The Painted Lady 〰️

Est. 2007

OPEN 8 DAYS A WEEK
Fully Stocked Bar
L  I  V  E    M  U  S  I  C

A circular logo for The Painted Lady in Toronto, established in 2008, featuring a vintage pin-up style woman sitting among flowers, with text indicating offerings such as burgers, ques, live music, great food, and bar.

☕️🍸 DAILY HAPPY HOUR @ THE LADY 🍸☕️
2PM–6PM • Every. Single. Day. Sip, snack, and stay awhile — with organic coffee, craft cocktails, and high-speed internet day or night. Whether you’re working, vibing, or just unwinding, The Painted Lady’s the perfect spot to plug in or chill out. ✨

EVENTS

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EVENTS *

Featured
WINESDAY Happy Hour with Meher Steinberg
Dec 3
WINESDAY Happy Hour with Meher Steinberg
Kinetic
Dec 3
Kinetic

A not-for-profit community dance party featuring music from our local residents and Toronto's diverse electronic communities, producers and DJs each and every Wednesday.

Pop Up Holiday Market
Dec 5
Pop Up Holiday Market

9am-5pm

Henry and Monique Folk Explosion
Dec 5
Henry and Monique Folk Explosion

6:30pm | $10

The Getdown - 10PM DANCE PARTY 🎧✨
Dec 5
The Getdown - 10PM DANCE PARTY 🎧✨

10pm til late | $10
SEE YOU ON THE DANCE FLOOR

Community Piano Jam with  Windsor Johnson
Dec 6
Community Piano Jam with  Windsor Johnson

3PM-5PM
FREE EVENT

Rosa Ingenious and Penny Benjamin
Dec 6
Rosa Ingenious and Penny Benjamin

6:30pm | $10

⚡️ SATURDAYs with @djnv_to 
Dec 6
⚡️ SATURDAYs with @djnv_to 
Afterglow ft. Mont Kantapon, Joshel, A$iia
Dec 7
Afterglow ft. Mont Kantapon, Joshel, A$iia

7:00pm | $15

TICKETS HERE

Open Mic Mondays w/Kunle
Dec 8
Open Mic Mondays w/Kunle

8pm SIGN UP

Everyone Welcome!

Vegas Cabaret
Dec 9
Vegas Cabaret

7pm doors!

The After Show
Dec 9
The After Show
Happy Hour with Ori Dagan
Dec 10
Happy Hour with Ori Dagan

🎹🍷 HAPPY HOUR WINESDAY 🍷🎹
✨ Live piano. $5 glasses of wine. Pure midweek magic.

Kinetic
Dec 10
Kinetic

A not-for-profit community dance party featuring music from our local residents and Toronto's diverse electronic communities, producers and DJs each and every Wednesday.

Le Cabaret Bleu 4: Home for the Holidays
Dec 11
Le Cabaret Bleu 4: Home for the Holidays

A Live Jazz Cabaret Soirée at The Painted Lady
December 11 | Pre-show 8:30 PM | Show 9:00 PM | TICKETS HERE

SOCIALS

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SOCIALS *

View fullsize ✨ THIS WEEK AT THE LADY • DEC 1–7 ✨ 
Check back daily — new surprises & updates 👀 🎟️ Advance tickets & details on our website — link in bio
🍸 Happy Hour • Daily • 3–7PM MONDAY DEC 1
🎤 Open Mic &bull
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View fullsize Saturday November 29! 🎶 Live Music • 6:30PM — @dandelionhighway @rich_freed
View fullsize 🎹 TODAY! 3–5 PM — Community Piano Jam ✨ Hosted by @mehersteinberg ✨ 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 afternoo
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View fullsize FRIDAY NIGHT * LIVE MUSIC Cherry Garcia Band vs Danceland at The Painted Lady in Toronto!! this is going to be a fun show y’all, equal parts Grateful Dead, JGB and OGs!!! this will be our first show at The Painted Lady and we are beyond excited
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View fullsize ✨ THIS WEEK AT THE LADY • NOV 24–30 ✨ Check back daily — new surprises & updates 👀 🎟️ Advance tickets & details on our website — link in bio 🍸 Happy Hour • Daily • 3–7PM MONDAY NOV 24 🎤 Open Mic &b
View fullsize TONIGHT 💥 FREE RANGE MUSIC SERIES! Step into the vibrant heart of Toronto’s indie music scene at FREE RANGE and join us for an eclectic showcase of diverse sounds and talents. This month we feature @huntingowls @numenaband & @haydenryann
View fullsize ✨ THIS WEEK AT THE LADY • NOV 24–30 ✨ Check back daily — new surprises & updates 👀 🎟️ Advance tickets & details on our website — link in bio 🍸 Happy Hour • Daily • 3–7PM MONDAY NOV 24 🎤 Open Mic &b
View fullsize International Pop Overthrow 2025 Sunday November 23 Flash Bang
View fullsize International Pop Overthrow 2025 Sunday November 23 Violet and The Flames
View fullsize 🎤 10:00 PM till LATE — Sing•A•Long with Svetlana Konswallow Karaoke @theladykonswallow is back to turn the mic into magic. You don’t have to sing well to SLAY karaoke — just bring the chaos, the laughter, and your best (o
View fullsize International Pop Overthrow 2025 Sunday November 23 Nicky Koro @nickykoro
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View fullsize International Pop Overthrow 2025 Sunday November 23 Tara Van @taravanmusic
View fullsize International Pop Overthrow 2025 Sunday November 23 Erika Werry @eedubz
View fullsize IPO Saturday November 22 @the_discardedband

OUT AND ABOUT AT THE PAINTED LADY

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OUT AND ABOUT AT THE PAINTED LADY *

Our Community!

Two women singing into microphones on a dark stage, illuminated by colorful stage lights.
Nicky Potter with Gordon Lightfoot
A woman dressed in a feathered costume and feathered headpiece inside a dimly lit bar or nightclub, with framed artwork on a brick wall behind her and a chandelier hanging from the ceiling.
A promotional poster for an open mic night featuring a painted lady butterfly and text details including date, host, location, and sign-up time.
People dancing and socializing in a nightclub with colorful lighting, alongside a DJ using a laptop and equipment.
Kiefer Sutherland and his band
Sam with Lady Gaga's Band
Flyer for a community piano jam event with a background of a piano keyboard and sheet music. The event is open to all and takes place on Saturdays from 3 pm to 5 pm at The Painted Lady, 218 Ossington.
A detailed illustration of a red rose with green leaves and a bud, with the words 'LOVE' in the top left and 'JOIN THE REVOLUTION' in bold text at the bottom.
A woman in a bar dressed in a burlesque style costume with a large red feathered headdress, fishnet stockings, and pasties, smiling at the camera. The bar is lit with warm orange and yellow lights, with shelves of liquor bottles and a couple of peopl
Promotional poster for Grey Swans, Second Saturdays at The Painted Lady, 7-9 PM, featuring illustrated black swallows on snow-covered branches with a pink circle background and black and white trees.
A performer singing into a microphone while playing an electric guitar on stage. The performer has short hair and is wearing a sleeveless patterned top and jewelry. Behind them, a sign reads "The Painted Lady" in red and orange letters, and colorful
A black and white photo of a music performance in a dimly lit venue. There are two people on stage, one holding a guitar, with bright lights shining behind them. In the foreground, a drum set is visible.
Davide DiRenzo with Mark Lalama and Rick Moore
A person dancing on a stage with a digital backdrop that displays the word 'Kinetic' and various geometric patterns, with a DJ performing in the background.
Alysha Brilla and Lisa
Event poster for Free Range music showcase, featuring a performer on stage with a colorful costume and an audience, with the background sign reading "The Painted Lady."
Four smiling adults, three women and one man, pose closely together in a bar with colorful neon lighting, brick walls, framed pictures, and a chalkboard menu in the background.
A collage of nine black and white photos of a woman singing into a microphone, wearing a patterned dress, with colorful paint strokes and the words "sing along with Shetana Kongsawall" and "karaoke".
Two women singing and playing guitar on stage with warm orange lighting.
A black and white collage featuring five women in various poses, with the words 'BART BURETQUE' vertically aligned along the right and bottom. There is a circular logo at the bottom center reading 'FRI & SAT NIGHT' and 'The Painted Lady'.
Logo with the word 'KINETIC' and a stylized globe or sphere in the background, featuring geometric shapes and abstract lines.
Woman taking a selfie in a mirror, wearing red and black lace lingerie, with red hair and a red feathered headpiece, holding a phone in her right hand, touching her face with her left hand.
PA%2Band%2BBubba.jpg
A woman with long brown hair playing a grand piano decorated with colorful lights, singing into a microphone, in an indoor venue with neon lighting.
A woman in a red and black outfit performing a split on a stage with musical instruments in the background, neon pink lights, and a sign that reads 'Tainted Lady'.
A group of people gathered in a dimly lit room, smiling and celebrating, with some holding drinks. The atmosphere appears festive and joyful.
neon signs reading "Friday Night," "Saturday Night," and "Dance Party" with black and white photos of people dancing and playing drums at a party, and a circular logo with "The Painted Lady," "10:30 PM," and event details.
Retro-style poster advertising Soul Sunday music event with vinyl records and a skillet, promoting soulful grooves and sound sets at 218 Ossington Ave.
A woman with dark hair and bangs playing an acoustic guitar on stage with red curtains behind her.
Black and white photo of person playing piano, with hands on keys, reflection of sky and trees on the piano's surface.