Like many major North American cities, Toronto has a past marked by industriousness, innovation and colonialism. And it bears that history – the good and the bad – in several landmarks and historical sites.

Beginning in 1793 with the unfortunate Toronto Purchase (when the British essentially tricked the Mississaugas First Nations out of their land), the city burgeoned into an epicentre for Canadian industry, thought and politics. Early Torontonians erected impressive buildings, sprawling factory complexes, towering civic buildings and modest homesteads. They poured their hopes and ambitions into the land. And, in their own way, they were instrumental in making Toronto the thriving, thrumming, diverse metropolis it is today.

In this blog post, we at Harvey Kalles are paying tribute to that storied history. As Toronto’s preeminent real estate professionals, we obviously love this city. We love its modern features and cutting-edge spirit. But we also love its time-worn treasures. Join us below as we list our favourite Toronto landmarks, historical buildings and important pieces of Toronto architecture.

The Gooderham Building

Jutting out from the cross-section of Wellington and Front, The Gooderham Building (AKA the “Flatiron Building”) looms large over downtown Toronto. The CN Tower may have a height advantage, but the Gooderham Building has the advantage of being “in your face,” wedging its way into countless selfies and Toronto postcards.

Finished in 1892, the building got its nickname as The Flatiron for its unique wedge-like shape – a trendy architectural feature back in those times. But its real name, Gooderham, comes from the person who built it. William Gooderham devised the monumental red-brick building to serve as offices for his company Gooderham and Worts, a distillery that kept Canada flush with whiskeys and other spirits. (Later, during the World Wars, the distillery would pivot toward producing anti-freeze, but that’s a historical fact for another article).

Recently restored, the building is a treasure of the contemporary St. Lawrence neighbourhood, and an obligatory stop on any and all architectural tours in Toronto. But ol’ Gooderham’s story doesn’t end there. The guy also gave us our next stop on this roundup of Toronto landmarks.

The Distillery District

To some, it’s Toronto’s ideal first-date spot. To others, it represents an annual Christmas tradition. And for many Torontonians, it’s a little escape from the modern hustle of the SIx, a frozen-in-time snapshot of the way things used to be.

The Distillery District is one of our favourite things about Toronto. Ambling through its cobbled lanes, you’re hit with the sights of brilliantly restored brick and Victorian industrial architecture – all thanks to some serious revitalization efforts back in the early aughts. The district was originally created by William Gooderham (him again!) and served as his company’s central distillery site. Now, the historic landmark is home to countless boutiques, restaurants, cafes and art spaces.

If you want to live close to the Distillery District (and why wouldn’t you), connect with one of our top realtors about homes in the surrounding Corktown, Moss Park or Riverside areas. And if you want to learn more about landmarks like the Distillery District, you can peruse our resource on the topic – linked directly to the left.

Evergreen Brickworks

While The Distillery District gets the lion’s share of attention, it isn’t the only revitalized industrial landmark in the city. Head a few kilometers north and you’ll hit Evergreen Brickworks, an expansive historical site that serves as a lesson in classic Toronto ingenuity.

Once the site of brick manufacturing (as you might tell from the name), the area fell into disuse as the industrial revolution dwindled. And, like many other sites in the city, it laid dormant for many decades – occasionally used for raves in the 90s, but little else. Then, some enterprising people swooped in to flip the script on Evergreen Brickworks. With help from the city, they turned it into an ecological preservation site – featuring farmer’s markets, local food festivals, a garden store and educational programs.

Is there anything more Toronto than that: taking a complex once defined by smoggy smokestacks and industrial runoff, and turning it into a modern example of ecological perseverance? You love to see it.

Casa Loma

“Casa Loma” sounds like it belongs in a historic Mexican town somewhere. But it’s 100% Toronto. Unlike the scrappy ecocentrism of Evergreen Brickworks or the quaint pedestrianism of the Distillery District, this one is all about glitz and glamour.

Styled after a gothic castle in 1914, Casa Loma was once the mansion of ultra-wealthy financier Sir Henry Pellatt. He had stables, servant quarters and the whole nine yards. But when Pellatt hit hard times financially, he was forced to surrender the massive estate – and the rest is history. Now, Casa Loma, having undergone tens of millions of dollars in restorations, serves as a ritzy event space, hospitality venue and buttoned-down party destination.

It’s one of the true gems of Midtown Toronto, and a fantastic launchpad to discover the history of neighbourhoods in Toronto.

The ROM

Sometimes, we forget that the ROM is old. Maybe it’s because the building now features a jagged crystalline structure shooting out of it, a recent update created by the famous architect Daniel Libeskind.

But the Royal Ontario Museum dates back to 1912, its history still evident in the original edifice and interior rooms. Aside from being one of the Toronto museums to visit if you have a spare afternoon, the building encapsulates what we admire about this city. It is old and new, traditional and modern, old-fashioned yet daring. It’s also home to some incredibly cool dinosaur reconstructions, making it an engaging activity for Toronto families.

When you’re smack dab in the middle of Dundas Square, surrounded by neon signs, skyscrapers and video billboards, it can be hard to think of Toronto as old. But as these historical places in Toronto demonstrate, the city is steeped in its own past. And whether you’re looking to claim some of that history with a heritage home, or keen to put down roots in a historically rich neighbourhood, the expert realtors at Harvey Kalles can help you find your dream home in Toronto.