Long before Bob was walking the streets of Toronto with a Sony camera around his neck, someone else in the family was already doing the same thing.
Bob’s great-great-grandfather.
Back in the late 1800s, when Toronto was a city of cobblestone streets, horse-drawn wagons, church towers, and factory smoke, he was already out documenting everyday life.
His camera was nothing like the ones we use today.
It was a large wooden bellows camera mounted on a heavy tripod. The kind where the photographer had to carefully set up the shot, duck under a cloth, and focus the image on a glass plate.
Photography was slow work back then.
But Bob’s great-great-grandfather loved the streets.
Photographing Life on the Streets
While many photographers of that era worked inside studios taking formal portraits, Bob’s ancestor preferred to photograph real life outside.
He captured scenes of:
Families walking through the city
Workers heading to factories
Horse-drawn wagons rattling down cobblestone streets
Children stopping to watch the strange camera on the tripod
In many ways, he was doing what we now call street photography, long before the term even existed.
He understood something that Bob still believes today:
The streets tell the story of a city.
Exploring the Don River
Family stories say he sometimes traveled through the city using the Don River, paddling a small canoe with his camera and tripod carefully packed beside him.
When he found an interesting place—a bridge, a busy street corner, or a market—he would pull ashore and set up the camera.
People would gather around to watch.
And sometimes, without even realizing it, they became part of the scene.
After all, photography was still something of a mystery back then.
A Family Tradition of Street Photography
Looking at the old stories and images, Bob sometimes thinks that street photography might run in the family.
His great-great-grandfather walked the same streets.
He photographed everyday life.
He waited for moments to unfold.
He recorded the small details that make a city what it is.
The equipment may be different today.
The cameras are smaller.
The photos are digital.
And instead of paddling a canoe, Bob often rides the TTC to reach different parts of Toronto.
But the idea is still the same.
Walk the streets.
Watch people.
Wait for life to happen.
And take the photograph.
Maybe Bob didn’t start street photography in Toronto.
Maybe he’s just continuing something that started in the family more than a century ago.


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