Street Walking: Old Toronto

Due to winter’s final kick, I haven’t been out shooting as much as I would have liked. But, this past Thursday, the first day of spring, though it was cold, grey and periodically snowy, I decided to take my camera along for a lunchtime stroll. I decided to head east and venture into the most beautiful part of Toronto… Old Toronto.

Established in 1793 as York, and declared the new home of the capital of Upper Canada, and later named Old Toronto, the area spans the streets in lower East side of Toronto and borders the glassy and fast-paced financial district, that can be seen in the background of some of the photos below.

The neighbourhood’s most prominent, and famous, landmark is the Gooderham Flatiron Building. Much smaller than it’s much grander cousin in New York, the Flatiron Building is a beautiful red-brick building that has stood at the centre of Toronto since 1892.

flatironflatiron back side

A walk through the streets of Old Toronto is like suddenly stepping back into the mid-19th century. The neighbourhood was devastated by a massive fire in 1904, but the buildings and streets that remain boast gorgeous architecture and detail that we will likely never see again.

front st shops closeup front st shop windows

The buildings are now home to restaurants, shops and office spaces, but it’s an awe inspiring stroll through our country’s past.

front st shops flatiron looking up p.j. o'brien




  1. It’s a shame that they don’t build in that old style anymore. It looks way better than the soulless glass & concrete buildings that they raise all over the world these days.
    I’ve seen the Flatiron building in New York, but I’ve never been to Canada. Hopefully I can visit some day in the future.

    1. I completely agree. I am always so drawn to the older stuff, and that’s why I felt like I was in heaven while on my last visit to Europe. Of course there is the same new expansion going on there, but Europe has soooo much more history to explore than we do.

      You should visit someday. Though I like some aspects of Toronto, you just can’t beat the Ocean vistas on our East and West coast, and the HUGE mountains out West. It’s all breathtaking.

  2. I just came here from Leanne Cole’s blog….I am from Toronto and this particular post took me on a GREAT trip down memory lane. It’s my old stomping grounds, having worked in the financial district for over 30 year. I have recently picked up my camera again after a many year hiatus. Thank you for the inspiration!

    1. Wow, that’s so great to hear. I’m glad you liked the post. This is one of my favorite areas in the city. Are you still in Toronto?

      My dad had a studio at Sherbourn & Adelaide in the early 80s, and the place has changed dramatically since then. It sounds crazy now, but I used to wander the streets alone at the age of five or six while my dad worked. Wouldn’t happen now.

      1. I know the area well. 5 years ago my husband & I moved east to Prince Edward County – he is now retired and I am semi-retired.
        I worked at Bay & Adelaide in the historic Canada Perm building for years and years. I miss that part of the city.
        Great shot of ‘rush hour’ too, BTW – I lived that life…now my commute is 40 minutes on country roads. My biggest traffic slow down is usually a tractor! 🙂

      2. Oh wow, you are living the dream… or, at least my dream. I love PE county. We rented a cottage there about six years ago. Some big old converted barn. It was fun.

        We’re moving to Ottawa in a couple of months, so it’ll be a nice change, and I expect my photography to change along with it to some degree.

      3. I will look forward to your new posts then…
        My photos are mostly of the county…I love this area.

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