Winter can get gloomy, especially after the holidays! January, February and even March can get a little boring, but that doesn’t mean the city isn’t buzzing with things to enjoy. We’re talking winter festivals – the ones that are so good, leaving the warmth of your home is not a problem. We’ve put together a list of a few festivals happening in Toronto this winter that we think are worth exploring.
Check it out:
DesignTO Festival returns to the city this month, bringing Canada’s largest annual celebration of design to the streets. Toronto will transform into a citywide artistic playground this January, and this year, it’s sure to spark some imagination.
Starting Jan. 23, 2026 and for 10 days thereafter, DesignTO will decorate the streets with creations that “inspire you to feel through interaction, immersion, wonder and surprise.”
When: Jan. 23 to Feb. 1, 2026
Where: Across Toronto and online
Cost: Free unless otherwise stated
Enjoy the annual festival of contemporary music by the University of Toronto. Expect 10 days of concerts, workshops and master classes as the team celebrates new music.
When: Jan. 23 to Feb. 3, 2026
Time: Varies depending on concert
Where: Various venues
Cost: Free and ticketed
The third edition of KUUMBA 365 celebrates Black culture through sound with original works from top musicians. This year, in partnership with The Power Plant, “Harbourfront Centre invites musicians Dennis Passley, Larnell Lewis and Dwight Jones respond to this season’s exhibitions by Jeneen Frei Njootli and Christina Leslie, connecting music and contemporary art,” shares organizers.
KUUMBA 365 is Toronto’s largest and longest-running Black Futures Month Festival.
When: February 2026
Time: Varies
Where: Harbourfront Centre
Cost: Varies
Celebrate the winter season with a little party — apres ski style. The Roundhouse Craft Beer Fest returns this year, featuring retro ski gear, drinks and all your friends.
Tickets are on sale!
When: Feb. 21, 2026
Time: Noon to 6 p.m.
Where: Roundhouse Park, 255 Bremner Blvd.
Cost: $48.33+
Get ready for the Toronto Sketch Comedy Festival this March!
It’s the city’s longest-running comedy festival, “created to celebrate Toronto’s storied and continued excellence in the theatrical tradition of sketch comedy.”
When: March 4 to 15, 2026
Time: Varies
Where: TBA
Cost: $129+ (one-price festival pass – access to 55+ shows on four stages by 60+ acts)
Sugar Shack TO is making a huge comeback to Toronto’s waterfront this winter!
The beloved celebration of things maple and sweet will officially return, with a new home at Harbourfront Centre this March 2026.
“We’re thrilled to bring Sugar Shack TO back to Toronto’s waterfront, and even more excited to partner with Harbourfront Centre for the first time,” said Mike Riehl, Chair of the Water’s Edge Festivals and Events Board of Directors.
“This new partnership allows us to deliver an even better experience with all the authentic maple traditions, live entertainment, and Canadian culture that families have come to love. We promised we’d be back stronger in 2026, and we’re delivering on that promise.”
When: March 14 and 15, 2026
Time: 11 a.m. to 6 p.m.
Where: Harbourfront Centre – 235 Queens Quay W.
Cost: Free
Wavelength Music Festival will bring 30+ live acts to the stage this winter across Toronto. Locations include Lula Lounge, the Art Gallery of Ontario, the Baby G, the Garrison, InterAccess, and Wavelength at St. Anne’s. Along with the music, expect a number of conversation programs and interactive activities to explore.
When: March 19 to 26, 2026
Time: Varies on show
Where: Locations vary
Cost: $26+
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