Toronto’s packed this week! From food festivals and pop-ups to live sports, comedy, art, and winter fun, there’s something for every vibe.

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1. Winterlicious

Winterlicious is back for the 2026 season! Explore cuisines from around the world at over 240 Toronto restaurants, with three-course prix fixe lunch and dinner menus available at various price points that best suit your budget. Featuring cozy favourites to vibrant global dishes, you’re in for a delicious treat.

Where: Various locations‍

When: January 30th - February 12th, 2026‍

Price: Prices start from $20‍

Category: Date-friends

Click here for the website.

2. KFC Canada and Matty Matheson Pop Up‍‍

Enjoy a bold, indulgent menu of fried chicken sliders, poutine, and sandwiches crafted by Matty Matheson, with weekly secret items and a pop-up experience for fans to taste and celebrate.

Where: 1221 Dundas Street West

When: January 26th, 2026 (2 pm - 5 pm)

Price: Prices varies per item‍

Category: Date-Friends

Click here for the website.

3. Steve Schapiro: Being Everywhere

Explore the life and work of photographer Steve Schapiro through his iconic images, capturing six decades of cultural and social moments with unmatched skill and insight.

Where: Cineplex Yonge-Dundas and VIP (10 Dundas St E #402)

When: January 26th, 2026 (Starts at 7 pm)

Price: $15.50‍

Category: Date-Friends

Click here for the website.

4. SITTLER 50TH ANNIVERSARY - Maple Leafs

Celebrate a hockey legend’s milestone while watching an exciting game between two top teams, full of fast-paced action and memorable moments on the ice.

Where: Scotiabank Arena (40 Bay St)

When: January 27th, 2026 (Starts at 7 pm)

Price: Starts at $118‍

Category: Date-Friends

Click here for the website.

5. Toronto Raptors Game

Watch an exciting basketball game as two top teams face off, with fast-paced action, high-energy plays, and plenty of scoring moments.

Where: Scotiabank Arena (40 Bay St)

When: January 28th, 2026 (Starts at 7:30 pm)

Price: $89.65‍

Category: Family-friendly

Click here for the website.

6. Kathy Griffin: New Face, New Tour

Laugh along with Kathy Griffin as she delivers her sharp, hilarious, and unapologetic comedy in a brand-new tour filled with stories and laughs.

Where: Elgin & Winter Garden Theatres (189 Yonge St)

When: January 29th, 2026 (Starts at 7 pm)

Price: $68.94‍

Category: Family-friendly

Click here for the website.

7. Art Hive at MOCA

Join a free, drop-in art session to create skyscapes inspired by mood and emotion, experiment with materials, and connect with others in a supportive, mindful space.

Where: MOCA Toronto (158 Sterling Rd., Toronto)

When: January 29th, 2026 (5 pm-8 pm)

Price: Free‍

Category: Date-Friends

Click here for the website.

8. Trivia Night Toronto

Test your knowledge in a fun trivia night while raising funds to support cancer research and provide vital support for Canadians affected by cancer.

Where: Revival Event Venue (783 College St, Toronto)

When: January 29th, 2026 (Starts at 7 pm)

Price: RSVP‍

Category: Date-Friends

Click here for the website.

9. APIK Mississauga

Watch skiers and snowboarders tackle a high-speed, rainbow-filled course, compete for cash prizes, and enjoy demos, food, music, and games at this free winter sports festival.

Where: Celebration Square, Mississauga‍

When: January 30th-February 1st, 2026 (Starts at 7:15 pm)

Price: RSVP‍

Category: Date-Friends

Click here for the website.

10. Toronto Home + Backyard Show 2026

Explore ideas and products for home and backyard improvements, from landscaping and pools to patios and furniture, to get a head start on your dream outdoor space.

Where: The International Centre (Hall 2 6900 Airport Rd Mississauga)‍

When: January 30th - February 1st, 2026 (Times vary)

Price:  Adult $15, Senior $13, Kids (ages 13-17) $13.00

Category: Family-friendly

Click here for the website.

11. Twilight Symphony at the Castle

Enjoy intimate, candlelit concerts with live orchestral music, featuring rock, Broadway, and opera performances in a magical historic setting.

Where: Casa Loma (1 Austin Terrace, Toronto)‍

When: January 30th-March 7th, 2026 (Starts at 7 pm)

Price:  $70 + tax per person‍

Category: Family-friendly

Click here for the website.

12. Toronto Tea Festival​ 2026

Enjoy intimate, candlelit concerts with live orchestral music, featuring rock, Broadway, and opera performances in a magical historic setting.

Where: Toronto Reference Library (789 Yonge St, Toronto)

When: January 31st-February 1st, 2026 (10 am-5 pm)

Price:  $25‍

Category: Family-friendly

Click here for the website.

13. DesignTO

DesignTO Festival is a 10-day design celebration with 100+ events and exhibitions across Toronto, focusing on sustainability, creativity, and community. Most events are free, with some requiring RSVP or tickets.

Where: 2 Bloor St W, Toronto

When: January 23rd - February 1st, 2026 (times vary per event/exhibit)

Price:  RSVP‍

Category: Family-friendly

Click here for the website.

14. Design Collection at Stackt

Experience 10 days of immersive art and design, featuring interactive workshops, sculptural installations, and creative showcases that explore culture, community, and the human experience.

Where: Stackt Market (28 Bathurst St)‍

When: January 24th - 25th, 2026 (12 pm - 8 pm)

Price:  Free admission‍

Category: Family-friendly

Click here for the website.‍