I was out for dinner last night on Ossington (here in Toronto). Afterwards, my business partner Rick and I walked the street for a bit. It was a beautiful evening. Every restaurant had their doors and windows open. All of the patios were full, many with the kind of awnings that I love from Paris. And in between these patios were endless options for beautiful window shopping. So during our walk, we couldn't help but say to each other, "man, what an awesome street."
Our line of thinking then went here: How did this ~600-meter stretch of street between Queen and Dundas become one of the coolest retail streets in the city? As you might expect, it follows the typical urban trajectory. It was a seedy street with cheap(er) rents. Then the artists and creatives started moving in, along with OG dive bars like Sweaty Betty's. And then the city implemented a brief moratorium on bars and restaurants because things were getting a bit too fun.
I also think it's fair to call Ossington's rise as being a spillover from Queen Street West. As rents rose on Queen, Ossington became a natural outlet. It was in the right location, and it already had a commercially-oriented and fine-grained ground plane, meaning the buildings could be easily repurposed for galleries, bars, restaurants, and whatever else. This is also why the strip just dies north of Dundas — there are no more suitable buildings.





