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Think winter means staying in? Think again. January is packed with exciting events across the city, and here are some of the best things to do in Toronto this month!
Related Posts:
Best Indoor Date Ideas in Toronto
The Best Winter Weekend Getaways Near Toronto
1. Halsey: Back To Badlands Tour
Halsey is coming back to Toronto for three back-to-back shows at History Toronto. Fans can expect high-energy performances and an unforgettable live experience.
Where: History Toronto (1663 Queen St E)
When: January 9th, 10th and 11th, 2026 (7:00 PM)
Price: Starting at $193
Category: Date/Friends
2. Vision Board Making Social
Kick off 2026 with intention at this Vision Board Making workshop featuring guided goal setting, creative time, and a chance to meet new people. Enjoy bubbly, cupcakes, a live raffle, and take home a free goodie bag valued over $40.
Where: Centre for Social Innovation (192 Spadina Ave)
When: January 11th, 2026 (2:00 PM)
Price: Starting at $37.61
Category: Date/Friends
3. Roller Express
Union Winter Roller Express transforms Union Station’s TD West Carriageway into a lively indoor roller-skating experience with free skate rentals and lessons for all skill levels. There are even themed DJ skate nights to keep the winter vibes going.
Where: Located on the northwest side of Union Station, one level below the Great Hall, with direct street access from York Street.
When: Daily until January 18th, 2026 (times vary)
Price: Free, just reserve your spot
Category: Family-friendly
4. Toronto International Boat Show
Canada’s largest indoor boat and water-life event, featuring the latest in boating, fishing, paddling gear, and marine tech. With hands-on exhibits and expert advice, it’s the perfect place to get inspired for your next water adventure.
Where: Enercare Centre (100 Princes' Blvd)
When: January 17th - January 25th, 2026 (times vary)
Price: Starting at $26
Category: Family-friendly
5. Jamaica in January 2026
Escape the January chill and enjoy a burst of island heat right here in Toronto. Warm up, relax, and soak in the vibrant tropical vibes without leaving the city.
Where: STACKT Market (28 Bathurst St)
When: January 17th, 2026 (11:00 AM)
Price: Free admission
Category: Family-friendly
6. Singles Mixer - New Year, New Connections!
Meet new people and spark fresh connections at this fun singles mixer. Set inside one of Toronto’s favourite arcade bars, it’s a relaxed night of games, music, and mingling for singles aged 28 to 55.
Where: GRETA Bar Toronto (590 King Street W)
When: January 21st, 2026 (7:00 PM)
Price: Starting at $17.55
Category: Date/Friends
7. DesignTO
The 2026 DesignTO Festival offers 100+ art and design experiences across the city, including in-person exhibitions, sculptural works, textile art, immersive installations, window displays, and interactive showcases. A small number of listings also offer online or hybrid participation options.
Where: Various locations
When: January 23rd - February 1st, 2026 (times vary)
Price: Most events are free, with select programs ticketed or requiring RSVP
Category: Family-friendly
8. Winterista
Winterista transforms Toronto’s Motorista Studio into a month-long winter wonderland of towering ice sculptures, a giant slide, immersive light art, live carving demos, and cozy lounge vibes. It’s a celebration of winter fun for all ages.
Where: 25 Commercial Rd, Unit 9, East York
When: January 23rd - February 14th, 2026 (10:00 AM)
Price: Free, just reserve your spot
Category: Family-friendly
9. Toronto Maple Leafs
We have you ready for every puck drop!
Jan 10th - INDIGENOUS CELEBRATION | Toronto Maple Leafs v Canucks
Jan 19th - Toronto Maple Leafs v Minnesota Wild
Jan 21st - Toronto Maple Leafs v Detroit Red Wings
Jan 23rd - Toronto Maple Leafs v Vegas Golden Knights
Jan 25th - NEXT GEN GAME | Toronto Maple Leafs v Colorado Avalanche
Jan 27th - SITTLER 10PT 50TH ANNIVERSARY | Toronto Maple Leafs v Buffalo Sabres
Where: Scotiabank Arena (40 Bay St)
Price: Starting at $90.75
Category: Family-friendly
10. Toronto Raptors
Don’t miss a match-up!
Jan 11th - Toronto Raptors vs. Philadelphia 76ers
Jan 12th - Toronto Raptors vs. Philadelphia 76ers
Jan 16th - Toronto Raptors vs. LA Clippers
Jan 28th - Toronto Raptors vs. New York Knicks
Where: Scotiabank Arena (40 Bay St)
Price: Starting at $58.75
Category: Family-friendly
11. WWE Monday Night RAW
Get ready for an epic showdown as wrestling superstars take over Scotiabank Arena. Fans can expect high-energy action, unforgettable moves, and a night full of thrills.
Where: Scotiabank Arena (40 Bay St)
When: January 26th, 2026 (7:30 PM)
Price: Starting at $115.50
Category: Family-friendly Click here for the website.
12. Winterlicious
Winterlicious is Toronto’s winter food festival, where over 240 local restaurants serve up special three-course prix-fixe menus for lunch and dinner. It’s a delicious way to discover new spots and support the city’s vibrant dining scene.
Where: Various locations
When: January 30th - February 12th, 2026 (times vary)
Price: Starting at $20
Category: Family-friendly
13. Puppy Yoga & Sweet Treats
This feel-good class pairs a relaxing, instructor-led yoga flow with time to connect and cuddle with adorable puppies in a small-group setting. With mats provided, a thoughtfully balanced pup-to-participant ratio, and wholesome treats like organic protein bars from The Nutrition Bar, it’s the perfect way to unwind, smile, and recharge.
Where: 659 Yonge Street, Toronto
When: Various dates/times
Price: Originally $60 (take advantage of their $50 sale while it lasts)
Category: Date/Friends
14. Toronto Public Library
Register for free classes run by Toronto Public Library. You and your child can learn 3D Design, Photoshop, and Web Design. Programs also include classes for kids under 10 and teens that build technology skills and creativity – including Maker Clubs, Lego Challenges, Maker Drop Ins, and K’Nex Club.
Where: Various library locations
When: Refer to their ongoing schedule
Category: Family-friendly
15. Unwind with a Spa
Whether you’re keeping it local or heading just outside Toronto, these spas make it easy to plan your next self-care day.
📍510a Front St W, Unit 100, Toronto
📍 3210 Line 3 N, Oro-Medonte, ON L0L 2L0
📍 324183 Mt Elgin Rd, Mount Elgin, ON
📍 3275 Hwy 7 Unit 2, Markham, ON
📍 102 Yorkville Ave, Unit 5 Toronto | 556 King St W, Toronto
📍 602 King St W, Toronto
📍 181 Wellington St W, Toronto
📍 4015 Cochrane St, Whitby, ON
📍 152 Grey County Rd 21, The Blue Mountains, ON L9Y 0K8
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