Toronto Blue Jays – Home Games
Dates: Various dates throughout May 2026
Location: Rogers Centre, Toronto
Baseball season is in full swing by May, making it a perfect time to catch a Toronto Blue Jays game. With warmer weather, the stadium atmosphere becomes even more lively—especially when the roof is open. Expect big crowds, great energy, and classic ballpark food.
Hot Docs Canadian International Documentary Festival (Final days)
Dates: Until May 3, 2026
Location: Various venues, Toronto
Catch the final screenings of Hot Docs Canadian International Documentary Festival, North America’s largest documentary festival. A great opportunity to see impactful storytelling and attend filmmaker Q&As before the festival wraps.
Cherry Blossom Season at High Park (Peak Bloom)
Date: Early May 2026 (weather dependent)
Location: High Park
Early May is typically peak bloom for Toronto’s famous Sakura trees. Visitors flock to High Park for scenic walks under soft pink blossoms—one of the city’s most photogenic spring experiences.
Victoria Day Fireworks
Dates: May 18, 2026 (Monday)
Location: Ashbridge’s Bay Park and other locations
Celebrate Victoria Day with fireworks displays across the city. Ashbridge’s Bay hosts one of the largest shows, drawing crowds for an evening of lakeside festivities.
Contact Photography Festival 2026
Dates: Throughout May 2026
Location: Various galleries across Toronto
The Scotiabank CONTACT Photography Festival transforms the city into a massive photography gallery. Expect exhibitions in museums, public spaces, and outdoor installations featuring both local and international artists.
Doors Open Toronto
Dates: May 23–24, 2026 (expected)
Location: Various historic and cultural sites across Toronto
Explore the city’s architecture and hidden spaces during Doors Open Toronto. Buildings normally closed to the public—historic sites, cultural institutions, and unique spaces—open their doors for free.
Toronto FC – MLS Matches
Dates: Various dates throughout May 2026
Location: BMO Field
Catch Toronto FC in action as the MLS season heats up. Expect passionate fans, energetic chants, and a vibrant soccer atmosphere by the lake.
Spring Food Festivals & Patio Season Kickoff
Dates: Throughout May 2026
Location: Various locations across Toronto
May is when patio season truly comes alive. From food truck festivals to neighbourhood street eats, Toronto’s culinary scene shifts outdoors with lively crowds, fresh spring menus, and longer evenings.
Toronto Islands Opening Season
Dates: Throughout May 2026
Location: Toronto Islands
Ferry season picks up as visitors head to the islands for biking, picnics, and skyline views. A perfect spring escape just minutes from downtown.
VISIT OUR CALENDAR PARTNERS’ EVENTS IF YOU FIND YOURSELF IN THE CITIES BELOW:
New York
Washington DC
Miami
San Francisco
Los Angeles
Orange County
Chicago
Greenwich
Denver
Naples
Taho, Reno-NV
Sacramento
The Hamptons, NY
Atlanta
Tampa Bay
Park City
Sarasota
Darien, CT
Dallas
