It’s a packed week across Toronto and the GTA with festive markets, concerts, arena matchups and creative pop-ups. Whether you want holiday magic, a night out with friends or family fun, there’s something for everyone.

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1. Christmas at the Castle

Step into a storybook holiday as Casa Loma becomes a glittering Christmas castle. Wander through stunning décor, twinkling lights, themed rooms, and festive performances. With towering trees and magical winter scenes, this beloved annual event brings the season to life for families and holiday lovers alike.

Where: Casa Loma (1 Austin Terrace)

When: December 5th, 2025 - January 3rd, 2026 

Price: Prices start at $25 

Category: Family-friendly

Click here for the website.

2. Boursin Bistro x Emily in Paris

Step into a Paris-inspired bistro for one night only. Enjoy live jazz, cinematic décor, photo booths, fashion-illustration portraits, and signature Boursin cheese boards named after Emily’s iconic love interests. A chic, indulgent night out for fans of fine food and “Emily in Paris” vibes. 

Where: Café Renée (100 Portland St)

When: December 4th, 2025 (7 pm - 11 pm)

Price: Reservations Required. (Keep checking for availability as more spots open)

Category: Date/Friends

Click here for the website.

3. THM Holiday Retail

The Toronto History Museums Shop offers a beautifully curated selection of unique finds, from Indigenous crafts and artisan jewelry to books, games, and locally handmade treasures. Enjoy 10% off all purchases now through December 1st. Every item you take home helps support Toronto’s historic sites and the talented local creators.

Click here for the website. 

4. A Festive Night Out - Meet New Friends

Kick off the holidays with a festive night out starting at The Deck at Clarence Square for hot chocolate and a winter walk, then head to Waterworks Food Hall for games, great company, dancing, photo ops, and prize giveaways. A fun, social evening to meet new friends.

Where: Starts at The Clarence Park (7 Clarence Square)

When: December 5th, 2025 (6 pm -10 pm)

Price: $5

Category: Date/Friends

Click here for the website.

5. The Nutcracker: National Ballet of Canada

Celebrate 30 magical years of The Nutcracker as Marie and Misha embark on a dreamy holiday adventure through glittering snow, fantastical creatures, and the Sugar Plum Fairy’s palace. Set to Tchaikovsky’s iconic score, with breathtaking costumes, magical sets and timeless holiday charm. 

Where:  Four Seasons Centre for the Performing Arts (145 Queen Street West)

When: December 5th - 31st, 2025

Price: Prices start at $69

Category: Family-friendly 

Click here for the website.

6. Toronto Maple Leafs vs. Montreal Canadiens

Catch the Leafs take on the rival Canadiens in one of the season’s most electric matchups. Expect an action-packed game, roaring energy at Scotiabank Arena, and classic Toronto hockey vibes, perfect for a night out with friends, family, or fellow fans.

Where: Scotiabank Arena (40 Bay St)

When: December 6th, 2025 (Starts at 7 pm)

Price: Prices start at $279

Category: Family-friendly

Click here for the website.

7. Drawing. Drinks. Social. 

Unwind with drinks, sketching and community vibes at AGO’s Drawing. Drinks. Social. Sip, draw, and mingle in the Tanenbaum Atrium before heading into the galleries for guided drawing. Perfect for beginners or anyone looking to make art friends while enjoying a relaxed evening.

Where: Art Gallery of Ontario (317 Dundas Street West)

When: December 6th, 2025 (6 pm - 9 pm)

Price: Prices start at $55

Category: 19+

Click here for the website.

8. Mississauga Festival of Trees

Step into a winter wonderland where art, lights, local food and handmade goods meet holiday magic. The Mississauga Festival of Trees features contemporary tree-themed art installations, a vibrant artisan & culinary market, festive workshops, live music and seasonal decorations.

Where: Small Arms Inspection Building (1352 Lakeshore Road East, Mississauga)

When: December 5th - December 14th, 2025 (Times Vary)

Price: Pay-what-you-can

Category: Family-friendly

Click here for the website.

9. City of Craft Holiday Market 

Explore handmade wonders from over 60 Canadian artisans, including ceramics, knitted goods, jewelry, leather pieces, zines, prints and more at City of Craft’s beloved holiday market. Perfect for gift hunting or holiday browsing, this creative fest brings together makers and shoppers for a cozy, craft-filled celebration.

Where: The Theatre Centre (1115 Queen Street West)

When: December 5th – 7th, 2025

Price: $5

Category: Family-friendly

Click here for the website.

10. Merry Murdoch Mysteries in Concert

Join the hit CBC series for a festive holiday whodunnit. Watch a new “Murdoch Mysteries” episode on the big screen while the Toronto Symphony Orchestra performs the original score live. Expect suspense, holiday spirit, and special musical guest performances.

Where: Roy Thomson Hall (60 Simcoe St)

When: December 2nd, 2025 (Starts at 7:30 pm)

Price: Prices start at $187

Category: Family-friendly

Click here for the website.

11. One Tree Holiday

Relive the music of the beloved TV show One Tree Hill as Tyler Hilton and Kate Voegele bring their “One Tree Holiday” tour to town. Expect heartfelt acoustic-pop, nostalgic hits, and a cozy, festive concert vibe for fans old and new.

Where:  Annabel's Music Hall (200 Princes' Blvd)

When: December 5th, 2025 (Starts at 8 pm)

Price: Prices start at $35.50

Category: Date/Friends

Click here for the website.

Community Events

1. ADVOCATS BIG BAND'S ANNUAL HOLIDAY SHOW AT THE DUKE!

Enjoy a festive evening with the Advocats Big Band, playing holiday favourites and more, alongside food and drinks—all for a $15 cover supporting the band.

Where: The Duke Toronto (1225 Queen Street East, Toronto)

When: December 1st, 2025 (7:45 PM – 10:45 PM)

Click here for more information.

2. NBA: Toronto Raptors vs. Portland Trail Blazers

Cheer on the Toronto Raptors as they take on the Portland Trail Blazers in an exciting NBA matchup!

Where: Scotiabank Arena (40 Bay St., Toronto, ON M5J 3A5)

When: December 2nd, 2025 (7:30 PM – 9:00 PM)

Click here for more information.

3. Stranger Things Trivia Night - Snakes & Lattes Annex

Test your Stranger Things knowledge at a trivia night, reliving iconic moments from Seasons 1–4 and competing to be the ultimate Hawkins champions.

Where: Snakes and Lattes (600 Bloor St. West)

When: December 3rd, 2025 (7:00 PM – 9:00 PM)

Click here for more information.

4. NBA: Toronto Raptors vs. Los Angeles Lakers

Cheer on the Toronto Raptors as they face off against the Los Angeles Lakers in an exciting NBA matchup!

Where: Scotiabank Arena (40 Bay St., Toronto, ON M5J 3A5)

When: December 4th, 2025 (7:30 PM – 9:00 PM)

Click here for more information.

5. NBA: Toronto Raptors vs. Charlotte Hornets

Support the Toronto Raptors as they take on the Charlotte Hornets in an action-packed NBA game!

Where: Scotiabank Arena (40 Bay St., Toronto, ON M5J 3A5)

When: December 5th, 2025 (7:30 PM – 9:00 PM)

Click here for more information.