218 Ossington Avenue, Toronto ON M6J2Z9 Canada

Small update from us: Meta has suspended and shut down our Instagram account, which means we’ve temporarily lost the place where we normally share our shows, our artists, our weekly happenings and all the little bits of life at The Lady.

But the shows go on. 💋

We still have something happening every night of the week : Open Mic Mondays, live music, DJs, Winesday, KINETIC, karaoke, burlesque, our regular weekly hangs, special events and a constantly changing lineup of incredible local artists.

And if you love The Painted Lady, please keep checking in, sharing our listings, telling your friends and supporting the artists who make this tiny room such a special place.

With Instagram down, every share and bit of word-of-mouth genuinely helps us right now.

Instagram may be temporarily gone, but The Lady is very much alive — and the calendar is FULL. 🍸🎶🖤

Gorrdon Lightfoot at The Painted Lady 2017

Gordon Lightfoot with Nicky (Co-Owner) 2017

SHOWS

Featured

Sep 30

September 30, 2026

Happy Hour Winesday

September 30, 2026

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. ✨

September 30, 2026

Sep 30

September 30, 2026

Kinetic: an EDM Party

September 30, 2026

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!

September 30, 2026

Oct 2

October 2, 2026

A Painted Lady Friday Night

October 2, 2026

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

October 2, 2026

the Saturday ~ HAPPY HOUR ~ Piano Jam! 3pm-5pm

Oct 3

October 3, 2026

the Saturday ~ HAPPY HOUR ~ Piano Jam! 3pm-5pm

October 3, 2026

3PM-5PM
FREE EVENT

October 3, 2026

Oct 3

October 3, 2026

Warrior Women TORONTO

October 3, 2026

We are proud to be the host venue for the Toronto concert of Warrior Women — a ground-breaking 6-city concert and empowerment series designed to amplify women’s voices and celebrate local female talent.

Proceeds are being raised for Yellow Brick House, one of Ontario’s largest providers of services to women and children escaping domestic violence and abuse.

Join the rally.

$10 | 19+ | Doors at 6:45 PM

Guest Speaker:
Jeany Crux — Vibe Raiser & Transformation Coach

Band Lineup:
The Truth Untold
“The thunder and lightning of modern rock.”

Carmen Toth
“Delicate and sensual pop rock.”

Smoking in Bed
“Fist-pumping sing-a-long punk.”

Neon Bloom
“Intense passion-driven alt-pop.”

Nerima
“Punk rock for pessimists.”

Sponsors:
Warrior Women Toronto is proudly presented by Samantha Eisen & Company and partnered with Jeannette's Voice Studio.

October 3, 2026

Oct 3

October 3, 2026

A Painted Lady Saturday Night

October 3, 2026

✨ SATURDAY NIGHT AT THE PAINTED LADY ✨

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

11:30pm | $10

October 3, 2026

Oct 4

October 4, 2026

Jukebox Jordo

October 4, 2026

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.

October 4, 2026

Oct 4

October 4, 2026

Sing-a-long w/ Svetty Karaoke 10pm-LATE

October 4, 2026

🎤 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

October 4, 2026

Oct 5

October 5, 2026

Open Mic Mondays w/Kunle

October 5, 2026

📋 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.

October 5, 2026

Oct 6

October 6, 2026

The After Show

October 6, 2026

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

11 PM till late
@paintedladyossington

October 6, 2026

Oct 7

October 7, 2026

Happy Hour Winesday

October 7, 2026

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. ✨

October 7, 2026

Oct 7

October 7, 2026

Kinetic: an EDM Party

October 7, 2026

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!

October 7, 2026

Oct 8

October 8, 2026

THE MOVEMENT : FOR THE SOUL

October 8, 2026

THE MOVEMENT : FOR THE SOUL

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

Free RSVP Entry allll night!

October 8, 2026

Oct 9

October 9, 2026

The Violet Archers

October 9, 2026

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

October 9, 2026

Oct 9

October 9, 2026

A Painted Lady Friday Night

October 9, 2026

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

October 9, 2026

Oct 10

October 10, 2026

the Saturday ~ HAPPY HOUR ~ Piano Jam! 3pm-5pm

October 10, 2026

3PM-5PM
FREE EVENT

October 10, 2026

Oct 11

October 11, 2026

Jukebox Jordo

October 11, 2026

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.

October 11, 2026

Oct 11

October 11, 2026

Sing-a-long w/ Svetty Karaoke 10pm-LATE

October 11, 2026

🎤 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

October 11, 2026

Oct 12

October 12, 2026

Open Mic Mondays w/Kunle

October 12, 2026

📋 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.

October 12, 2026

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

Oct 13

October 13, 2026

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

October 13, 2026

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

October 13, 2026

SOCIALS

sending good vibrations to all our MANY friends Everywhere…

WE ARE A 100% INDEPENDENTLY OWNED VENUE.

—> Known for Our Great Sound & Vibe. Pro Gear. Acoustically-Tuned Room. <—

SHOWCASING LIVE ORIGINAL MUSIC TO TORONTO AUDIENCES FOR MORE THAN 18 YEARS.

ARTISTS WHO HAVE PERFORMED HERE: AHI, Aysanabee, Alysha Brilla, Bob Lanois, Johnny Goood & The Triple O’s (Lady Gaga’s Backing Band), Chris Thomas King (Grammy Winning Blues/HipHop/Americana Artist from Baton Rouge), Colter Wall, Rocco DeLuca, Irish Mythen, Tom Wilson (Junkhouse), Ariana Gillis, Jeff Heisholt (The Trews, Skydiggers, Current Fantasy), Kevin Hearn & Thinbuckle (Barenaked Ladies), Elise LeGrow, Robert Scott (MIchael Buble), Great Bob Scott (Look People), Richard Underhill (Shuffle Deamons), Tim Hamel, Mike Pellerin, Mary Margaret O’Hara, Big Freedia (New Orleans ‘Bounce’ /HipHop), The Mahones, Big Rude Jake, Michael Louis Johnson & Rambunctious, Lemon Bucket Orkestra, Bredren, Spooky Reuben, Paul James Band, Lily Frost, Derek Downham, Michael Phillip Wojewoda (Barenaked Ladies, Spirit of The West, Rheostatics), Julian Taylor, Dave Wall (Bourbon Tabernacle Choir), Gene Hardy, Astrid Foster, Pierson Ross & Dopamine Dream, Al Webster (Amanda Marshall, Jeff Healey, Ian Gillian), Giampoalo Scatozza (Tom Jones, Paul Young), Maurizio Guarini (Goblin), Mark Lalama, Davide Di Renzo (Tom Chochrane), Rich Moore, Donne Roberts (Juno Winner), Nelson Sobral, Iliya Vee, Gruvoria, The Roncy Boys, Wayne Cass, Vincent Jamal, Richard Taylor Group, Brutus Begins, Jay Aymar, Al SpX, Lester McLean, Marc McLean (George Michael, Andrea Bocelli, Billy Joel), Brainfudge, Cleave Anderson (Blue Rodeo), Nichol Robertson, James Paul (Garage Baby, Alanis Morissette), Ron Sexmith, U.N. Jefferson, Evan Redsky, Marc Ganetakos (Lighthouse, Nelly Furtado, Ashley MacIsaac, Film/TV Composer), Leo Valvassori (Alannah Myles), The Manic Boys and Girls Club, Grey Swans, and have worked with Jake Gold/mgmtrust.ca (Legendary Manager of The Tragically Hip, Broken Social Scene, The Pursuit of Happiness) during OssFest, and Richard Flohil (Legendary Music Publicist)…

Two women standing behind a bar counter, smiling, with beverage takeout containers in front of them. The background features dark wood shelves with various bottles and barware.

People socializing outside a tiki-style bar with neon signs and colorful lighting.

Group of five musicians performing on stage at The Painted Lady, with guitars, a keyboard, and a violin, in a dimly lit venue.

Group of people at a social gathering, some holding drinks, with a musician playing guitar in front of the group in a dimly lit pub or bar.

Neon sign announcing a weekend dance party with the text "Friday Night" and "Saturday Night" in bright colors. Below, four black-and-white photos show people dancing, socializing, and enjoying live music with drums in a dimly lit brick-walled venue.

A dimly lit bar with people sitting at the counter and socializing. Shelves behind the bar are stocked with bottles of alcohol, and there are chandeliers hanging from the ceiling.

Bartop Burlesque.Spinning glow sticks that form a circular pattern around her hips. The bar has colorful lights, a chandelier, and people seated at the counter.

A three-person jazz band performing on stage in a dimly lit venue. The drummer is in the back, and two saxophonists are in the foreground. String lights hang from the ceiling and a brick wall is in the background.

Flyer for Community Piano Jam event on Saturdays from 3 pm to 5 pm at The Painted Lady, 218 Ossington, with a partially visible piano keyboard at the bottom.

Black and white photo of person playing piano, with hands on keys, reflection of sky and trees on the piano's surface.

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 woman with dark hair and bangs playing an acoustic guitar on stage with red curtains behind her.

People dancing and socializing in a nightclub with colorful lighting, alongside a DJ using a laptop and equipment.

'Open Mic Mondays,' hosted by the Painted Lady. Free red beans and rice on Open Mic Mondays at The Painted Lady while quantities last! Full Backline proveded. Disco ball with a bite taken out of it is also on the poster.

Event schedule for OSS Fest on July 26, 2025, at North Stage. Features performances by The Reposadists, The Rider Raiders, Nelson Sobral, Lucille & Friends, Gruvoria, Iliya Vee's Hypothesis, The Rony Boys, U.N. Jefferson, and Dopamine Dream, with a n

A group of people gathered in a dimly lit room, smiling and celebrating, with some holding drinks. The atmosphere appears festive and joyful.

Bredren Reggae. A man with a beard and a beanie hat is singing into a microphone while playing a blue electric guitar on a dark stage.

Menu for The Painted Lady featuring cocktails, beers, eats, snack attack, and drinks, with a vibrant teal wall, gold-framed pictures, and a mirror in the background.

Street scene outside a café with outdoor seating, people sitting and socializing, and a storefront with bamboo decor and mannequins, one wearing colorful clothing. Large beautiful solid mahogany bar inside. Vodka, whisky, bourbon, beer.

A glass of mojito cocktail with ice, lime, mint leaves, and a black straw on a wooden table outdoors.

People socializing at an outdoor patio with wooden dividers and a canopy. Some are seated at tables, others are standing, with urban brick buildings in the background.

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.

Framed photo of two men sitting together, one with long blond hair and a sleeveless shirt, the other with curly black hair and sunglasses, against a colorful background.

A musical performance on stage with a female singer Elise LeGrow, a guitarist, and a drummer. The stage has a sign that reads 'The Painted Lady' and red curtains.

Musicians performing live on stage at The Painted Lady venue. The main musician plays an electric guitar and is in front, with a second musician playing a bass guitar behind them. Stage lighting and a sign with the venue's name are visible.

Backlit bar shelf with various bottles of liquor, beer bottles, and draft taps, set against exposed brick wall.

A glass of beer and a cocktail on a dark mahogany bar counter with colorful blurred lights in the background

Crowd dancing in a nightclub with colorful lights, chandeliers, and decorative string lights.

Two young men playing electric guitars on stage with a drummer behind them, in a dimly lit venue decorated with string lights and a disco ball.

A close-up of a drum set with a glittery blue drumhead in a dimly lit bar or club, with blurred figures of musicians and audience in the background, illuminated by warm, colorful lights.

A man playing an acoustic guitar on stage at a venue called The Painted Lady, with red curtains and a sign in the background.

Sidewalk front summer patio view of a live music bar with outdoor seating, including people dining and a chalkboard sign outside that reads 'Back Patio Vacation Vibes Open.'

A woman at a dimly lit bar with red and green lighting, surrounded by bottles of alcohol and bar equipment.

A woman bartending behind a bar with liquor bottles, with dim lighting and warm ambiance at a nightclub or bar.

A woman in lingerie dancing on stage in a dimly lit nightclub with chandeliers and colorful lights. Burlesque. EDM. Rock'n'Roll. Funk. Disco. Dance. House. Hip Hop. Afrobeat. Jazz. Blues. Dating. Live Music.. Piano Bar.

Crowded bar or nightclub with dim lighting, chandeliers, and framed pictures on the wall, with people gathered around tables and a stage area in the background. Burlesque. EDM. Rock'n'Roll. Funk. Disco. Dance. House. Hip Hop. Afrobeat. Jazz. Blues.

A band performing on stage at a venue called The Painted Lady, with four members: a guitarist with tattoos playing an electric guitar, a vocalist with a painted guitar and a bandana, and two bass players in black shirts, one with a beard and short ha

A group of four people performing live music in a dimly lit venue with colorful string lights overhead. One person is playing guitar, another is playing keyboard, and two are singing into microphones.

Two women in glamorous outfits are sitting at a table outside a building, enjoying pizza, while a man leans over the table smiling at them. Burlesque. EDM. Rock'n'Roll. Funk. Disco. Dance. House. Hip Hop. Afrobeat. Jazz. Blues. Dating. Live Music.

Two women sitting outside a tropical-themed juice bar, smiling and holding spoons, with signs advertising organic juice and smoothies behind them.

Three female musicians performing on stage: one with an accordion and microphone, another with a ukulele and microphone, and the third with an electric guitar and microphone. They are in a music venue with a sign behind them reading "The Painted Lady

Backlit bar shelf with bottles of alcohol, beer bottles, and a beer tap system in a dimly lit bar.

A woman with dark hair, red lipstick, and a big smile sitting on a bar counter in a dimly lit bar or nightclub. She is wearing a bikini top, with her legs extended across the bar. The background shows colorful, blurred lights and patrons. Burlesque.

A woman with blonde hair is playing a black grand piano while singing into a microphone. She is wearing a black lace dress and is seated on a upholstered bench. There are large green leaves behind her. Overlaid text promotes a community piano jam eve

Three men standing together with arms around each other inside a performance venue with a sign that reads "The Painted Lady" in the background. The man in the middle wears a black hat and black shirt, the man on the left has glasses hanging from his

A woman in a purple dress dancing on stage at a nightclub with a striped performer and audience watching.

A group of five people sitting inside a vintage-style booth with dark curtains and yellow trim. The woman in the center has curly blonde hair and is wearing a black outfit with a large red flower on her chest. She is wearing black tights and sneakers

Poster for a blues and burlesque event titled "Le Cabaret Bleu" featuring a woman in vintage burlesque costume holding a microphone, with text indicating live performances, prizes, games, and more, scheduled for December 11th at The Painted Lady.

Crowd of people dancing and enjoying themselves at a lively bar and club called The Painted Lady in Toronto on Ossington Avenue, with colorful artwork on the walls and chandeliers hanging from the ceiling.