:Ok Ok, Rat Quartet, The Brghlights

Doors 9:30PM • Music 10PM • $10

Join us at 10PM for bartop burlesque, DJs, dancing, and just the right amount of trouble. 🍸🔥

SATURDAY PIANO JAM

Every Saturday

3PM–5PM • No cover

All skill levels welcome.

Saturdays were made for piano music, cold drinks and hiding out at The Painted Lady. Two easygoing hours of songs, singers, surprises and whatever little bit of magic happens to wander through the front window. Our beautiful Yamaha U3 is waiting, so if you’ve got a song in your fingers, come play. Featuring a rotating crew of guest hosts

EVERY SUNDAY • 7PM–9PM
NO COVER

Warm up for Sunday karaoke with Jukebox Jordo, a dynamic local one-man-band bringing live looping, percussion, and spontaneous energy to The Painted Lady every week.

📋 Sign-up in person at 8PM (no online sign-ups)
🎶 Feature Artist Showcase 8:15–9PM
🎤 Open Mic 9PM–2AM • 2 songs per performer

Every week kicks off with a different feature artist. Want to be one? DM us on Instagram @openmicmonday.

The night doesn’t end when the show wraps — it just shifts gears.

11 PM till late
@paintedladyossington

HAPPY HOUR PIANO JAM - live music 6pm-9pm happy people, special drink prices and Rory Lavelle bringing his piano-pop for a precarious world. Cheers.

A community-driven, safe-space dance party featuring local resident and guest DJs, producers from Toronto's diverse electronic music scene, visuals, and bar-top burlesque.

FREE | 9PM til LATE!

Sexy costume, dance party, & opera cabaret. Featuring over 10 different Halloween themed acts by an amazingly talented cast and crew 😍•  🎉🥳DOORS 7:30pm SHOW START: 8pm•

Join a band of ghouls for a night of classic tunes and good company!

Instead of staying home, scared of 👻 on Hallow's Eve, join us and our band of ghouls for a night of classic tunes and good company!

Emma Hewson, Danny Zaidman, MIP and Steve Farrugia will trick or treat you to songs such as: Thriller, Ghostbusters, The Addams Family, Highway to Hell and more!

Dress up if you dare (we will be!) and enjoy a drink with some devilishly good looking musicians!

Doors at 6:30pm, music from 7pm-9pm, $15 at the door or in advance

Buy Tickets HERE

✨ All skill levels welcome
✨ Gorgeous Yamaha U3 waiting in the window
✨ Good vibes + live energy

3PM-5PM
FREE EVENT

📋 Sign-up in person at 8PM (no online sign-ups)
🎶 Feature Artist Showcase 8:15–9PM
🎤 Open Mic 9PM–2AM • 2 songs per performer

Every week kicks off with a different feature artist. Want to be one? DM us on Instagram @openmicmonday.

Happy Hour hits different with a piano. 🎹🍷☀️

$5 glasses of wine. Piano requests. Evening hangs.

Grab a seat, throw in your favourite request and let us soundtrack your happy hour at The Lady.

Come early. Stay later than planned. ✨

A community-driven, safe-space dance party featuring local resident and guest DJs, producers from Toronto's diverse electronic music scene, visuals, and bar-top burlesque.

FREE | 9PM til LATE!

Emo Night Painted Lady! Playing all the hits from your favorite bands during your Warped Tour days!

Grab your tickets for Toronto's premier pop punk and emo tribute band, Eyes Like Static.

Dust off your skinny jeans, throw on those vans and come out to Emo Night! If you're a fan of pop punk and emo covers this event is for you!

With over 2 hours of live music from Eyes Like Static, playing hits from bands such as Blink 182, Green Day, My Chemical Romance, Paramore, Jimmy Eat World, Sum 41, Foo Fighters and so much more, you won't want to miss this event!

EARLY SHOW

$10 ADV | $15 ATD

BUY TICKETS HERE

📋 Sign-up in person at 8PM (no online sign-ups)
🎶 Feature Artist Showcase 8:15–9PM
🎤 Open Mic 9PM–2AM • 2 songs per performer

Every week kicks off with a different feature artist. Want to be one? DM us on Instagram @openmicmonday.

6pm-9pm

$5 Glasses of wine

A community-driven, safe-space dance party featuring local resident and guest DJs, producers from Toronto's diverse electronic music scene, visuals, and bar-top burlesque.

FREE | 9PM til LATE!

📋 Sign-up in person at 8PM (no online sign-ups)
🎶 Feature Artist Showcase 8:15–9PM
🎤 Open Mic 9PM–2AM • 2 songs per performer

Every week kicks off with a different feature artist. Want to be one? DM us on Instagram @openmicmonday.

🎶 6–9PM | 🍾 $5 Glasses of wine

A community-driven, safe-space dance party featuring local resident and guest DJs, producers from Toronto's diverse electronic music scene, visuals, and bar-top burlesque.

FREE | 9PM til LATE!

Toronto's Jazz Cabaret Party

Le Cabaret Bleu isn't just a show—it's a night out.

For one evening, The Painted Lady transforms into a vintage cabaret where the band is always playing, performers are everywhere, and the audience becomes part of the atmosphere. Arrive early for live jazz, grab a cocktail, and settle in before the curtain rises. During intermission, after the finale, and in between the unexpected, the dance floor is yours.

Whether you're coming with friends, celebrating a special occasion, or looking for something completely different, expect a lively room full of music, movement, and mischief.

Come celebrate the release of Emily Mac’s debut EP “ROCK N ROLL ANIMAL” a
raw, raunchy & rebellious collection of songs that echo back to classic rock with modern feminist edge. Wear your wildest rock n roll outfit: animal print, leather,
lace, red lips, fishnets anything that makes you feel like a sexy badass going to a
glam rock party! Canadian alt-rock artist Nix Ironstone will be opening the show
and Emily Mac will be performing songs from her EP live in concert. This will be a
night of powerful female fronted rock music that is bound to make you feel
powerful and rebellious!

6:30pm

$20 ADV | $25 ATD

BUY TICKETS HERE

📋 Sign-up in person at 8PM (no online sign-ups)
🎶 Feature Artist Showcase 8:15–9PM
🎤 Open Mic 9PM–2AM • 2 songs per performer

Every week kicks off with a different feature artist. Want to be one? DM us on Instagram @openmicmonday.

HAPPY HOUR PIANO JAM - live music 6pm-9pm happy people, special drink prices and Rory Lavelle bringing his piano-pop for a precarious world. Cheers.

A community-driven, safe-space dance party featuring local resident and guest DJs, producers from Toronto's diverse electronic music scene, visuals, and bar-top burlesque.

FREE | 9PM til LATE!

The underground is back. Step away from the noise and experience unseen talent from across the GTA as upcoming artists bring fresh sounds, blending alt-rock and hip-hop with a brand-new spin. Escape the night and catch the wave at The Painted Lady.

6:30pm | $15

BUY TICKETS HERE

📋 Sign-up in person at 8PM (no online sign-ups)
🎶 Feature Artist Showcase 8:15–9PM
🎤 Open Mic 9PM–2AM • 2 songs per performer

Every week kicks off with a different feature artist. Want to be one? DM us on Instagram @openmicmonday.

Happy Hour hits different with a piano. 🎹🍷☀️

$5 glasses of wine. Piano requests. Evening hangs.

Grab a seat, throw in your favourite request and let us soundtrack your happy hour at The Lady.

Come early. Stay later than planned. ✨

A community-driven, safe-space dance party featuring local resident and guest DJs, producers from Toronto's diverse electronic music scene, visuals, and bar-top burlesque.

FREE | 9PM til LATE!

📋 Sign-up in person at 8PM (no online sign-ups)
🎶 Feature Artist Showcase 8:15–9PM
🎤 Open Mic 9PM–2AM • 2 songs per performer

Every week kicks off with a different feature artist. Want to be one? DM us on Instagram @openmicmonday.

6pm-9pm

$5 Glasses of wine

A community-driven, safe-space dance party featuring local resident and guest DJs, producers from Toronto's diverse electronic music scene, visuals, and bar-top burlesque.

FREE | 9PM til LATE!

📋 Sign-up in person at 8PM (no online sign-ups)
🎶 Feature Artist Showcase 8:15–9PM
🎤 Open Mic 9PM–2AM • 2 songs per performer

Every week kicks off with a different feature artist. Want to be one? DM us on Instagram @openmicmonday.

🎶 6–9PM | 🍾 $5 Glasses of wine

A community-driven, safe-space dance party featuring local resident and guest DJs, producers from Toronto's diverse electronic music scene, visuals, and bar-top burlesque.

FREE | 9PM til LATE!

📋 Sign-up in person at 8PM (no online sign-ups)
🎶 Feature Artist Showcase 8:15–9PM
🎤 Open Mic 9PM–2AM • 2 songs per performer

Every week kicks off with a different feature artist. Want to be one? DM us on Instagram @openmicmonday.

HAPPY HOUR PIANO JAM - live music 6pm-9pm happy people, special drink prices and Rory Lavelle bringing his piano-pop for a precarious world. Cheers.

A community-driven, safe-space dance party featuring local resident and guest DJs, producers from Toronto's diverse electronic music scene, visuals, and bar-top burlesque.

FREE | 9PM til LATE!

🎄 The Lady is Closed for Christmas! 🎄

We’re taking a little holiday break to eat, drink and be merry. Wishing you all a wonderful Christmas filled with love, laughter and a little rock ’n’ roll. ❤️

See you soon! ✨

📋 Sign-up in person at 8PM (no online sign-ups)
🎶 Feature Artist Showcase 8:15–9PM
🎤 Open Mic 9PM–2AM • 2 songs per performer

Every week kicks off with a different feature artist. Want to be one? DM us on Instagram @openmicmonday.

Happy Hour hits different with a piano. 🎹🍷☀️

$5 glasses of wine. Piano requests. Evening hangs.

Grab a seat, throw in your favourite request and let us soundtrack your happy hour at The Lady.

Come early. Stay later than planned. ✨

A community-driven, safe-space dance party featuring local resident and guest DJs, producers from Toronto's diverse electronic music scene, visuals, and bar-top burlesque.

FREE | 9PM til LATE!