Photo credit: Mila Bright Zlatanovic
Table of Contents
There’s a ton of fun events happening in Toronto this weekend that you don’t want to miss. Here are some of our favourites.
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1. The Bentway’s Winter Skating Opening Weekend
Join the celebration and take your first glide of the season under the Gardiner. Enjoy a cozy skate-and-sip experience with complimentary skate rentals, hot drinks, maple taffy, and photo moments & samples courtesy of Batiste Dry Shampoo and Hero Patches.
Where: The Bentway (250 Fort York Boulevard, Toronto, ON, Canada)
When: December 20th-23rd, 2025 (12 pm - 9 pm)
Price: Free admission
Category: Family-friendly
2. DJ Skate Nights: Opening Night
Kick off the season at DJ Skate Nights with a high-energy outdoor rink party featuring live DJs, lights and winter vibes. A fun and free Toronto tradition perfect for friends, date nights and weekend plans.
Where: Harbourfront Centre (235 Queens Quay W, Toronto, ON M5J 2G8)
When: December 20th, 2025 (Starts at 8 pm)
Price: Free admission
Category: Date/Friends
3. Kensington Market Winter Solstice Festival
The 36th annual Kensington Market Winter Solstice returns this weekend. Celebrate the Winter Solstice with lanterns, performances, a parade and more.
Where: Kensington Market (160 Baldwin Street, Toronto, ON)
When: December 21st, 2025 (6 pm - 9:30 pm)
Price: Free admission
Category: Family-friendly
Click here for more information.
4. The Alpine Merry Sheep Choir Performs In The Junction
Head over to The Junction and enjoy a one-day-only performance by The Alpine Merry Sheep Choir, spreading festive cheer through the streets on December 20th.
Where: The Junction
When: December 20th, 2025 (3 pm - 5 pm)
Price: Free admission
Category: Family-friendly
5. Don’t Get Mad Get GLAD Pop-Up
Come experience a joyful GLAD pop-up with snacks, games, samples, interactive activities, and the launch of their Don’t Get Mad, Get GLAD campaign.
Where: STACKT market (28 Bathurst St, Toronto, ON M5V 0C6)
When: Until December 28th, 2025
Price: Free admission
Category: Family-friendly
6. Hangar Skate
Lace up and hit the free 6,000-sq-ft outdoor skating rink this weekend! Keep the fun going inside the YZD Experience Centre with DJs, drop-in arts programming, and light bites available for purchase.
Where: YZD Plaza (34 Hanover Road, Toronto)
When: December 19th, 2025 - January 4th, 2026
Price: Free admission
Category: Family-friendly
7. The Winter Market at Evergreen Brick Works
Head over to Evergreen Brick Works for their winter market. Featuring 60+ vendors, food trucks, skating, workshops, live performances, and fun activities, this is something you don’t want to miss.
Where: Evergreen Brick Works (550 Bayview Ave Toronto, ON M4W 3X8)
When: December 21st, 2025 (11 am - 5 pm)
Price: Suggested donation of at least $5
Category: Family-friendly
8. Festive Lights at Ontario's Legislative Building
This Saturday, check out the festive lights at Ontario's Legislative Building. Enjoy self-guided tours of the historic Legislative Building, craft stations, sparkling lights, visits with Santa, music by Canada Handbell Service, and more.
Where: Legislative Assembly of Ontario (111 Wellesley St W, Toronto, ON M7A 1A2)
When: December 20th, 22nd, 23rd, 2025
Price: Free admission
Category: Family-friendly
9. Winter BLOOMS: Circus at the Garden
Experience a magical winter circus among the gardens with acrobatics, live performance and glowing seasonal displays. A whimsical outdoor show that blends nature, artistry and festive charm for a unique family-friendly night out.
Where: Toronto Botanical Garden (777 Lawrence Ave E, Toronto, ON M3C 1P2)
When: December 20th - 21st, 2025
Price: Prices start at $25
Category: Family-friendly
10. Winter Glow
Winter Glow is coming to an end! This is your last chance to experience the bright and festive winter carnival filled with dazzling lights, outdoor attractions, cozy treats and family-friendly activities.
Where: Sankofa Square (1 Dundas St E, Toronto, ON M5B 2R8)
When: Until December 21st, 2025
Price: Free admission
Category: Family-friendly
Community Events
1. A Glow-in-the-dark Paint Night by Artbox
A guided glow-in-the-dark paint night where you create a glowing artwork in a vibrant studio setting, with music, snacks, and a fun, beginner-friendly creative experience.
Where: Artbox (1226 Kingston Rd, Toronto M1N 1P3)
When: December 20th, 2025 (5:30 PM – 7:30 PM)
Click here for more information.
2. NBA: Toronto Raptors vs. Boston Celtics
Cheer on the Toronto Raptors as they take on the Boston Celtics in an exciting NBA matchup.
Where: Scotiabank Arena (40 Bay St., Toronto, ON M5J 3A5)
When: December 20th, 2025 (7:00 PM – 8:30 PM)
Click here for more information.
3. Puppy Love Yoga
Enjoy a relaxing yoga session made extra cute with playful puppies, plus holiday cheer and candy canes for a feel-good, festive experience.
Where: Legion (243 Coxwell Ave, Toronto, ON M4L 3B4)
When: December 20th, 2025 (12:00 PM – 4:00 PM)
Click here for more information.
4. National Ballet of Canada: The Nutcracker
Celebrate 30 years of The Nutcracker, a magical holiday ballet filled with enchanting characters, stunning sets, and Tchaikovsky’s timeless music.
Where: Four Seasons Centre (145 Queen St W, Toronto, ON M5H 4G1)
When: Until December 31st, 2025
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