Kensington Market

Let’s start with the city’s quintessentially hip artistic neighbourhood, which should rightfully be cordoned off for pedestrians only (and, in practice, is not a place you want to drive anyway). Kensington’s rich and diverse history dates back over a century, and includes waves of Jewish, Chinese, Latino, African and Southeast Asian immigration. Today, you’ll find brightly painted cafes and vintage clothing shops packed into duplex row houses next to synagogues, Chinese associations, art galleries and ethnic supermarkets. Raising rent has forced the closure of a few classic mainstays, but you can brave the lines to find good eats at Rasta Pasta (a small fusion Jamaican-Italian joint with excellent jerk chicken), Wanda’s Pie in the Sky (a beautiful little bakery with massive and heavenly croissants), Seven Lives (a small taco shop, always packed) and Pow-Wow Cafe (modernized Native American food with world-class frybread).

Originally named The Kensington Market Festival of Lights in 1988, this annual tradition has continued into the modern day as an artistic celebration of art, street performance, and finding warmth in the chilly temperatures. Every year on December 21st, an artistic parade encompassing warmth and light takes place in Toronto’s most eclectic neighborhood: Kensington Market. The parade honors the cultural significance of the winter solstice as an ancient cardinal point. Complete with handmade lanterns, giant puppets, fire breathers, stilts, theatrical performances, and more, this fantastic night of celebration is one of the most fascinating, time-honored Toronto events happening in the wintertime. While in the area, check out Cold Tea, one of our favorite snack bars in Toronto.