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Toronto’s wrapping up the holiday season with tons of weekend fun — from festive lights and outdoor markets to cozy concerts and skating. Here’s what you shouldn’t miss!
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Free Date Ideas in Toronto This Winter
1. The Nutcracker (National Ballet of Canada)
Celebrate the 30th anniversary of this beloved James Kudelka production, known for its intricate sets and whimsical animal costumes. This classic ballet remains a must-see holiday tradition for families across the Greater Toronto Area.
Where: Four Seasons Centre for the Performing Arts (145 Queen Street West Toronto)
When: December 27th-28th, 2025
Price: Standing room tickets are the only ones available: $12
Category: Family-friendly
2. The Polar Bear Skate
Brave participants are invited to strip down to their swimsuits for a chilly, "cheeky" lap around the outdoor skate trail. This unique Toronto tradition is a fun way to bid farewell to the year and support local clothing drives.
Where: The Bentway Skate Trail (250 Fort York Boulevard, Toronto)
When: December 28th, 2025
Price: Admission is free, but skate rental is $12.
Category: Date/Friends
3. Toronto Maple Leafs vs. Ottawa Senators
The "Battle of Ontario" heats up as these classic rivals face off on a prime Saturday night. Expect a high-energy atmosphere as fans from both cities pack the arena for one of the season's most anticipated matchups.
Where: Scotiabank Arena (50 Bay Street, Suite 500, Toronto)
When: December 27th, 2025
Price: Starts at $177
Category: Date/Friends
4. Champions of Magic: Holiday Spectacular
A team of world-class illusionists perform incredible escapes and mind-reading feats in this high-production magic show. It is an interactive experience that offers thrills and surprises for audience members of all ages
Where: Bluma Appel Theatre (27 Front Street East Toronto, ON)
When: December 27th-28th, 2025
Price: Starts at $69.99
Category: Family-friendly
5. The Distillery Winter Village
Stroll through cobblestone streets filled with artisan vendors, festive food, and the city’s most famous 50-foot Christmas tree. This is one of the final weekends to enjoy the market's cozy atmosphere before the season ends.
Where: The Distillery District (55 Mill Street, Toronto ON)
When: December 27th-28th, 2025
Price: Starts at $18.65
Category: Family-friendly
6. Cavalcade of Lights
Skate under the glow of over 300,000 LED lights and Toronto's official Christmas tree at this iconic public square. The display remains lit until 11:00 PM, providing a beautiful backdrop for evening photos and city sightseeing.
Where: Nathan Phillips Square (100 Queen St.W, Toronto, ON)
When: Until January 7th, 2026
Price: Free Admission
Category: Family-friendly
7. Christmas at the Castle
Get ready to laugh with Canada’s Comedy All Stars this Sunday! Always featuring 3 of Canada's top comedians, from Juno Award winners and TV stars, to comedy festival superstars! Use code CANADA for $5 off (limited availability).
Where: Casa Loma (1 Austin Terrace, Toronto, ON)
When: December 27th-28th, 2025
Price: Starts at $45
Category: Family-friendly
8. Sharks Exhibit at ROM
Dive into the fascinating world of sharks at the ROM, featuring everything from the Megalodon to the Hammerhead! Explore their anatomy, behaviour, and history in this thrilling exhibition on now through March 22, 2026.
Where: Royal Ontario Museum (100 Queens Park, Toronto, ON)
When: Until March 22nd, 2026
Price: Starts at $17.75
Category: Family-friendly
9. Titanic: The Artifact Exhibition
Explore reconstructed ship rooms, powerful passenger stories, and an immersive VR experience that brings the Titanic’s journey and legacy vividly to life.
Where: YZD (30 Hanover Road, North York, ON)
When: Until January 18th, 2026
Price: Starts at $39.90
Category: Family-friendly
10. Canada’s Wonderland WinterFest
The theme park turns into a winter wonderland featuring ice skating on Snow Flake Lake and millions of twinkling lights. Enjoy live holiday shows, themed treats, and select family rides in a festive, immersive environment.
Where: Canada’s Wonderland (1 Canada's Wonderland Dr, Vaughan)
When: Until January 3rd, 2026
Price: Prices may vary.
Category: Family-friendly
11. Toronto Raptors vs. Golden State Warriors
This exciting cross-conference game features the Raptors hosting the star-studded Warriors in a rare Sunday matinee. It’s a perfect opportunity to see top-tier talent like Steph Curry in action right in downtown Toronto.
Where: Scotiabank Arena (50 Bay Street, Suite 500, Toronto)
When: December 28, 2025
Price: Starts at $176
Category: Family-friendly
12. Aga Khan Museum: Light Up the Dark
The theme park turns into a winter wonderland featuring ice skating on Snow Flake Lake and millions of twinkling lights. Enjoy live holiday shows, themed treats, and select family rides in a festive, immersive environment.
Where: Aga Khan Museum (77 Wynford Drive)
When: December 27th – 29th, 2025
Price: Starts at $10
Category: Family-friendly
Community Events
1. A Date Night Paint Night
Couples paint two separate canvases that connect into one artwork, guided by an artist, with relaxed vibes, fun questions, and complimentary snacks and drinks.
Where: Artbox Studio Gallery (1226 Kingston Rd, Toronto M1N1P3)
When: December 27th, 2025 (8:00 PM – 10:00 PM)
Click here for more information.
2. Feria de Cali with Son D'Aqui, DJ Van Gogh & Dance to Live!
Enjoy a full night of salsa with dinner, a beginner-friendly dance lesson, live band performances, and a DJ keeping the dance floor moving late into the night.
Where: Lula Lounge (1585 Dundas Street West)
When: December 27th, 2025 (7:00 PM – 2:00 AM)
Click here for more information.
3. Meet Oscar the 6 Foot Dog at KidSpark
Kids can explore a pretend vet clinic, meet a giant plush dog, and learn about pet health through fun, interactive activities.
Where: Ontario Science Centre: KidSpark at Harbourfront Centre (235 Queens Quay W, Toronto)
When: December 27th – 28th, 2025 (10:00 AM – 5:00 PM)
Click here for more information.
4. Ukrainian Bandura Christmas
Experience an evening of Ukrainian Christmas carols performed by powerful voices and the magical sound of the bandura, blending traditional and modern arrangements for a festive celebration.
Where: Humber Valley United Church (76 Anglesey Blvd.)
When: December 28th, 2025 (4:00 PM – 6:00 PM)
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