Despite the cold weather locking many inside, Toronto has not fallen short of creative festivals for those willing to embrace the conditions. From leading programs such as DesignTO and the Interior Design Show to Window Wonderland, this week Best Bets may help you celebrate  the ever-changing seasons!

Photo by Atsushi Nishijima


Ava DuVernay directs a story on the nuance of discrimination, inspired by Isabel Wilkerson’s life and bestselling book, Caste: The Origins of Our Discontents. The film’s North American premiere will take place in Toronto with a pre-recorded introduction from DuVernay to the screening. The film follows Isabel Wilkerson, the first African-American woman to win a Pulitzer Prize for her journalism work. Origin stands as an encompassing film on how a journalist’s journey can impact the new world. More info.

When: Opens January 18

Where: TIFF Lightbox Theatre

(Nearly) Nude Tuesdays at Artists 25

Like all artistic endeavours, new mediums, styles, and figures will always be difficult to tackle at first glance. Luckily, Artists 25 is hosting an uninstructed nude figure drawing class to practice your studio skills! This bi-weekly, drop-in session will allow attendees to gain a better understanding of anatomy in the arts. Those who attend are invited to bring their own drawing supplies and draw from a live model.This is definitely an artistic experience you would not want to miss! More info.

When: January 16 & 30

Where: A25 Nonprofit Studio

Interior Design Show

Looking beyond the conventions of furniture, the Interior Design Show celebrates and promotes the best in both global and Canadian design. Since its launch in 1999, this show has become one of the most successful recurring design events in Canadian history. This immersive, interactive, and inspiring event seeks to inspire design ideas and invite viewers to think about the spaces they curate. More info.

When: January 18 – 21

Where: Metro Toronto Convention Centre North Building

Photo by 2024 DesignTO Festival


Best known as Canada’s leading and largest annual design festival, DesignTO returns for another year of programming across the city. Multidisciplinary artists around the city will be transforming Toronto into their creative playground with over 100 free exhibitions and events through January. Through their vision to make art accessible for all participants, DesignTO will include presentations and educational programming to increase public knowledge of design. More info.

When: January 19 – 28

Where: Various locations across Toronto

Photo by Feeling 22

Taylor Swift Tribute Show

Though Taylor Swift’s Toronto shows are not for another 10 months, it is never too early to refresh on her greatest hits! A live Tribute to Taylor Swift will span the superstar’s entire career for a third straight year. “Feeling 22” will feature over 35 songs performed by Canada’s top indie country/pop artists. Set for all ages, this show gives all Swift fans a chance to experience live music with friends and family. More info.

When: January 20

Where: The Rec Room 

Photo by Women's Art Association of Canada

Black and White Exhibit 

To further explore the emotive and diverse possibilities of light and shadow pieces, the Women’s Art Association of Canada announces their 2nd annual Black and White Member’s 2024 Exhibition. When the notions of art are limited to colourful, vibrant pieces, discover how two-tone pieces can enhance expression. The reception will be hosted inside the historic home of the Women’s Art Association of Canada with artists in attendance! More info.

When: January 20 

Where:  Dignam Gallery & Ruth Upjohn Gallery 


Wintersong Music Festival 

Headlined by Wintersleep, the 5th annual Wintersong Music Festival in Stouffville, Ontario will feature over 100 acts across 15 venues! This celebration of community, music, and culture brings warmth amidst the chilly weather. For those on the search to expand their musical palette, this festival has you covered with headlining artists such as Vice Locker and Maylee Todd! More info.

When: January 19 – 20

Where: Stouffville 

Photo by S. Medeiros

The Junction 4th Annual Window Wonderland 

As the Winter season approaches an end, this is your last chance to catch Toronto’s award-winning winter art exhibit, Window Wonderland. This magical urban art walk transformed the Junction into a free outdoor gallery! Featuring AR window installations on local businesses, sidewalk art, and murals, local and international artists all contributed to the vibrancy of this neighbourhood. Take your phone and go for a stroll to watch these creations come to life! More info.

When: November 24 – January 31

Where: The Junction