Before Toronto Had a Skyline, It Had a Windmill: the Gooderham Building

Lately, when walking through Old Town Toronto, attention is drawn to the Gooderham Building. Even now, wrapped in restoration scaffolding at the corner of Wellington and Church, it still possesses a certain “postcard” quality.

The beauty of the Flatiron Building isn’t just in its red brick or its famous silhouette. It lies in the layers of history that connect this iconic office tower to a massive, seven-storey windmill that once dominated Toronto’s 19th-century shoreline.

A Landmark Before the Skyline

In the 1830s, long before the CN Tower or the financial district’s glass spires, Toronto, then the young town of York, had a very different navigational beacon. James Worts and William Gooderham, brothers-in-law newly arrived from England, built a towering windmill on the waterfront to grind grain. It was the tallest structure around, so prominent that residents used it as a compass.

A Family Tragedy Behind an Industrial Empire

The history of this landmark is also a deeply personal one. The partnership took a tragic turn when Worts’s wife, who was also Gooderham’s sister, died during childbirth. Consumed by grief, Worts took his own life by jumping into the mill’s well.

Left to lead alone, Gooderham showed a remarkable, if pragmatic, resilience. He realized that the leftover grain from the milling process could be repurposed to produce alcohol. This pivot transformed a simple mill into the Gooderham & Worts distillery, which by the late 1800s had become the largest in the world, producing over two million gallons of whisky annually. Today, we know the remnants of this industrial empire as the Distillery District.

The Windmill’s Long Shadow Over Toronto

In 1892, George Gooderham (William’s son) commissioned the Flatiron Building we see today. From his office at the tip of the “flatiron,” he could look out over the harbor and keep an eye on the family’s distillery operations.

There’s a fascinating historical footnote in a map illustrated for the 100th anniversary of Toronto’s incorporation in 1934. E.G.A. Foster imagined what the city might have looked like a century earlier. In the corner of that map stands a lone, tall windmill. It’s no longer there, but its legacy is.

The Flatiron Building isn’t just a pretty Victorian tower; it reads as the spiritual successor to that first windmill—a symbol of the ambition, tragedy, and transformation that built Toronto.

The next time the scaffolding-covered Flatiron Building comes into view, it’s worth looking past the bricks. What appears is the latest layer of a story that began with wind and water.

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