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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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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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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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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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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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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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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Jukebox Jordo Patio Party
Aug
16

Jukebox Jordo Patio Party

Jukebox Jordo is a dynamic local one-man band bringing the patio to life with live looping, percussion, and spontaneous feel-good energy.

Expect playful grooves, good vibes, and a Sunday night that feels fresh, fun, and fully alive.

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Wytchfae + Second Wife
Aug
13

Wytchfae + Second Wife

On the thirteenth night of the eighth month of Year of the crow (2026), will gather music lovers of the most radical sort. Second Wife and Wytchfae join forces to bring super fun vibes to the long fabled Painted Lady.
8:00pm

$15 ADV | $20 ATD TICKETS HERE

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Sexy Trivia
Aug
11

Sexy Trivia

Spice up your week with a competition full of cheeky questions and surprising facts, with sexy prizes for the winners who know the most! Grab your team or come solo and test your knowledge of bodies, pleasure, and everything in between. Get ready to brag when you win our amazing spicy prizes.

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Jukebox Jordo Patio Party
Aug
9

Jukebox Jordo Patio Party

Jukebox Jordo is a dynamic local one-man band bringing the patio to life with live looping, percussion, and spontaneous feel-good energy.

Expect playful grooves, good vibes, and a Sunday night that feels fresh, fun, and fully alive.

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​Rich Freed & The Renegades and Holden Grey
Aug
8

​Rich Freed & The Renegades and Holden Grey

Join us at The Painted Lady on Saturday, August 8th, for an incredible co-headlining night featuring two of Toronto's most dynamic live acts!

Rich Freed & The Renegades bring a powerhouse blend of heavy indie rock, funk grooves, and soulful folk and blues elements. Born in Glasgow and now a prominent voice on Toronto's stages, singer-songwriter Rich Freed fronts a remarkably tight, high-energy band. Expanding his sonic landscape with drums, bass, lead guitar and backing vox, The Renegades add a massive, electric performance built to get a room moving.  

​Holden Grey is a psychedelic and folk-rock band led by Erich Braunsteiner. Drawing inspiration from '60s classics all the way through to modern '10s neo-psychedelia, they create a captivating, immersive soundscape. The band is currently celebrating their massive debut release, Daydream/Nightmare, a 28-song concept double album that showcases their signature blend of sweet psychedelic rock goodness.

​Don't miss this stellar lineup of local talent sharing the stage for one night only.

​Doors: 6:30 PM

​Tickets: $15

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Ani Mari and North Ingalls EAST COAST TOUR
Aug
7

Ani Mari and North Ingalls EAST COAST TOUR

Join two Michigan-based artists, North Ingalls and Ani Mari, for a night of indie folk and indie rock original songwriting! This is Ani Mari's second time playing at The Painted Lady, and she's so excited to return to Toronto with her friends from Ann Arbor.

6:30pm | $15

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