Things To Do in Toronto This Week (October 19–25, 2026)
The third week of October 2026 brings an action-packed schedule of major league sports, world-class comedy specials, indie and folk concerts, and immersive autumn events to Toronto. Whether you want to catch NHL hockey and NBA basketball, laugh out loud with Dave Chappelle, or enjoy a live show at Massey Hall, here are the top things to do across the city this week from October 19 to 25, 2026.
Editor’s Note: Ticket availability, event schedules, and door times are subject to change. Check official venue websites and ticketing platforms before heading out.
THINGS TO DO IN TORONTO THIS WEEK
Toronto Maple Leafs vs. San Jose Sharks
- Catch early-season NHL action as the Maple Leafs return home to host the San Jose Sharks.
- Date: Monday, October 19, 2026 at 7:30 p.m.
- Location: Scotiabank Arena, 40 Bay St., Toronto
- Cost: Ticketed
Toronto Raptors vs. Chicago Bulls
- Basketball season tips off as the Raptors host the Chicago Bulls for an exciting regular-season home game at the arena.
- Date: Tuesday, October 21, 2026 at 7:30 p.m.
- Location: Scotiabank Arena, 40 Bay St., Toronto
- Cost: Ticketed
Toronto Maple Leafs vs. New York Rangers
- Stay for another thrilling home matchup as the Maple Leafs take on the New York Rangers under the bright arena lights.
- Date: Thursday, October 23, 2026 at 7:00 p.m.
- Location: Scotiabank Arena, 40 Bay St., Toronto
- Cost: Ticketed
Dave Chappelle: Karmageddon
- World-renowned comedian Dave Chappelle brings his highly anticipated Karmageddon tour to the city for a massive Friday night comedy event.
- Date: Friday, October 23, 2026 at 7:30 p.m.
- Location: Scotiabank Arena, 40 Bay St., Toronto
- Cost: Ticketed
The Tallest Man on Earth + Gwenifer Raymond
- Enjoy an intimate evening of brilliant indie-folk and intricate acoustic guitar stylings live on stage.
- Date: Friday, October 23, 2026
- Location: Massey Hall, 178 Victoria St., Toronto
- Cost: Ticketed
Toronto Argonauts vs. Montreal Alouettes
- Experience high-stakes Canadian Football League action as the Argonauts battle the Montreal Alouettes on the turf.
- Date: Friday, October 23, 2026 at 7:00 p.m.
- Location: BMO Field, Exhibition Place, Toronto
- Cost: Ticketed
Jonas Brothers: The Running Up Tour
- Pop icons the Jonas Brothers take over the downtown arena with their hit-filled stadium tour.
- Date: Saturday, October 24, 2026 at 7:30 p.m.
- Location: Scotiabank Arena, 40 Bay St., Toronto
- Cost: Ticketed
Dream Serenade
- Attend the heartfelt annual benefit concert bringing together incredible musical guests and community artists for a wonderful cause.
- Date: Saturday, October 24, 2026
- Location: Massey Hall, 178 Victoria St., Toronto
- Cost: Ticketed
Fall for Dance North
- Catch the final weekend performances of this celebrated annual festival featuring diverse, world-class contemporary and classical dance troupes.
- Dates: Through Sunday, October 25, 2026
- Location: Various performance venues across Toronto
- Cost: Ticketed
John Summit: CTRL ESCAPE Album Tour
- Electronic music star John Summit closes out the weekend with an electric arena performance supporting his latest album tour.
- Date: Sunday, October 25, 2026 at 7:00 p.m.
- Location: Scotiabank Arena, 40 Bay St., Toronto
- Cost: Ticketed
Legends of Horror at Casa Loma
- Explore Toronto’s historic castle transformed into a theatrical Halloween walk-through experience with dramatic lighting, live actors, and spooky set pieces.
- Dates: Throughout October 2026
- Location: Casa Loma, 1 Austin Terrace, Toronto
- Cost: Ticketed
Practical Planning Notes
Mid-to-late October in Toronto brings lively autumn crowds and multiple concurrent arena events, particularly around the downtown core near Scotiabank Arena and Massey Hall. Using the TTC is strongly recommended to avoid heavy traffic and limited parking during major game nights and concert double-headers. Be sure to secure your tickets and check venue entry policies in advance.
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