I came across this tweet the other night showing Toronto's Yonge Street.

In the foreground are small, two-storey main street—type buildings. And behind them are tall buildings. This is very Toronto. What you're seeing here is a condition that occurs all around the city. Though in many ways, it feels counterintuitive. I mean, shouldn't the tallest buildings be right on the main street?

In my opinion, this condition is happening for at least two reasons.

The first is that Toronto's historic main streets tend to have a fine-grained lot fabric, which means they're more challenging to assemble for larger developments. Assemblies are a complex art, and they get exponentially more difficult the more property owners and feuding siblings you add into the mix. So the path of least resistant is larger and chunkier sites.

The second reason has to do with context. We tend to want to preserve the feel of our historic main streets. One Delisle is an example of this. The podium of the tower is scaled to exactly match what was there before — an Art Deco-style facade from the 20s that will return to the site.

However, we didn't have this same constraint on its other elevation (Delisle Avenue) and so we fought not to have your typical podium + setback tower. Instead, we wanted a street level experience that had more presence and urban grandeur.

This, to me, is an important distinction to consider. Are we setting height back because of history and context? Both of which are important. Or are we setting it back because we're pretending to still be a provincial Anglo-Protestant town? Sometimes it seems like it's because of the latter.

Cover photo by Yi Wei on Unsplash

“Make no little plans. They have no magic to stir men’s blood and probably themselves will not be realized. Make big plans; aim high in hope and work, remembering that a noble, logical diagram once recorded will never die, but long after we are gone will be a living thing, asserting itself with ever-growing insistency. Remember that our sons and grandsons are going to do things that would stagger us. Let your watchword be order and your beacon beauty. Think big.”

-Daniel Burnham, Chicago architect. (1846-1912)

I’m a big fan of Chicago. Having now visited the city, I can say that everyone was right when they told me that I was going to love it. It has great art and architecture, great food (with some of the largest portions I’ve ever seen), great nightlife, and great people. 

But I don’t want to talk about any of these things today. Instead, I want to talk about something much more specific that stood out to me last weekend: Chicago’s relationship to both the water and the street.

While Chicago and my hometown of Toronto share many similarities– including being situated on a Great Lake and having rivers flow through the middle of them–the relationship to these bodies of water is remarkably different. Here is a photo of people kayaking in the Chicago River on a Friday afternoon:

What impressed me about Chicago is how intimate and urban the relationship is with the lake and its rivers. If you look at the photo above, you’ll see that many of the buildings are built right up against the river, but that there’s space allocated for riverwalks, patios, and so on. It’s all about engaging and connecting with the water.

Toronto on the other hand, is only recently starting to reacquaint itself with its bodies of water. We spent much of the second half of the 20th century with our back turned to the lake and without a strong urban connection to the Don River. And if I had to guess why it’s because we built highways along them.

We built the Gardiner Expressway adjacent to Lake Ontario and we built the Don Valley Parkway adjacent to the Don River. This fundamentally changed our orientation and largely precluded us, I think, from creating the same kind of waterside urbanity offered in Chicago.

As an example, consider that in the first half of the 20th century, Toronto’s Parkdale neighborhood – which today still has a questionable reputation – was actually an affluent and desirable waterfront community filled with beautiful Victorian mansions. It was well connected to the waterfront, and so the area flourished. Here’s what Sunnyside Pavilion used to look like:

But then in the 1950s we built the Gardiner Expressway, disconnecting Parkdale from the lakefront and destroying many of its amenities, such as the Sunnyside Amusement Park. In turn, the rich people left and their large Victorian mansions got chopped up into rooming houses and other rental housing stock. And in my view, Parkdale still hasn’t fully recovered from this. 

Highways are divisive. There’s no question.

So unless you can afford to bury them, it comes down to trade offs: Do you want to make it easier for people to drive in from the suburbs or do you want a truly spectacular water or riverfront? In the 1950s we chose the former. But even still today, the thought of tearing down–even a portion of the Gardiner Expressway–is fraught with opposition. I guess not much has changed.

The second way that Chicago impressed me is through the relationship that many of its buildings hold to the street. They come down to ground level with authority and with great retail presence, and often make no amends about their mass and impressiveness. This frames the street and creates a level of urbanity that isn’t always found in Toronto – particularly outside of the downtown core.

In Toronto, the trend today is towards street level podiums, significant setbacks, and delicate point towers that minimize the impact of their height and allow for natural light to reach street level. It’s well-intentioned and perfectly appropriate in many urban settings. But sometimes you need a little urban assertiveness. Sometimes you want to impress and impose. And Chicago does that.

What I’m getting at is that Chicago architect Daniel Burnham was on to something. He famously advocated for man (that was the era) to think big. Make no little plans, he said. And it’s admirable advice. Toronto is going through a tremendous transformation right now. We’re North America’s boomtown, which is a title that Chicago would have held at one point.

But as we build for the future, let’s remember that, long after we’re gone, we’re going to be judged based on the plans we are making today. So why not make them big ones.

I came across this tweet the other night showing Toronto's Yonge Street.

In the foreground are small, two-storey main street—type buildings. And behind them are tall buildings. This is very Toronto. What you're seeing here is a condition that occurs all around the city. Though in many ways, it feels counterintuitive. I mean, shouldn't the tallest buildings be right on the main street?

In my opinion, this condition is happening for at least two reasons.

The first is that Toronto's historic main streets tend to have a fine-grained lot fabric, which means they're more challenging to assemble for larger developments. Assemblies are a complex art, and they get exponentially more difficult the more property owners and feuding siblings you add into the mix. So the path of least resistant is larger and chunkier sites.

The second reason has to do with context. We tend to want to preserve the feel of our historic main streets. One Delisle is an example of this. The podium of the tower is scaled to exactly match what was there before — an Art Deco-style facade from the 20s that will return to the site.

However, we didn't have this same constraint on its other elevation (Delisle Avenue) and so we fought not to have your typical podium + setback tower. Instead, we wanted a street level experience that had more presence and urban grandeur.

This, to me, is an important distinction to consider. Are we setting height back because of history and context? Both of which are important. Or are we setting it back because we're pretending to still be a provincial Anglo-Protestant town? Sometimes it seems like it's because of the latter.

Cover photo by Yi Wei on Unsplash

“Make no little plans. They have no magic to stir men’s blood and probably themselves will not be realized. Make big plans; aim high in hope and work, remembering that a noble, logical diagram once recorded will never die, but long after we are gone will be a living thing, asserting itself with ever-growing insistency. Remember that our sons and grandsons are going to do things that would stagger us. Let your watchword be order and your beacon beauty. Think big.”

-Daniel Burnham, Chicago architect. (1846-1912)

I’m a big fan of Chicago. Having now visited the city, I can say that everyone was right when they told me that I was going to love it. It has great art and architecture, great food (with some of the largest portions I’ve ever seen), great nightlife, and great people. 

But I don’t want to talk about any of these things today. Instead, I want to talk about something much more specific that stood out to me last weekend: Chicago’s relationship to both the water and the street.

While Chicago and my hometown of Toronto share many similarities– including being situated on a Great Lake and having rivers flow through the middle of them–the relationship to these bodies of water is remarkably different. Here is a photo of people kayaking in the Chicago River on a Friday afternoon:

What impressed me about Chicago is how intimate and urban the relationship is with the lake and its rivers. If you look at the photo above, you’ll see that many of the buildings are built right up against the river, but that there’s space allocated for riverwalks, patios, and so on. It’s all about engaging and connecting with the water.

Toronto on the other hand, is only recently starting to reacquaint itself with its bodies of water. We spent much of the second half of the 20th century with our back turned to the lake and without a strong urban connection to the Don River. And if I had to guess why it’s because we built highways along them.

We built the Gardiner Expressway adjacent to Lake Ontario and we built the Don Valley Parkway adjacent to the Don River. This fundamentally changed our orientation and largely precluded us, I think, from creating the same kind of waterside urbanity offered in Chicago.

As an example, consider that in the first half of the 20th century, Toronto’s Parkdale neighborhood – which today still has a questionable reputation – was actually an affluent and desirable waterfront community filled with beautiful Victorian mansions. It was well connected to the waterfront, and so the area flourished. Here’s what Sunnyside Pavilion used to look like:

But then in the 1950s we built the Gardiner Expressway, disconnecting Parkdale from the lakefront and destroying many of its amenities, such as the Sunnyside Amusement Park. In turn, the rich people left and their large Victorian mansions got chopped up into rooming houses and other rental housing stock. And in my view, Parkdale still hasn’t fully recovered from this. 

Highways are divisive. There’s no question.

So unless you can afford to bury them, it comes down to trade offs: Do you want to make it easier for people to drive in from the suburbs or do you want a truly spectacular water or riverfront? In the 1950s we chose the former. But even still today, the thought of tearing down–even a portion of the Gardiner Expressway–is fraught with opposition. I guess not much has changed.

The second way that Chicago impressed me is through the relationship that many of its buildings hold to the street. They come down to ground level with authority and with great retail presence, and often make no amends about their mass and impressiveness. This frames the street and creates a level of urbanity that isn’t always found in Toronto – particularly outside of the downtown core.

In Toronto, the trend today is towards street level podiums, significant setbacks, and delicate point towers that minimize the impact of their height and allow for natural light to reach street level. It’s well-intentioned and perfectly appropriate in many urban settings. But sometimes you need a little urban assertiveness. Sometimes you want to impress and impose. And Chicago does that.

What I’m getting at is that Chicago architect Daniel Burnham was on to something. He famously advocated for man (that was the era) to think big. Make no little plans, he said. And it’s admirable advice. Toronto is going through a tremendous transformation right now. We’re North America’s boomtown, which is a title that Chicago would have held at one point.

But as we build for the future, let’s remember that, long after we’re gone, we’re going to be judged based on the plans we are making today. So why not make them big ones.