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Union Winter Roller Express

Toronto, ON

For the fourth year in a row, we're back bringing the crowd-favourite Roller Express! It's the perfect way to kick off Toronto’s festive season.Enjoy indoor roller-skating with skate rentals available on site and special themed nights like the Union Beats Skate Night, Winter Mixers, Roll and Recharge and skating lessons - all in the beautiful historic Union Station! Most events are open to guests of all ages. Please visit our website for more details.

Nov 26 - Jan 18

winter events

Spam Art Exhibition

Etobicoke, ON

Explore the ubiquitous yet humble Asian grocery store. Sam Lee visualizes Western influence in East Asian culture and food, commenting on social and political events like the US involvement in the Korean War.

Nov 5 - Jan 29

winter events

We were Promised Prosperity... Instead we got Spam Art Exhibition

Etobicoke, ON

Immerse yourself in the ubiquitous yet humble Asian grocery store. Sam Lee visualizes Western influence in East Asian culture and food, commenting on social and political events like the US involvement in the Korean War.

Nov 5 - Jan 29

winter events

Yesterday Reframed

Scarborough, ON

Discover this intimate exhibition of mixed-media drawings that investigates cultural identity, memory and the reconstruction of inherited histories. Through delicate, small and medium scale works, artist JJ Lee explores how personal and collective narratives, shaped by migration and colonization, are mediated through drawing, adding a fragile and ephemeral quality.

Jan 6-28

winter events

New Views of the Landscape Exhibition

Etobicoke, ON

Grounded in observation, uncover paintings by Jeffrey Malcolm celebrating the Canadian landscape through a contemporary lens. Each work creates new light, distance, and tone reimagining present-day approaches to colour and form and reshaping familiar terrain. About the Artist Jeffrey Malcolm is a Toronto-based artist whose work examines the Canadian landscape through a contemporary approach to colour, light, and technique.

Jan 8 - Feb 13

winter events

Sky & Bone: Realities Unbound

Toronto, ON

Come explore Sky & Bone, an exhibition featuring over thirty fine art pieces from the City of Toronto Collection alongside works from contemporary Canadian artists. Encounter personal moments that create ceremonial connections beyond everyday realities.

Nov 21 - Jan 24

winter events

Gibson House Museum - My Voice in a Quilt

North york, ON

This collective exhibition of textile artwork was handcrafted by Syrian women, all newcomers to Toronto, as part of a Toronto Arts Council Animating Historic Sites program. Each quilt is composed of individual squares handcrafted by one woman, reflecting her emotions, memories, hopes and personal stories.

Nov 2 - Feb 1

winter events

Echoes of Home: Pop-Up Exhibit at Fort York

Toronto, ON

This pop-up installation explores the compelling stories and experiences of Toronto’s diverse communities who have fought for their sense of home, belonging and identity during periods of conflict and peace. The experience installation is created in partnership with the Toronto Metropolitan University's Masters of Digital Media program.

Jan 7 - Mar 29

winter events

Pop-Up Exhibit: Making Home in Scarborough at Scarborough Museum

Scarborough, ON

Making Home in Scarborough is a vibrant pop-up installation celebrating memory, identity, and belonging through cultural traditions and objects we hold dear to our hearts in generations past, present and future. Co-created through conversation and care, community members were invited to share a meaningful object, rooted in a heartfelt story.

Oct 1 - Jan 31

winter events

Washed Up: Pop-Up Installation at Scarborough Museum

Scarborough, ON

Beginning July 1st at Scarborough Museum, experience Washed Up by Hatecopy.

Oct 1 - Jan 31

winter events

I am Scarborough - Installation at Scarborough Museum

Scarborough, ON

"I Am Scarborough" is a community-engaged installation at Scarborough Museum, created by artist Kseniya Tsoy during her Toronto Arts Council Animating Historic Sites residency. Over the course of several months, Scarborough residents and museum visitors came together to fold hundreds of origami butterflies and share their stories—their journeys, the lands their families come from, and their hopes and dreams.

Nov 1 - Feb 26

winter events

Sky & Bone presents Beading Workshops with Jenna Bjornson

Toronto, ON

Experience a hands-on beading workshop with Métis artist Jenna Bjornson, an artist grounded in storytelling and community. In this welcoming, beginner-friendly session, participants will create a 5-panel beaded flower pin backed with deer hide. All materials are provided. Jenna is Red River Métis with family ties to Fort Carlton, Saskatchewan. Jenna is a descendant of John Peter Pruden, a Chief Factor of the Hudson’s Bay Company.

Jan 8-22

winter events

winterlicious

Love local with delicious meals at more than 240 restaurants that make Toronto a true food-lover’s destination. With three-course prix fixe menus ranging from cozy favourites to vibrant global dishes, there’s something for every taste and budget.

Jan 30 - Feb 12

winter events

Cavalcade of Lights

Toronto, ON

Experience the magic of the holiday season with the much-loved Cavalcade of Lights presented by Desjardins Financial Group. With an opening night that illuminates winter’s darkness, Cavalcade of Lights is a free event that transforms City Hall and its surrounds into a dazzling wonderland. Saturdays, 4 to 10 p.m. Take advantage of free skate rentals courtesy of Desjardins Financial Group: December 6 December 13 December 20 December 27 January 3

Jan 7

winter events

The Roundhouse Winter Craft Beer Fest

Toronto, ON

Join us to celebrate Winter at the Roundhouse Craft Beer Fest! Toronto's biggest and baddest près-brew-ski party. Gather your pals, retro ski gear, long johns, and all the flannel you can get your mitts on.

Feb 21

winter events

New Vistas: Alder for the Heart

Etobicoke, ON

Uncover diverse perspectives of identity in the GTA through an exhibition that highlights the talent of early career visual artists. Curated by Humber College’s Arts Administration & Cultural Management program.

Dec 3 - Jan 14

winter events

Robert's Paintings Screening

Toronto, ON

We invite you to join us on January 15, 2026 for an exclusive exhibition walkthrough with Jesse King, curator of SKY & BONE. In collaboration with Vtape, this special screening of Robert’s Paintings (Directed by Shelley Niro) invites you to watch an intimate and deeply moving portrait of acclaimed artist Robert Houle.

Jan 15

winter events

By the Lake Book Club – 6-Event Package

Etobicoke, ON

Enjoy all six By the Lake Book Club events of 2026 for just $120. Join Humber Polytechnic alumni as they dive into conversation with leading Canadian authors. The series line-up features Maggie Helwig, Patty Krawec, Martha Bátiz, Claire Cameron, Emma Knight and Anne Michaels. Each event includes a reading, discussion, audience Q&A, book-signing and American sign language interpretation.

Feb 3

winter events

Encampment: Resistance, Grace, and an Unhoused Community by Maggie Helwig - By the Lake Book Club

Etobicoke, ON

Encampment: Resistance, Grace, and an Unhoused Community, by 2025 Toronto Book Award winner Maggie Helwig, chronicles the encampment that formed on the grounds of St. Stephen-in-the-Fields Church during Toronto’s housing crisis. Blending memoir, urban history and social critique, Helwig – an Anglican priest and activist – offers an unflinching explore systemic failures and the resilience of those forced to live outdoors.

Feb 3

winter events

Montgomery's Inn Indoor Farmers' Market

Etobicoke, ON

Join us at Montgomery's Inn for the Indoor Farmers' Market Season. Experience the best of local and farm fresh food, famous INNovator Bread, and family-friendly activities. All are invited. The indoor market runs from February 4 - May 20 and then moves outdoors.

Feb 4 - May 20

winter events

Gather for Family Day Weekend at Sky & Bone

Toronto, ON

Come exploreors are invited to participate in a self-guided collage-making activity inspired by Carl Beam’s artistic process. Using images from National Geographic, science magazines, textbooks, and newspapers which Beam often incorporated into his own work, participants can explore storytelling, memory, and community through collage. Together, these activities invites everyone to gather, create, and explore through media and contemporary art.

Feb 13-14

winter events

Gather for Family Day Weekend at Montgomery's Inn

Etobicoke, ON

Play, create, and make new traditions this Family Day at Toronto History Museums! This Family Day weekend, Montgomery's Inn invites you to gather together with family and friends. Visit the Inn for free activities, and relax in our book nook. Guests will also be invited to take a free book provided by the Children's Book fund and make a bookmark!

Feb 14-16

winter events

Gather for Family Day Weekend at Spadina Museum

Toronto, ON

This Family Day Weekend, Spadina Museum will offer a free drop-in crafting space for families and intergenerational groups to create collages using their own family photos, along with cutouts from magazines, fabric scraps and other basic art materials supplied by the museum. Staff and volunteers will be onsite to support visitors in their artmaking process, with inspiring examples and step-by-step instructions.

Feb 14 - Mar 16

winter events

Gather for Family Day at Fort York

Toronto, ON

Enjoy a full day of discovery at Fort York. Sign up young bakers to make buttery “jumbles” in a paid historic kitchen workshop, then visit the garrison schoolroom to practice slate writing and learn how soldiers’ children were taught. Catch a flintlock musket demonstration and join a discussion about how weapon technology shaped past conflicts.

Feb 16

winter events

Gather for Family Day Weekend at Colborne Lodge

Toronto, ON

Experience the magic of winter at Colborne Lodge in beautiful High Park! Snow creations, winter crafts, warm drinks and stories to warm the heart. Enjoy the chilly weather with ice building fun, outdoor games. "Seek and find" animal tracks and enjoy interpretation on the main floor of the Historic House. Please dress for the cold!

Feb 16

winter events

Gather for Family Day Weekend Storytelling at Montgomery's Inn

Etobicoke, ON

Play, create, and make new traditions this Family Day at Toronto History Museums! This Family Day weekend, Montgomery's Inn invites you to gather together with family and friends. On Monday, February 16, join us at 12 pm (noon) and 2 pm, for storyteller with Kesha Christie from Talkin Tales! Kesha will be presenting Anansi stories and African and Caribbean folktales surrounding stories about family, community, and traditions.

Feb 16

winter events

Third Voice Exhibition

Etobicoke, ON

A collaborative exhibition by three artists focused on exploring art from a materials-first perspective. Materials speak shaping a dialogue that extends beyond the artists where paint, surface and light respond becoming a unique voice in the conversation. From translucent layers to reactive surfaces, gestural marks to shifting reflections, the artists find common ground in the physicality of making.

Feb 19 - Mar 26

winter events

Gathering at the Table: A Chef in Residence Celebration

Toronto, ON

Join us at Fort York National Historic Site for a culminating dinner celebrating the culinary journey of Chef Jean Regis Raynaud as Toronto History Museums Chef in Residence. Experience a thoughtfully curated menu that honours the flavours of the African Diaspora through collaboration with fellow Chefs, Marc Kusitor, ChopTime Catering and Victor Ugwueke, of the Afrobeat Kitchen.

Feb 21

winter events

Bad Indians Book Club by Patty Krawec - By the Lake Book Club

Etobicoke, ON

Bad Indians Book Club, by Anishinaabe and Ukrainian writer Patty Krawec, is a bold exploration of Indigenous literature and the stories that challenge colonial narratives. Emerging from a year-long reading journey, Krawec blends memoir, cultural critique, and storytelling to examine works by marginalized voices and their power to reshape identity and belonging.

Mar 10

winter events

Gather for March Break: Create a Community and Historic Cookbook

Etobicoke, ON

This March Break, step into the culinary past at Montgomery’s Inn! Join us in crafting a community cookbook that blends your favorite family recipes with historic dishes from the Inn’s own collection. Explore the historic house and discover objects that tell the story of food traditions through time. Share, learn, and celebrate the flavors that connect us! Email your recipe to Montinn@toronto.ca to share your families culinary traditions.

Mar 14-22

winter events

Assimilation and Integrity

Etobicoke, ON

Journey through evocative landscapes, skyscapes, and works rooted in history and tradition that emphasize the urgency of preserving our changing environment and the need to uphold cultural integrity amid increasing digital and societal assimilation. Solo exhibition by Tatjana Hutinec. About the Artist Croatia-raised, Tatjana Hutinec is a Toronto-based visual artist displaced by the Homeland War during the 1990-s.

Apr 2 - May 7

winter events

Toronto I❤Beer Festival

Toronto, ON

Annual winter beer tasting & silent disco party with local & regional craft beer, cider & spirit vendors; two session options.

Jan 31

winter events

DesignTO Festival

Canada’s largest design festival featuring exhibitions, installations, talks and workshops across the city.

Jan 23 - Feb 1

winter events

Winterista Ice & Light Festival

East york, ON

Immersive ice and light installation with sculptural art, illuminated spaces and ice slides; family-friendly & signature adult nights.

Jan 23 - Feb 14

winter events

Toronto Tea Festival

North york, ON

Festival celebrating teas from around the world with tastings, workshops and presentations.

Jan 31 - Feb 1

winter events

New Year’s Skating Parties (City of Toronto)

Outdoor skating, free rentals, DJs, hot chocolate and winter family activities.

Jan 4

winter events

Canada’s Wonderland WinterFest

Maple, ON

Seasonal holiday event with lights, shows, skating and rides.

Jan 3

winter events

Union Winter Roller Express

Toronto, ON

Nov 26 - Jan 18

winter events

Spam Art Exhibition

Etobicoke, ON

Nov 5 - Jan 29

winter events

We were Promised Prosperity... Instead we got Spam Art Exhibition

Etobicoke, ON

Nov 5 - Jan 29

winter events

Yesterday Reframed

Scarborough, ON

Jan 6-28

winter events

New Views of the Landscape Exhibition

Etobicoke, ON

Jan 8 - Feb 13

winter events

Sky & Bone: Realities Unbound

Toronto, ON

Nov 21 - Jan 24

winter events

Gibson House Museum - My Voice in a Quilt

North york, ON

Nov 2 - Feb 1

winter events

Echoes of Home: Pop-Up Exhibit at Fort York

Toronto, ON

Jan 7 - Mar 29

winter events

Pop-Up Exhibit: Making Home in Scarborough at Scarborough Museum

Scarborough, ON

Oct 1 - Jan 31

winter events

Washed Up: Pop-Up Installation at Scarborough Museum

Scarborough, ON

Oct 1 - Jan 31

winter events

I am Scarborough - Installation at Scarborough Museum

Scarborough, ON

Nov 1 - Feb 26

winter events

Sky & Bone presents Beading Workshops with Jenna Bjornson

Toronto, ON

Jan 8-22

winter events

winterlicious

Jan 30 - Feb 12

winter events

Cavalcade of Lights

Toronto, ON

Jan 7

winter events

The Roundhouse Winter Craft Beer Fest

Toronto, ON

Feb 21

winter events

New Vistas: Alder for the Heart

Etobicoke, ON

Dec 3 - Jan 14

winter events

Robert's Paintings Screening

Toronto, ON

Jan 15

winter events

By the Lake Book Club – 6-Event Package

Etobicoke, ON

Feb 3

winter events

Encampment: Resistance, Grace, and an Unhoused Community by Maggie Helwig - By the Lake Book Club

Etobicoke, ON

Feb 3

winter events

Montgomery's Inn Indoor Farmers' Market

Etobicoke, ON

Feb 4 - May 20

winter events

Gather for Family Day Weekend at Sky & Bone

Toronto, ON

Feb 13-14

winter events

Gather for Family Day Weekend at Montgomery's Inn

Etobicoke, ON

Feb 14-16

winter events

Gather for Family Day Weekend at Spadina Museum

Toronto, ON

Feb 14 - Mar 16

winter events

Gather for Family Day at Fort York

Toronto, ON

Feb 16

winter events

Gather for Family Day Weekend at Colborne Lodge

Toronto, ON

Feb 16

winter events

Gather for Family Day Weekend Storytelling at Montgomery's Inn

Etobicoke, ON

Feb 16

winter events

Third Voice Exhibition

Etobicoke, ON

Feb 19 - Mar 26

winter events

Gathering at the Table: A Chef in Residence Celebration

Toronto, ON

Feb 21

winter events

Bad Indians Book Club by Patty Krawec - By the Lake Book Club

Etobicoke, ON

Mar 10

winter events

Gather for March Break: Create a Community and Historic Cookbook

Etobicoke, ON

Mar 14-22

winter events

Assimilation and Integrity

Etobicoke, ON

Apr 2 - May 7

winter events

Toronto I❤Beer Festival

Toronto, ON

Jan 31

winter events

DesignTO Festival

Jan 23 - Feb 1

winter events

Winterista Ice & Light Festival

East york, ON

Jan 23 - Feb 14

winter events

Toronto Tea Festival

North york, ON

Jan 31 - Feb 1

winter events

New Year’s Skating Parties (City of Toronto)

Jan 4

winter events

Canada’s Wonderland WinterFest

Maple, ON

Jan 3

winter events