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Toronto, ON Toronto, ON

Past event: Greyed out detail of a collage image containing various photos of the same man, with close-ups of skyscrapers in the background on either side. In the main central image, he has short cropped hair, light beard and moustache, and wears glasses and a suit as he gazes down, smiling at us. In the other smaller photos, he wears eye glasses, sunglasses or no eyewear as he strikes various poses in a variety of outfits - in some cases, taking a selfie.

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+. 

Past event: Greyed out image featuring yellow and white text superimposed over a blue-filtered photograph. Spotlight at The Second City. Toronto. The centre of the "O" in "Spotlight" is the silhouette of a spotlight. A view from the back of a comedy venue in an old brick building with crescent-shaped windows. Cabaret seating, with tables and chairs, facing toward the stage.

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+.

Past event: Greyed out image of a group of people sitting in a park on blankets on the grass, watching an outdoor screening of black & white movie Roman Holiday, the Toronto skyline - including the CN Tower - in the background.

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.

Past event: Greyed out illustrated poster image for Dear Ms. Kitt, the title in red handwritten font at the left against a charcoal black background. To the right: A beam of yellow light across the floor, where the black silhouette of a little girl sits in front of a microphone stand toward the top right, and the grey shadow of an adult woman holding a suitcase stretches out across the floor behind her.

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+.

Past event: Greyed out image of two play posters, featuring illustrations & yellow text, side by side. Left: The 39 Steps. Adapted by Patrick Barlow from the novel by John Buchan from the movie by Alfred Hitchcock - against a blue background. Above the text, a silhouette of a man running toward an ascending staircase, a biplane in pursuit in the cloudy sky above. Right: Heratio by Genevieve Adam on a purple background. Below the text, a white skull wearing gold crown, with a purple flower at its temple.

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!

Past event: Greyed out image featuring yellow & black text, photograph & illustration against a salmon pink background. Top: Summer in the Park. To the left: August 22nd-24th, 2025. Free Admission. Featuring performances by Kibra, Replay Storytelling, The Grand Salto Theatre, Tribal Vision Dance, Irmão (Martin Gomes & Matheus Coelho). Little Avenue Memorial Park. 22 Little Ave., Toronto, Ontario, M9N 1K6. crossroadstheatre.org To the right: Photo of the stone gate entrance with Little Avenue Memorial Park sign in an arch between the two pillars, with three illustrated pine trees against a big yellow sun in the background, the roots of the central tree reaching into the ground below.

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.

Past event: Greyed out poster image featuring text and illustration. A cloudy light blue sky with red and white hot air balloons to the left and bottom right, with a pigeon carrying a letter at the top right. Town of York | Toronto's First Post Office Pop-up Paper Fair. First show: July 12th 2025. Second show: August 9th 2025. Whimsical & fun cards, notebooks, stickers, pins, patches, prints, keychains and many more! Free admission! 10AM - 4PM @ Toronto's First Post Office. 260 Adelaide St East

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.

Past event: Greyed out illustration on a dark background. Cream brush stroke letters that say “Little Deaths” across the centre of red and orange flames bursting from an almost burnt-out match. Below that to the right is an open, empty matchbook.

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+.

Past event: Greyed out image of a young woman wearing white, with long hair over her shoulder, looks at the camera. She is very amused. Why is that? A mature woman wearing a black top and a blue patterned scarf stands back, looking with suspicion at the younger woman. How do they know each other? Do they have a secret?

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.

Past event: Greyed out detail of an 1879 oil on canvas portrait of a woman in profile. Her eyes are closed, hair tied loosely at the back of her head, and she wears a white dress with a high frilled collar.

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.

Past event: Greyed out detail of postcard collage image featuring text and photographs. On either side, half close-ups of women's faces. In the centre, a rust brown plushy Scottish cow, with a rocky landscape, Scottish flag, castle and cloudy sky in the background, with a car driving along a highway below. Centre: A torn piece of paper with the words: Me and You and the Highland Coo. Bottom: Created by Sara Masciotra-Milstein.

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+.

Past event: Greyed out medium close-up of a man with short dark blond hair and a scruff of a beard and mustache, wearing a light plaid shirt over a light blue t-shirt. His hands grasp the sides of his head as he gazes at us, eyes wide and teeth clenched with stress.

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.