Toronto’s official holiday season kicks off this weekend with tree-lighting ceremonies across the city. That being said, there are a lot of things to do in Toronto this weekend, totally holiday-related and will put you in the festive mood.

From ongoing events to weekend-only adventures, holiday-filled, and more! Toronto is jam-packed with the best things to do, so saying you’re bored is out of the question.

We’ve got so many things to do in Toronto this weekend, and so little time.

Check out what’s in store for you this weekend.

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Holiday Magic 2023

Kick off the holidays with the exciting return of Holiday Magic on November 25th. The Bloor-Yorkville BIA welcomes all to enjoy the Christmas spirit with its tree lighting ceremony taking place on Cumberland Street and at the Village of Yorkville Park.

This year’s event will be hosted by award-winning Singer and TV Host, Keshia Chante and includes a live performance from five-time JUNO Award-winning Canadian Jazz singer and songwriter Matt Dusk.

Expect to sing along to holiday classics like “Let it Snow,” “Jingle Bells,” and “White Christmas.” Juno-Nominated, Toronto-based singer-songwriter and producer, Barbra Lica will be opening for Dusk and will perform their new single “Rocking Rudolf”.

When: November 25th from 5 PM to 7 PM
Where: Yorkville BIA

Willowdale Christmas Market

The third annual We Love Willowdale Christmas Market & Walking Parade kicks off on November 25th from 2 PM to 9 PM.

North York’s Mel Lastman Square will transform into an outdoor market with 60 local vendors, food trucks, and live entertainment.

Sip on hot chocolate, treat yourself to some Tiny Tom donuts, and support local businesses while exploring the market.

When: November 25th from 2 PM to 9 PM (Parade at 5 PM and tree lighting at 6:30 PM)
Where: Mel Lastman Square – 5100 Yonge St
Cost: FREE (donations accepted)

Sponsored Pick: CF Winterville at CF Toronto Eaton Centre

The tree is coming back to Toronto Eaton Centre and this year’s experience is shaping up to be bigger than ever. Hosted by Canadian rock legends Barenaked Ladies, enjoy the magical countdown, an EPIC snow show and Toronto Children’s Chorus, and the classic tree lighting at exactly 6 PM on Wednesday, November 15th. And that’s not all! Stop by selected CF shopping centre locations across the GTA between Friday, November 17 and Sunday, December 24, to get your pictures taken with Santa! His schedule looks pretty full already, so make sure to book in advance!

Pictures with Santa

When: Friday, November 17 until Sunday, December 24

  • CF Toronto Eaton Centre, 220 Yonge St, Toronto
  • CF Fairview Mall, 1800 Sheppard Ave E, Toronto
  • CF Shops at Don Mills, 1090 Don Mills Rd., Toronto
  • CF Markville, 5000 Hwy 7, Markham

Cost: $15 for groups up to 6

Cavalcade of Lights – Tree lighting ceremony

Every year, the Cavalcade of Lights takes over Nathan Phillips Square with a dazzling array of holiday lights and offerings. According to the city, the square will be set aglow with 300,000 energy-efficient twinkling lights, interactive displays, and festive décor around the beloved public skating rink.

On November 25, everyone is welcome to join the opening night celebration and enjoy the musical performances, ice skating, and more. Expect an evening of festive activities, including a list of entertainment from multiple cultural backgrounds.

The evening will also include the lighting of the city’s official Christmas tree. This year’s tree is a 55-foot, majestic white spruce tree that was grown in Baldwin, Ontario.

When: November 25th, 2023 from 3 PM to 11 PM
Where: Nathan Phillips Square

Sponsored Pick: Juno Veterinary Clinic

Say goodbye to overbooked appointments, stressed-out pets, and pricy bills you can’t comprehend. Juno’s Toronto vet clinic is changing the way you care for your pets, with 24/7 virtual care via their mobile app, upfront pricing, modern, stress-free clinics (including cat-only rooms), and other benefits for even the pickiest pet parent. Check them one of their two Toronto locations, with a third on the way this fall.

When: Anytime
Where: 11 Industrial Street (Leaside), 1073 Yonge Street (Summerhill), or 2440 Bloor Street West

Toronto Santa Claus Parade

You better watch out, you better not cry, you better not pout, I’m telling you why. Santa Claus is coming to town! And it’s this weekend at the original Toronto Santa Claus Parade. The beloved event is returning to give our city a huge dose of holiday cheer this November.

This parade has been a Toronto tradition since 1905 and this year, it will delight the city once again.

All are welcome to gather and witness the amazing floats make their way through the streets — with Mrs. Claus and Santa in town, of course!

When: Sunday, November 26th at 12:30 PM
Where: Christie Pits Park to St. Lawrence Market – see route map here

Sponsored Pick: Holiday Bothy at the Park

Get ready for a rustic, winter cottage escape right in the heart of Toronto’s Yorkville. The Holiday Bothy at the Park is a trendy new festive pop-up restaurant that combines curated food and drinks with a cozy, cottage atmosphere. The pop-up will be in town from November 24th until January 1st, weekly Thursdays through Sundays. Each night will feature live DJ entertainment, delicious eats, and cozy, festive decor. Stop by, gather, and stay awhile.

When: November 24 until January 1st, 2024, Thursdays through Sundays

  • Thursday & Friday: 4 PM – 12 AM
  • Saturday: 12 PM – 12 AM
  • Sunday: 12 PM – 10 PM

Where: Park Hyatt Toronto, 4 Avenue Red, Toronto

Outdoor ice skating

It’s time to sharpen up those skates and get your warmest gear out. Toronto’s outdoor skating season kicks off this weekend as outdoor artificial ice rinks will officially open for all to enjoy, this Saturday.

From local parks to the city’s popular outdoor skating rinks, Toronto offers great skating options – east to west. According to the city, Toronto’s outdoor rinks typically open in late November and last up until March. So that means you have plenty of time to hit the ice and practice those skills.

When: Opening November 25th
Where: Outdoor skating rinks across the city

Sponsored Pick: Game night on a weeknight? Try these tea-infused mocktails instead

You can’t help it if the big game is on a Tuesday. But you CAN still enjoy it without waking up on Wednesday in a world of hurt. These 10 tea-infused mocktail recipes with Traditional Medicinals are tasty, wintery, and perfect for sharing with all your game-day buddies. It’s all the delicious satisfaction without any of the consequences. Now, if only your team could win…

Canada’s Wonderland WinterFest

The annual WinterFest kicks off on November 17th and is sure to be full of fun and festive activities, including ice skating on Snow Flake Lake, live shows, millions of spectacular lights, and hundreds of sparkling trees throughout the park.

This one-of-a-kind event transports you to a new world, full of stunning luminous displays, ambient holiday lights and festive tunes.

When: Until January 6th, 2024 (Select nights)
Where: Canada’s Wonderland
Cost: From $29.99 per person

Sponsored Pick: MOCA Museum

Experience incredible contemporary art at MOCA Toronto!  From towering installations to a stream of found and hand-crafted objects to a fresh take on portraiture, immerse yourself in spectacular art at MOCA. If you visit often during the year, you might want to consider getting an annual membership. 🤔 It’s only $25 per year and comes with free admission, exclusive Members-only events, discounts with neighbourhood partners, and more. 

Cost: Membership fee $25
Where: MOCA Toronto, 158 Sterling Rd

Window Wonderland

Toronto’s Junction neighbourhood is transforming into a free outdoor art gallery with 20 augmented reality window installations and five murals. Window Wonderland returns this November and here’s what to know.

The fourth annual event kicks off on November 24th and runs until January 31st, 2024. This urban art walk features artwork designed by local and international artists.

Visitors can bring the artwork to life using an AR app, Artivive – a first of its kind for the city.

When: November 24, 2023 to January 31, 2024
Where: Along Dundas St W – map

One Of A Kind Show

The One Of A Kind show is coming back to Toronto and there’s no better place to cross gifts off your list!

From November 24th to December 4th, the OOAK show will take over the Enercare Centre and more than 600 artisans from all over Canada will showcase their extensive selection of goods.

You can expect to find a wide range of craft goods including houseware items, clothing, art pieces, sweet treats, and jewelry.

When: Until December 3rd, 2023
Where: 100 Princes’ Blvd – Enercare Centre, Exhibition Place
Cost: $18 per adult