December is only days away, meaning that the city is already gearing up for Christmas. With ice skating rinks opening up and winter art exhibits returning for the holidays, this is an exciting time to explore Toronto’s landmarks and beloved neighbourhoods. From Union Winter to Cavalcade of Lights, here are our Best Bets for what to see and do in the city this week. 

 

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Holiday Markets

The jolly season is here, meaning that there are several holiday markets throughout the city. From the Distillery District filled with festive pop-up shops to the STACKT Market getting a holiday makeover, there’s plenty of places to go for your Christmas shopping. In our curated guide, we share over 20 market options to check out, supporting local businesses in the process. More info.

 

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Union Winter 

Let the good times roll by heading to Union Station’s indoor roller rink. With free roller skate rentals and skating lessons for beginners, this is the ideal winter activity for friends and family. In order to secure your time slot on the rink, make sure to pre-register on the site and arrive 15 minutes early. TD credit card holders can skip the entrance line through the priority entrance on a first come, first serve basis. More info.

When: Starting November 26

Where: Union Station

 

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Robin Hood: A Very Merry Family Musical

Join Robin and her friends on a medieval romp through Torontoshire, in this hilarious and interactive musical. From venturing through High Park to facing off the greedy Prince John, Robin Hood: A Very Merry Family Musical invites audiences to an entertaining panto experience. Kids are welcome to laugh out loud, sing along, boo the villain, and help out the heroes. More info.

When: Starting November 27

Where: Elgin and Winter Garden Theatre

 

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One on One: Where We Bloom Photo Exhibition

This upcoming photo exhibition spotlights the sisterhood cultivated during last summer’s One-on-One mentorship. Every year, Kickback welcomes a cohort of young girls to explore the outdoors, discovering more about themselves in the process. In partnership with Arc’Teryx Toronto, the exhibition will focus on some of the women who took a chance and joined the cohort on summer adventures year after year. With soundspaces by BadBadNotGood and featured photography by Yasmine Omar & Isabel Okoro, this night will be all about reminiscing on special memories. More info.

When: November 27

Where: It’s OK* Studios

Cavalcade of Lights

This free, wintry event will light up City Hall and its surroundings. Cavalcade of Lights will feature a glittering tree, a public skating rink (you can bring your own skates or rent them on site), and gorgeous light installations that will surely put you in the Christmas spirit. The opening night celebration will take place this Saturday, with the tree-lighting ceremony beginning at 6:30 pm. More info.

When: Starting on November 27

Where: Nathan Phillips Square

 

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One of a Kind Christmas Show

The One of a Kind Christmas Show returns this week, providing visitors with the ultimate shopping opportunity. From purchasing Canadian-made artwork to home decor essentials, this event has everything you need to prepare for the holiday season. 30% of this year’s vendors are new makers, so you will be supporting local businesses that are just starting out with every gift purchase. Make sure to check out the brand-new Vintage Section, stroll through the European-style Christmas market, and delight in tasty treats at the Flavours Section. More info.

When: November 27-December 7

Where: Enercare Centre, Exhibition Place

Thrive Art Exhibit

Thrive Art Exhibit is a three-day arts and storytelling festival that gives a platform for Indo-Caribbean voices to share their creativity. From displaying visual art pieces to putting on live performances, this is a must-attend event for artists, writers, and performers to get together and foster connection. Every day has something special to offer, including short film screenings, dance showcases, and a crafts market. More info.

When: November 28-30

Where: 1357 Dundas St. W

 

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Mr. Dressup to Degrassi

Toronto was a global player for kids TV in between 1952 and 1994. Taking this into consideration, the Museum of Toronto invites people to reminisce on that period through a nostalgic exhibition. Paying homage to four decades of children’s programming, Mr. Dressup to Degrassi will feature classic clips, reimagined sets, and beloved puppets that will surely take you back to your own childhood. Not only is this a tribute to kids TV, but it’s also a love letter to the city that taught people to laugh and grow up through the screen. More info.

When: Starting on November 28

Where: Harborfront Centre

 

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Window Wonderland

Toronto’s award-winning winter art exhibit will take over the Junction for the sixth year in a row, making the region a literal Window Wonderland. This open-air gallery presents 20 artist-designed storefront windows,11 vibrant murals, and several installations brought to life with augmented reality. Window Wonderland is presented in collaboration with the Artvive app, which transforms static artwork from around the globe into immersive digital experiences. On December 20, catch a one-day-only performance by The Alpine Merry Sheep Choir, as they perform staple holiday tunes. More info.

When: Starting on November 28

Where: The Junction BIA

Winterfest 2025

The Harbourfront Centre will become a go-to spot for the holidays. Starting this week, people can grab festive bites at the Winter Feast Lane, hop on the Harbourfront Express, and get lost in the Winter Maze. There will be a Christmas tree lighting ceremony on Friday, as well as live music from Steven Taetz and a comedy showcase by Trixx and Friends. During the weekend, attendees will also get to enjoy an unforgettable performance from the NorthFIRE Circus and sing along to Christmas carols with The Baker Street Victorian Carollers. More info.

When: Starting on November 28

Where: Harbourfront Centre

 

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Queer Zine & Local Author’s Book Fair

Treat yourself or a loved one to a local book or queer zine from this fair, brought on by one of the world’s oldest 2SLGBTQIA+ bookstores. Taking place in Glad Day’s newest location, this indoor market will welcome over 30 vendors, as well as host live performances from Musa May Cry & Geordie Gordon. Those who stick around until 7 pm will also get to celebrate the book launch of Up:Rising — A Collection of Rebellious Imaginings from Authors with Lived Experience of Mental Health & Addictions. Although the event may be free, if you register in advance, you will automatically be granted a free zine and book copy upon arrival. More info.

When: November 30

Where: 32 Lisgar Street