Toronto, ON Toronto, ON

A Black Art Fair 2025

PAST EVENT: Two days only - Sat, Oct. 25 & Sun, Oct. 26, 2025: The Nia Centre for the Arts presents the third edition of their annual Black Art Fair. This time, it’s going to be bigger than ever, showcasing 30+ Black Canadian artists from all career stages from across the country – connecting artists with collectors, curators & art lovers nationwide.

The Veil

PAST EVENT: Extended to Sun, Oct. 19, 2025!Inspired by classic horror writers like Edgar Allan Poe and Shirley Jackson, this haunting new work tells the tale of a high-powered lawyer who inherits a sinister curse. Thought For Food Productions, in association with Crow's Theatre and Guild Festival Theatre, presents the world premiere of The Veil at Crow’s Theatre.

Spotlight at The Second City: October

PAST EVENT: Tue, Oct. 14 & Wed, Oct. 15, 2025: Toronto Sketch Comedy & The Second City Toronto present the October edition of Spotlight at The Second City, featuring $20 Sandwich and Sarah Bennett, at The Second City’s Theatre ‘73. For adults 18+.

Romeo Pimp by Jesse McQueen

PAST EVENT: From Wed, Sep. 17 – Sun, Oct. 5, 2025: The King Black Box, in partnership with One East Productions, presents the world premiere of Jesse McQueen’s play Romeo Pimp. A high school senior’s life transforms when she falls in love for the first time – but as her world expands, so does the distance between the life she’s always known and the life she's being pulled into. Charity preview presentation on Sun, Sep. 14. Audience discretion advised; ages 16+.

BEATS-BREATH: Nagata Shachu & Jiro Murayama

PAST EVENT: One night only - Sat, Oct. 4, 2025: Taiko ensemble Nagata Shachu kicks off their 28th season with BEATS-BREATH, an exciting collaborative concert with shinobue (bamboo flute) master Jiro Murayama at The Fleck at Harbourfront Centre Theatre. Together, they’ll perform new compositions and traditional Japanese folk festival pieces.

The Green Line

PAST EVENT: From Fri, Sep. 19 – Sat, Oct. 4, 2025: Buddies in Bad Times Theatre opens their 47th season with the Toronto premiere of award-winning Canadian play The Green Line, by Makram Ayache. Two love stories twist together in two Beiruts riven by time & conflict. Produced by In Arms Theatre Company & the MENA Collective, in association with Buddies in Bad Times Theatre & Factory Theatre. For audiences 19+.

Colonial Circus

PAST EVENT: Tue, Sep. 23 – Sun, Sep. 28, 2025: Two2Mango brings their award-winning clown show Colonial Circus to Toronto, running at Native Earth’s Aki Studio. Through bouffon, song, dance, audience interaction, gestures and morphing props, two Brown clowns give a hilarious, unforgettable lesson on the history of colonization. For audiences 16+. 

What The Festival 2025

PAST EVENT: Three days only – from Thu, Sep. 25 – Sat, Sep. 27, 2025: Strange Maker Collective presents their second annual What The Festival, an active celebration of all things drag, clown and puppetry. Toronto's wildest live theatre festival features eyebrow-raising spectacles, theatre and cabaret performances, plus a balloon workshop and a panel on clown and bouffon. Weird & wonderful - they have it all! Happening in spaces at Youngplace. For audiences 18+.

The Second City Toronto presents: Sam Sferrazza records a comedy album

PAST EVENT: One night only - Sat, Sep. 6, 2025: The Second City Toronto presents stand-up comedian Sam Sferrazza, recording a live comedy album during two performances at the John Candy Box Theatre with opening act Ben Sosa Wright. Come out and be a part of the studio audience and have your laughter immortalized forever! For adults 18+. 

Spotlight at The Second City

PAST EVENT: Tue, Sep. 2 & Wed, Sep. 3, 2025 + one Tue & Wed every month until the end of 2025: Toronto Sketch Comedy & The Second City Toronto present Spotlight at The Second City, a new monthly series presenting sketch comedy’s best troupes. September’s line-up features award-winning Potato Potato & Small Friend Tall Friend – on at The Second City’s Theatre ’73. For adults 18+.

Toronto Outdoor Picture Show 2025

PAST EVENT: From Thu, Jun. 12 – Sun, Aug. 24, 2025: Toronto Outdoor Picture Show (TOPS) presents their 15th anniversary festival of open-air cinema programming. Screenings take place over 20 evenings throughout the summer at three parks across Toronto: Fort York, Christie Pits and Corktown Common. This year’s theme is When We Were Young – a throwback to their inaugural programme, featuring beloved coming-of-age films.