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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.

Dear Ms. Kitt

PAST EVENT: From Wed, Aug. 20 – Sun, Aug. 24, 2025: Hard-Bitten Productions presents the Canadian premiere of Chantel Winters’ play Dear Ms. Kitt. A powerful and tender family drama about guilt, identity and accountability, held together with a little girl’s love of Eartha Kitt. Running at Native Earth's Aki Studio. For audiences 16+.

Guild Festival Theatre 2025 Summer Season

PAST EVENT: From Thu, Jul. 10 to Sun, Aug. 24, 2025: Guild Festival Theatre’s 2025 summer season features a world premiere inspired by Shakespeare's Hamlet and a tour-de-force comedy spy thriller based on a Hitchcock classic, as well as the fourth edition of their popular Family Fest. Plus, an exciting season launch on Thursday, July 3, featuring Aqua’s Red Rhythm & Blues group!

Summer in the Park

PAST EVENT: From Fri, Aug. 22 – Sun, Aug. 24, 2025: Crossroads Theatre presents Summer in the Park – three days of live music, dance, circus, spoken word, community parties & more on the theme of 'Resilience' at Weston’s Little Avenue Memorial Park. Free and family-friendly.

Toronto’s First Post Office: Pop-up Paper Fair 2025

PAST EVENT: For two Saturdays this summer – Jul. 12 & Aug. 9, 2025: Join Toronto’s First Post Office & the Town of York Historical Society for their summer pop-up paper fair. Come out & meet the vendors, including Young W (July 12), & browse a fantastic selection of whimsical & fun cards, notebooks, stickers, pins, patches, prints, keychains & more – there's something for everyone! Free admission, for all ages.

Little Deaths Salon

PAST EVENT: One night only – Thu, Jul. 17, 2025: Kaleigh Trace and Christa Couture present the third edition of the Little Deaths Salon, a quarterly literary & performance series that explores the awe inspired by humans’ most intimate experiences: sex and death. Presented at It's Ok* Studios. All are welcome. For audiences 19+.

TOFringe: Stealing Home

PAST EVENT: From Fri, Jul. 4 – Sun, Jul. 13, 2025: Spangle Theatre presents Stealing Home at the 2025 Toronto Fringe Festival. A comedy set in a fictional Toronto neighbourhood, it pokes fun – and throws more than a little shade – at people who live in an affluent part of the city and their NIMBYism toward a proposed supportive housing project in their neighbourhood. Running on the Alumnae Theatre Mainspace.

TOFringe: Divine Monster

PAST EVENT: From Wed, Jul. 2 – Sat, Jul. 12, 2025: Bernhardt Productions presents Divine Monster at the 2025 Toronto Fringe Festival. An encounter in a Paris cemetery between the ghost of the great French actress Sarah Bernhardt and a distraught young Canadian musician leads to a passionate debate about art, fame and success in a world now dominated by social media. Presented in Soulpepper Theatre’s RBC Finance Studio in the Distillery Historic District.

TOFringe: Me and You and the Highland Coo

PAST EVENT: From Wed, Jul. 2 – Sun, Jul. 13, 2025: Happy as a Clam Productions presents Me and You and the Highland Coo at Soulpepper’s TD Studio as part of the 2025 Toronto Fringe Festival. Experience a taste of Scotland in Toronto on a road trip adventure that reminds us to look for the light in times of darkness. For audiences 14+.

TOFringe: Jack Goes to Therapy: A (Somewhat) Romantic Comedy

PAST EVENT: From Fri, Jul. 4 – Fri, Jul. 11, 2025: Zac Williams brings his critically acclaimed solo show Jack Goes to Therapy: A (Somewhat) Romantic Comedy to the 2025 Toronto Fringe Festival. An unforgettable and loveable story of a Kindergarten teacher in therapy with a broken heart after his boyfriend leaves him for the man they had a threesome with. Running at Alumnae Theatre’s Mainspace.