Painting The Painted Lady with Twintwa, Beaky Holden, Shbebly
Sep
5

Painting The Painted Lady with Twintwa, Beaky Holden, Shbebly

The 4th edition of Painting the Painted Lady

Featuring the signature Hypno Folk Punk Acoustigaze song craft of Twintwa

Deep growling power folk punk Prowess of Kitcheners secret weapon Beaky Holden

Syncopated cerebral live action painting of the deep genius Shbebly

Art supplies provided for audience artistic participation.

7 - 9pm | $15pwyc

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Kaythe ft. James Dunbar
Sep
8

Kaythe ft. James Dunbar

Kaythe ft. James Dunbar bring a soulful mix of R&B, jazz, indie-pop, and timeless standards to The Painted Lady.

Inspired by Ella Fitzgerald, Etta James, Amy Winehouse, and Olivia Dean, the Toronto duo blends expressive vocals, nuanced piano, fresh takes on classics, and original songs.

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The Pressures & Sad Francis
Sep
11

The Pressures & Sad Francis

A night of Toronto local grungy and post-punk alt vibes 😎 

6:30pm | $15

The Pressures are a new Toronto-based rock trio with a soft spot for the post-punk revival and alt stylings of the early 2000s. Influenced by the likes of The Strokes, The Killers, and Radiohead, the trio explores the alienation of young adulthood while putting memorable songwriting at the forefront.

Sad Francis alt/grunge/psych/shoegaze

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Grey Swans Saturdays
Sep
12

Grey Swans Saturdays

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


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Jukebox Jordo
Sep
13

Jukebox Jordo

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.

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Jukebox Jordo
Sep
20

Jukebox Jordo

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.

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Jukebox Jordo
Sep
27

Jukebox Jordo

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.

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Gio Gardener, B.L.U, and Dream V
Sep
29

Gio Gardener, B.L.U, and Dream V

Join us for an intimate, high-energy night of local alternative rock, featuring a diverse lineup of sharp songwriting, heavy textures, and raw live sound, the night brings together three distinct acts for a split-bill show you won't want to miss.

​Doors: 7:00 PM | Music: 7:30 PM

​Cover: $15 BUY TICKETS HERE

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Warrior Women TORONTO
Oct
3

Warrior Women TORONTO

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.

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The Night Circus
Oct
15

The Night Circus

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.

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The Night Circus
Nov
19

The Night Circus

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.

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Squid Mountain and People Walking By
Sep
4

Squid Mountain and People Walking By

Two long-standing Toronto rock bands take the stage for the first time in more than six years. Squid Mountain returns to performing just in time to celebrate the release of two new singles. In support, People Walking By also re-unites after a long hiatus. Prepare your mind and body for a night of evocative songwriting, soulful grooves, and the authentic energy that can only come from working-class bands giving it their all!

6:30pm | $15

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Nutmeg & The Firm
Sep
3

Nutmeg & The Firm

Nutmeg & The Firm
Thursday, September 3 | 8PM | $10 PWYW

After a month on the road across Southern Ontario, Nutmeg & The Firm return home to Toronto for a high-energy night of rock ’n’ roll at The Painted Lady.

Formed after a chance meeting at a bar in September 2025 actually turned into that rarest of things—a promise to jam that really happened—the four-piece has quickly built a reputation playing marathon sets across Ontario. Expect unreleased originals from two albums-in-the-making alongside favourites from Oasis, The Tragically Hip, Blue Rodeo, Dire Straits, Bruce Springsteen, Neil Young and more

Thursday, September 3 | 8PM | $10 PWYW

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Don Valley Drifters
Aug
28

Don Valley Drifters

The Don Valley Drifters bring high and lonesome bluegrass Featuring James Kilby, Giulio Leghissa, and Gabriel Bench, expect tight picking, heartfelt harmonies, and classic bluegrass energy from 7:00 PM–9:00 PM. PWYW

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Join Maddisun and her full band, on her "Genuine Energy Tour" featuring special guest Julie Title
Aug
27

Join Maddisun and her full band, on her "Genuine Energy Tour" featuring special guest Julie Title

Join Maddisun and her full band, on her "Genuine Energy Tour" featuring special guest Julie Title

Born in the wilderness of Cranbrook, BC, Maddisun sets off for the big city once again, with her Genuine Energy Tour. In 2026 alone Maddisun completed a 13-show tour across Ireland and the UK, a showcase at Canadian Music Week in Toronto, and over 50 live shows. Maddisun is known for her warm, magnetic presence and powerhouse vocals, she blends songwriter-folk storytelling with rootsy rock energy. Keeping you dancing, and falling in love all night.

BUY TICKETS HERE

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LE CABARET BLEU: Brass, Blues & Burlesque!
Aug
20

LE CABARET BLEU: Brass, Blues & Burlesque!

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.

⏰ Doors 8:00 PM | Live Jazz Pre-Show 8:30 PM | Show 9:00 PM

BUY TICKETS HERE

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