Artists and art enthusiasts will be thrilled to know that there is a stacked lineup of Toronto events to explore this week. From DesignTO Festival showcasing works that promote meaningful change to Glow in the Dark Paint Night welcoming beginners and seasoned painters for a colourful gathering, there is lots to see and do in the coming days for those wanting to put their creativity to the test. Our Toronto Best Bets features exciting exhibitions and winter festivals that you won’t want to miss.
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Urban Myths
Celebrating Sybil Goldstein’s undeniable legacy, Urban Myths presents a rare opportunity to experience the full spectrum of her artwork, including many pieces that have never been publicly exhibited before. Since her passing in 2012, Goldstein’s work has been kept in a storage space by her family in Toronto, up until now. Through this exhibition, people will get to see her long-hidden pieces, many of them capturing urban culture. With energetic lines and rough brushwork, Goldstein’s artistic vision captures the fleeting movements and moments that surrounded her, reaffirming her place within the cultural history of Toronto. More info.
When: Starting January 20
Where: Koffler301
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Dead of Winter
Halloween might be months away, but Dead of Winter promises to give you goosebumps with 6 original horror plays made by local talent. Brace yourselves for a terrifying venture, featuring different guest musicians performing in the dark. Endless scares await at this mysterious event, which supports indie artists in the creation of new innovative works and brings the community together over their shared appreciation for the horror genre. More info.
When: January 21-25
Where: Red Sandcastle Theatre
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Generation Women Canada
In this exciting gathering, women from all ages will get to share their stories about letting go. From leaving jobs that no longer served them to closing the door on toxic relationships, the experiences you’ll hear about will likely make you feel seen and empowered to also strike the match and move away from the wreckage. Listen to tales of liberation and fallout from performers in their twenties all the way to their seventies, each eager to share lessons learned and offer valuable advice. More info.
When: January 22
Where: The Lounge at Live Nation Canada
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Glo’d Up: Glow in the Dark Paint Night
Kick off the new year with a vibrant paint night at the Nia Centre, where participants will be introduced to luminous paint techniques and have fun in a community-building environment. No painting expertise required to join this colourful and creative meet-up, with all materials available on site. Just relax and connect, while making your own glowing masterpiece. Participants are automatically granted a complimentary drink upon arrival, which will definitely set the tone for the painting and mingling. More info.
When: January 22
Where: Nia Centre For the Arts
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First Drafts
A mini Degrassi reunion is in store at Second City’s latest showcase, First Drafts. Watch as well-known names like Lauren Collins and Andrea Lewis do a live table reading of some of the funniest new scripts from across Canada. Tag along for an evening where Toronto’s top performers bring humour and levity to the stage, bringing to life hidden gems that could likely become Canada’s next great TV comedy. With guest stars, sneak peeks, and lots of other surprises, this is a FREE opportunity to support local artists. More info.
When: January 22
Where: The Second City
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The Interior Design Show
Wanting to give your home a makeover and are unsure where to start? The Interior Design Show is the ideal place to get insights on decor and furniture shopping. With several booths featuring global and Canadian designers ready to give you some tips on home renovation, this event is a must for anyone looking to make their living space more comfortable and chic. Get inspired by the beautiful displays, watch seminars, network with industry experts, and be a part of Canada’s largest design party of the year. More info.
When: January 22-25
Where: Metro Toronto Convention Centre
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2026 DesignTO Festival
This festival is all about making meaningful change through art. DesignTO is a 10-day event that brings people together with the goal of designing a better future that is more sustainable, just, and joyful. With 100 + free exhibits and activities happening in person and online, people can join in no matter where they are. Check out sculptural landscapes, window installations, and art exhibitions, as well as participate in trivia nights, embroidery workshops, and panel discussions about art-making in the digital era. More info.
When: January 23-February 1
Where: Multiple venues
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Winterista
For the first time ever, a multi-day winter festival will take place, adding a layer of warmth to this chilly season. Step into a winter wonderland at Winterista, an event that features massive ice sculptures, live carving, a giant ice slide, an illuminated ice bar, and upbeat parties. Bound to be Toronto’s new tradition, Winterista’s goal is to bring families and creatives together in an immersive experience, with photo ops and hands-on winter fun. For those wanting to attend the festival’s signature fashion night, make sure to secure a staple coat and fur accessories to match the Après-ski theme. More info.
When: January 23-February 14
Where: 25-45 Commercial Road
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Sankofa’s Pen Literature Celebration
This premier event showcases the Black literary voices shaping Canada’s book sector. Sankofa’s Pen Literature Celebration will include a dynamic open mic book tasting, expert panel discussions, and an awards show that’ll recognize authors and illustrators. Commemorating the twelfth anniversary of Sankofa’s Pen, attendees will experience a rare opportunity to engage with book creators, find their next reading venture, share insights on representation, and learn about the personal journeys behind writers and illustrators’ stories. More info.
When: January 24
Where: Worth Gallery
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#BeyondTO Series 2026 – Wayqeycuna
Tiziano Cruz’s Wayqeycuna is part of the #BeyondTO Series, and it presents an intimate look at the artist’s childhood and his search for community. Based on archival work, this piece explores racial hierarchies and structures of domination that devastate cultural, vital and collective traces. Wayqeycuna inspects Cruz’s childhood memories of the interior Northern Argentina with political manifestos on the art market and class privilege. More info.
When: January 24-25
Where: Theatre Passe Muraille
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