Explore the best of the city’s cultural scene this week, from theatre and comedy to film and music! Our Toronto Best Bets include a captivating theatre production, an exciting showcase in celebration of Black History Month, a red carpet event and an unforgettable Taylor Swift Orchestra concert.
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Morningside Red Carpet and Cast Q&A
The public is invited to attend the red carpet and Q&A of the film Morningside, directed by Ron Dias. The film explores personal struggles, relationships, and societal challenges amidst the threat of gentrification in Scarborough’s Morningside neighbourhood. The film features a talented Canadian cast including Fefe Dobson, Kiana Madeira, and Lovell Adams-Gray. More info.
When: February 20
Where: Scarborough Town Centre
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NiaFlix: A Night at the Centre
Enjoy a selection of short films from filmmakers with roots in Dominica, Jamaica, Trinidad, Haiti, and Martinique. These works explore Caribbean identity, memory, immigration, and diasporic longing, offering a unique blend of culture and art. More info.
When: February 20
Where: Nia Centre for the Arts
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Black History Month Showcase
Canadian Cyphers: Elements of Toronto Hip-Hop celebrates Canada’s vital contribution to Hip-Hop culture, with a special focus on Toronto. Featuring the legendary Dream Warriors, Haviah Mighty, Mathematik, and more, this immersive event combines live performances with an audiovisual exhibition and a collection of iconic albums, memorable flyers, and stories. Best of all, it’s free of cost! More info.
When: February 21
Where: City of Toronto Archives
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Sankofa 2025
Join Pride Toronto for the third annual Black History Month event, Sankofa: Honouring the Past, Celebrating the Present, Mapping the Future. This event celebrates the contributions of Black 2SLGBTQI+ community members, honouring those who’ve created safer spaces, championed rights, and amplified voices. Enjoy cultural food, performances by Black 2SLGBTQI+ artists in music, dance, and drag, and show off your finest Black cultural attire for a chance to win exciting prizes! More info.
When: February 21
Where: The 519
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Stitches & Scenes: Funny Face
Bring your crochet, knitting, embroidery, or any project, and stitch along to this classic film. Funny Face stars Audrey Hepburn as Jo Stockton, a bookshop keeper turned reluctant model. This colourful and charming musical, filled with dynamic musical numbers and amazing costumes by Hubert de Givenchy and Edith Head is perfect for a creative night out. More info.
When: February 22
Where: Hot Docs Cinema
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Taylor Swift Eras Encore
Experience Taylor Swift like never before with Orchestral Wonderland: Taylor Swift Eras Encore! The Toronto Concert Orchestra will bring your favourite hits like Fearless, Enchanted, and Shake It Off to life, accompanied by special guest singer Emily Power. Enjoy Taylor’s music with fun Swift-themed activities like treats, photobooths, and friendship bracelets to kick off the night. More info.
When: February 22
Where: Eglinton Grand
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Hypothetical Baby
Hypothetical Baby is a one-person show about abortion by Rachel Cairns. This heartfelt and hilarious show talks about societal factors that shape reproductive choices and the relationship between choice, change, and loss. Cairns was named “one of the country’s most original actors”, and is also the host of Aborsh, a podcast about abortion in Canada. More info.
When: February 22 – March 8
Where: Factory Theatre
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Firecracker Department Comedy Café
This month’s Comedy Café brings fresh perspectives and plenty of laughs, featuring some of the best female and non-binary comedians. It’s a great opportunity to relax, reconnect, and celebrate with the Firecracker community. Whether you’re a longtime fan or a first-timer, this event should not be missed. This month’s show will support those affected by the devastating California wildfires, with all proceeds donated to the Wildfire Recovery Fund. More info.
When: February 23
Where: The Assembly Theatre
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Toronto Postcard Club 43rd Annual Show
The Toronto Postcard Club Annual Show is Canada’s largest vintage postcard show. Discover thousands of vintage postcards for sale, organized by topic and geography, spanning from the early 1900s to modern times. Whether you’re a collector or just curious, there’s something for everyone! More info.
When: February 23
Where: Japanese Canadian Cultural Centre
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