HAPPY HOURS till 8pm!
HAPPY HOURS! Special pricing just for being you. 6pm-8pm Talk to our Bartenders for details. Cheers.
Open Mic Mondays w/Kunle
📋 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 HOURS till 8pm!
HAPPY HOURS! 6pm-8pm
Great bartenders who truly care about the drinks they make & serve. 14 draught taps. Artisanal coktails. Kick off your night the right way… Cheers.
The After Show
The night doesn’t end when the show wraps — it just shifts gears.
11 PM till late
@paintedladyossington
WINESDAY Happy Hour live sing-a-long piano w/ Heidi Savoie
🎶 6–9PM | 🍾 $5 Glasses of wine
Back To Where It All Started ...Manic Boys and Girls Club with Jennifer Bettencourt
The Manic Boys and Girls Club return to where it all began.Back at the very first venue to ever book them, The Painted Lady, for one night only.
9 PM | $15
Joining them is special guest Jennifer Bettencourt
And in true throwback fashion — this is a physical ticket event. Hard copy tickets will be mailed and required for entry. No downloads. No QR codes. Just a real concert ticket in your hand.
HAPPY HOURS till 10pm!
HAPPY HOURS! Special pricing just for being you. 6pm-10pm Talk to our Bartenders for details. Cheers.
Rodolfo Roger & The Acoustic Hearts ft Leo Franco & Burçin
Rodolfo returns to the stage at The Painted Lady on May 29 with his unplugged trio, Acoustic Hearts. Blending stripped-down originals with reimagined covers
6:30pm | $12 ADV / $16 ATD
HAPPY HOURS till 10pm
HAPPY HOURS! Special pricing just for being you.
3pm-10pm Talk to our Bartenders for details.
Cheers.
A Painted Lady Saturday Night
🍸 Drinks flowing
🎶 Music loud
💃 No early exits
If you’re still standing, you’re doing it right.
See you at The Lady.
🪩10PM TIL LATE
Open Mic Mondays w/Kunle
📋 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 After Show
The night doesn’t end when the show wraps — it just shifts gears.
11 PM till late
@paintedladyossington
WINESDAY Happy Hour piano sing-a-long with Meher Steinberg till 9pm
6pm-9pm
$5 Glasses of wine
Eyes Like Static
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!
9PM | $10 ADV | $15 ATD
Sunday Country Roundup
Sunday Country Roundup'.
good energy Sunday patio set featuring a mix of well-known country covers and original songs.
2:30pm-5:00pm
PWYW
Open Mic Mondays w/Kunle
📋 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 After Show
The night doesn’t end when the show wraps — it just shifts gears.
11 PM till late
@paintedladyossington
Happy Hour Piano Jam
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.
NXNE
7 PM - Doors
8 PM: Casey Garcia
9 PM: Skystar
10 PM: Jaghuligin
11 PM: Vile Murk
12 AM: Sixxera
Sunday Country Roundup
Sunday Country Roundup'.
good energy Sunday patio set featuring a mix of well-known country covers and original songs.
2:30pm-5:00pm
PWYW
Open Mic Mondays w/Kunle
📋 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 After Show
The night doesn’t end when the show wraps — it just shifts gears.
11 PM till late
@paintedladyossington
Under the Covers and Second Hand Trio
DON'T JUDGE A BOOK BY ITS COVER
Rock takes over The Painted Lady on June 19th. Expect a high-energy mix of well-known classics and hard-hitting rock anthems.
➡️Doors: @ 06:30
UNDER THE COVERS: 7 pm
SECOND HAND TRIO: 8 pm
$10 BUY TICKETS HERE
See you on the dance floor !
Sunday Country Roundup
Sunday Country Roundup'.
good energy Sunday patio set featuring a mix of well-known country covers and original songs.
2:30pm-5:00pm
PWYW
Open Mic Mondays w/Kunle
📋 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 After Show
The night doesn’t end when the show wraps — it just shifts gears.
11 PM till late
@paintedladyossington
WINESDAY Happy Hour piano sing-a-long with Donavon LeNabat till 9pm
6pm-9pm
$5 Glasses of wine
Saturday Piano Jam 3pm-5pm
✨ All skill levels welcome
✨ Gorgeous Yamaha U3 waiting in the window
✨ Good vibes + live energy
3PM-5PM
FREE EVENT
Open Mic Mondays w/Kunle
📋 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 After Show
The night doesn’t end when the show wraps — it just shifts gears.
11 PM till late
@paintedladyossington
Open Mic Mondays w/Kunle
📋 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
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.
Open Mic Mondays w/Kunle
📋 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.
WINESDAY Happy Hour live sing-a-long piano w/ Heidi Savoie
🎶 6–9PM | 🍾 $5 Glasses of wine
Makenzy Williamson Album Release
Makenzy Williamson brings her powerful alt/rock sound to Toronto this July for the release of her debut 12-track album!
7:00pm | $15
Open Mic Mondays w/Kunle
📋 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.
WINESDAY Happy Hour piano sing-a-long with Donavon LeNabat till 9pm
6pm-9pm
$5 Glasses of wine
B R O T H E R L E E D S , NEWPORT ELECTRIC, RYAN NAISMITH BAND
B R O T H E R L E E D S , NEWPORT ELECTRIC, RYAN NAISMITH BAND
Three original bands, four cities, 1000 Kilometers.
9pm/$10
Saturday Piano Jam 3pm-5pm
✨ All skill levels welcome
✨ Gorgeous Yamaha U3 waiting in the window
✨ Good vibes + live energy
3PM-5PM
FREE EVENT
Open Mic Mondays w/Kunle
📋 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 HOURS 1pm-6pm
HAPPY HOURS ! Drinks Specials just for being you. 1pm-6pm Talk to our bartenders for details. Psychological counseling is free. Cheers
Back To My Roots
Back To My Roots is a Nashville-style writers round where the artists share their songs & the stories behind them
1:00pm | $10 ADV / $15 ATD
A Painted Lady Saturday Night
🍸 Drinks flowing
🎶 Music loud
💃 No early exits
If you’re still standing, you’re doing it right.
See you at The Lady.
🪩10PM TIL LATE
HAPPY HOURS TIL 10PM
HAPPY HOURS! Special pricing just for being you. 6pm-10pm Talk to our Bartenders for details. Cheers.
THE Saturday ~HAPPY HOURS~ Piano Jam! 3pm-5pm
✨ All skill levels welcome
✨ Gorgeous Yamaha U3 waiting in the window
✨ Good vibes + live energy
3PM-5PM
FREE EVENT
Social Credentials
Come celebrate with your favourite band you didn't know about! Bring your favourite dancing shoes!
6:30pm | $15
HAPPY HOURS till 10pm!
HAPPY HOURS! 6pm-10pm
A fun hang with friendly, fun locals & great music spinning. Cheers.
High School Crush
From iconic anthems to forgotten favourites, this cover band brings pure millennial nostalgia.
Doors 830pm
Music 9pm - late.
$5 Entry
HAPPY HOURS 6PM-8:30 PM
HAPPY HOURS! Great music spinning & drink specials all night long ~ just because it’s Thursday. 6pm-8pm Cheers
WINESDAY Happy Hour piano sing-a-long with Donavon LeNabat till 9pm
6pm-9pm
$5 Glasses of wine
The After Show
The night doesn’t end when the show wraps — it just shifts gears.
11 PM till late
@paintedladyossington
The Kimora Show: A BurlesquE & Music variety show 7:30pm
The Kimora Show: Back by popular demand. Showcasing local TO burlesque talent, and a Tuesday night party for all our friends & fans. Exciting raffle prizes, limbo contest, and more!
7:30pm | $15 Cash only
Open Mic Mondays w/Kunle
📋 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 HOURS till 8pm!
HAPPY HOURS! Special pricing just for being you. 6pm-8pm Talk to our Bartenders for details. Cheers.
LONG WEEKEND SUNDAY! Dance Party, Bartop burlesque & happy hours all night long!
Long Weekend Sunday! Let’s GO! 10PM | $10
Let loose. Stay late. The Lady’s waiting. 🍸
LONG WEEKEND happy hours ~all day+Night sunday!
HAPPY HOURS! Special pricing just for being you. 6pm-10pm
Talk to our Bartenders for details.
Cheers.
A Painted Lady Saturday Night
10pm til Late | $10💋 Drink. Dance. Repeat. Only @ The Painted Lady 🍷
HAPPY HOURS till 10pm!
HAPPY HOURS! Special pricing just for being you.
3pm-10pm Talk to our Bartenders for details.
Cheers.
the Saturday ~happy hourS~ Piano Jam! 3pm-5pm
✨ All skill levels welcome
✨ Gorgeous Yamaha U3 waiting in the window
✨ Good vibes + live energy
3PM-5PM
FREE EVENT
Ceippo with pickpocket and hawkeye meister
come celebrate the release of ceippo's new single "fifteen ton head." supported by pickpocket and hawkeye meister, the best acts that the dirty streets of toronto have created. it will be a night of good rock music, and perhaps even better vibes
6:30pm | $10
HAPPY HOURS till 10pm!
HAPPY HOURS! Special pricing just for being you. 6pm-10pm Talk to our Bartenders for details. Cheers.
The CleanUp Crew CABARET: Clock in. Strip down. Make a mess.
This isn’t just a show—it’s a late-night, high-energy burlesque dance party where the staff take over. Housekeepers, bellhops, managers, and misfits trade in their duties for dirty secrets, seductive chaos, and pulsing music.
8:00pm | BUY TICKETS HERE
With a live DJ spinning all night, the energy builds from the moment doors open. Expect immersive performances, character-driven burlesque, and a crowd that becomes part of the atmosphere. As the night goes on, the lines blur between stage and dance floor—what starts as a reset turns into a full after-hours takeover.
HAPPY HOURS from 6pm-8pm
HAPPY HOURS! Special pricing just for being you. 6pm-8pm Talk to our Bartenders for details. Cheers.
WINESDAY Happy Hour piano sing-a-long with Meher Steinberg till 9pm
6pm-9pm
$5 Glasses of wine
The After Show
The night doesn’t end when the show wraps — it just shifts gears.
11 PM till late
@paintedladyossington