The best arts and culture to enjoy when the sun sets in Toronto this month

Summer may be ending, but with the dreaded earlier sunset comes an exciting perk of living in this city — the nightlife. September is when Toronto comes alive with arts, culture, fascinating food experiences and pop-ups and plenty of other cool things to do when the sun and temperature goes down. From comedy in an alley to trending piano bars, here are the best ways to make the most of your nights this season in Toronto.

Piano bars


Jean Darlene Piano Room

Unleash your inner night owl and embark on an exhilarating adventure at the Jean Darlene Piano Room! Prepare yourself for an evening brimming with sensational live performances, ranging from soul-stirring pianists to captivating drag shows, infectious samba beats and thrilling themed singalongs at this hidden gem on Dundas Street West.


Wedlocks, a new restaurant and piano lounge in Toronto’s east end, infuses fresh energy into the historic space once occupied by Whitlocks. Owner Michelle Slota opened this dynamic venue last August, offering a dual experience of fine dining and live entertainment. Slota aims for Wedlocks’ spacious 2,300-square-foot setting to leave a lasting impression on Toronto’s jazz community.


Toronto’s piano bar trend is blazing hot, even iconic spots like the Senator have hopped on board. After nearly a century of operation, the Senator revamped its second floor into a posh piano bar, right above the bustling main dining room. The Senator, famously graced by Elton John, was reborn after a whopping 884 days of closure, thanks to the enchanting piano bar.

Arts vibes


Cry Baby Gallery

Cry Baby Gallery is a unique blend of street art and mixology. Tucked behind an art gallery, this Prohibition-style speakeasy offers impressive cocktails and a low-key vibe. Step through the gallery’s passageway and uncover a mesmerizing space where street art meets a New York–style speakeasy. Cry Baby is a hidden gem celebrating creativity and offering an unforgettable experience in Dundas West.


Kissa is a new Japanese-inspired listening lounge on King Street West. It offers Japanese cuisine, elevated cocktails and music from the ’80s to early 2000s. The venue has a vintage sound system, DJ booth, record wall, disco balls, velvet details and ambient lighting. Kissa provides a unique blend of arts, music, cuisine and cocktails for an unforgettable experience.

Friday Nights at the ROM

Courtesy ROM After Dark

Experience the ultimate late-night fun in Toronto at the Royal Ontario Museum’s Friday Nights. Get ready to party among dinosaurs as this weekly event transforms the country’s largest museum into a vibrant bash. Sip on cocktails, indulge in delicious bites from pop-up food vendors, and enjoy live music. Each event is themed around the ROM’s latest special exhibit. It’s a unique and unforgettable way to explore the museum and have a blast after hours.

Culture three ways 


Music on a boat

Experience the enchantment of R&B Under the Stars, a captivating concert series presented in partnership with Waveland. Set sail on a pirate ship across Toronto Harbour where emerging vocalists showcase their talent. With 50 events from June to September, this series is highly regarded as Canada’s top musical experience on Airbnb. 

Movies in a park

September is the perfect time to enjoy a movie outdoors! There are still a few venues running outdoor movie nights, including Downtown Yonge, with a School of Rock movie night on Sept. 6 at College Park, and the last two movie nights of the season with the Bloor West Village BIATurning Red on Sept. 1 and Dennis the Menace on Sept. 8. Kick off the school year in style! 

Comedy in an alley

This intimate Queen Street East outdoor venue offers limited seating for a cosy and enjoyable experience in, yes, an alleyway. Featuring professional headlining comedians seen on Just For Laughs, JFL42, Comedy Network, CBC, HBO and CRAVE, along with special guest openers, Comedy Alley promises a fun-filled evening with friends. Be sure to reserve your seats in advance as this popular spot tends to sell out quickly.

For more amazing things to do when the sun goes down in Toronto, click here. 

Article exclusive to STREETS OF TORONTO