Toronto's biggest 2026 events, in chronological order: 1. Winterlicious (Jan 30–Feb 12) — discounted prix-fixe menus at restaurants city-wide; 2. Canadian International AutoShow (Feb 13–22) at Metro Toronto Convention Centre (255 Front St. W.); 3. Cardi B concert (Mar 30) at Scotiabank Arena; 4. Doors Open Toronto (May 23–24) — free access to landmark buildings; 5. Luke Combs concerts (Jun 5–6) at Rogers Stadium; 6. Pride Toronto (Jun 25–28) — Canada's largest festival and the world's second-largest Pride celebration; 7. Caribana (Jul 30–Aug 3) — North America's biggest Caribbean carnival with over 1 million attendees; 8. Olivia Dean: The Art of Loving Live (Aug 5) at Scotiabank Arena; 9. Ed Sheeran concert (Aug 20) at Rogers Centre; 10. The CNE (Aug 21–Sep 7) at Exhibition Place; 11. AC/DC concert (Sep 16) at Rogers Stadium; 12. Nuit Blanche (Oct 3) — the city-wide all-night art festival.