Toronto in September

May through October gives you Toronto at its best. The city shakes off winter's grip in May, with temperatures hitting 20°C and patios reopening across the city. This is when Torontonians remember how to smile again. June and July bring festival season. The Toronto International Film Festival takes over the city in September, but summer brings Caribana (now called the Toronto Caribbean Carnival), Pride Month celebrations, and endless street festivals. Expect crowds and higher hotel prices, but the energy is infectious. August gets humid – we're talking 30°C with humidity that makes it feel like 40°C. But this is prime time for the Toronto Islands, outdoor concerts at the Harbourfront Centre, and rooftop bars across King West. September and October offer the sweet spot. Temperatures drop to a comfortable 15-20°C, fall colors hit High Park and the Don Valley, and you can actually get restaurant reservations again. TIFF brings celebrities and cinema lovers from around the world. Winter (November through April) tests your resolve. January temperatures drop to -10°C, with wind chills that'll freeze your face off. But hotel rates plummet, you'll have museums to yourself, and there's something magical about skating at Nathan Phillips Square with the CN Tower looming overhead. Avoid the last week of December through early January – everything shuts down, transit runs on reduced schedules, and even Torontonians flee to warmer places.