This weekend I went on a long bike ride across the city with my friend Ev (who, by the way, just recently got married. Congratulations again to you both!). This was not a ride to pump my feeble Strava stats, but a ride to see and explore our wonderful city. And once again I was reminded that one of the easiest ways to fall in love with Toronto is to get on a bike and ride across it. Biking offers the best of both worlds: it's both fast and efficient, and it's granular. You can easily slow-ride through smaller spaces or quickly get off and walk them.

If I'm ever in the mood to elicit a shitstorm of negative reactions, all I have to do is go on Twitter and tweet something pithy about how much I love Toronto. I don't know why so many people seem to react like this, but I genuinely feel this way about our city. City-building is a slow process, but a spring ride after a cold winter will reveal to you all of the projects we've been working on quietly in the background: new streets, new mid-block connections, new public spaces, new businesses, and beautiful architecture.

Of course, not all of it is exceptional. At one point, Ev and I came across two newly constructed courtyards in the middle of large developments that will remain unnamed. One was beautiful and held the promise of businesses and F&B lining its edges, while the other was empty and grim looking. We then turned to each other and said: "Isn't it amazing how different these not-so-different courtyards are?"

But objectively, there's so much that we are getting right. New streets are now subdividing formerly large, unwalkable blocks. Existing neighbourhoods are growing, adding sustained urban vibrancy. New megaparks, like Biidaasige Park in the Port Lands, have already become fantastic, well-used spaces, setting the stage for new urban neighbourhoods to crop up all along their edges. And many of our new buildings are, quite frankly, gorgeous.

Most importantly, though, people are using these spaces — a lot. They're filling sidewalks, hanging out on patios, and cycling on new bike lanes. It's easy to focus on the things that Toronto isn't or doesn't have, just like it's personally easy to focus on what you may not be or have. Bringing positivity doesn't mean ignoring the challenges that our city is facing, but being grateful for everything we are achieving is a great way to reframe our perspectives toward an abundance mindset.

If you're looking for an easy way to do that, try getting on a bike on a beautiful sunny day.

Back in 2016, the New York Times published an article where it cited that at least 40% of the buildings in Manhattan could not be built today because they don't conform to the city's zoning code for one or more reasons. These reasons might include too much density (FSI / FAR), too many units, inadequate setback requirements, or something else.

This is a tricky number to estimate as most cities don't track it, but I asked Gemini and Claude to try for Toronto, and they returned 70-80% and 45-55%, respectively. Claude's estimate seems to be lower because it assumed that all of the subdivided single-family houses are now legal because of the new multiplex permissions.

I don't know about that, but the point is that there's a meaningful, non-zero quantity of buildings in our cities that we decided to make illegal, and generally difficult, or impossible to build again. The thing that I'm most interested in dissecting is: why?

Here's one way to look at it. My follow-up question to both AI models was: What percentage of buildings within a Heritage Conservation District would you say are illegal to build in Toronto today? And both models agreed that the number is 90%+, and probably very close to 100%.

Heritage Conservation Districts are a way of saying "these buildings and this urbanism is so good, that it's worth preserving through extra layers of planning protection." But at the same time, our other policies say, "you shall never build anything like this ever again." It's incoherent.

A more coherent approach might be to call them Heritage Renewal Districts where we instead codify the following: "this district is now illegal based on our current planning rules and so the objective is to tear it all down and replace it with new, approved buildings." Sounds like blasphemy, doesn't it? So then why block more of it?

If it's worth conserving, then it's worth building more of. What ought to be obvious is that we need more rather than less planning flexibility, and we need to legalize the things that have been proven to work, like traditional fine-grained patterns of city-building.

Cover photo by Ayman Hallak on Unsplash

Toronto, by and large, does not like car-free urban streets. I mean, we have very few of them. Let's try and name them. The most notable would be the Distillery District. Next to this would perhaps be the intersection of Gould Street & Victoria Street on TMU's campus. Then there's Willcocks Commons at the University of Toronto, though it's not the prettiest.

After this, I can only think of small, unremarkable or temporary ones. I'm not counting seasonal closures. Technically, the Toronto Islands are the largest car-free community in North America, but I wouldn't call this urban. So I'm now at a loss. If I've missed any noteworthy ones, I would be happy to be corrected.

This concise list makes the recently revealed masterplan for the island formerly known as Villiers — now called Ookwemin Minising (or OM) — all the more exciting. The 16-block plan now includes a 760-metre-long, fully pedestrianized public space called Centre Commons. It runs east-west in the site plan below, and is intersected by a north-south street called The Sandbar Trail.

As designed, Centre Commons is expected to be the longest car-free street in the city and look something like this:

This is the space in between the buildings. Equally important is the fact that the new masterplan unlocks a 27% increase in finer-grained density, without compromising on the quality or quantity of public space on the island. This is a major improvement over the previous masterplan, which had all the hallmarks of bland pseudo-urbanism. Meaning, it was supposed to be urban, but it wasn't actually.

I love the above massing diagram because it feels like a real, organic city, as opposed to just a series of repeating towers on podiums. It has a variety of scales and a more fine-grained urban pattern. This, as we have talked about, is notoriously difficult to achieve in new master-planned communities. But it is possible: loop transit through the island, lower the parking requirements, and give developers the freedom to build.

The design team includes SLA of Copenhagen (landscape architects), Trophic (Indigenous-owned landscape architects), GHD (prime consultant and technical lead) and Allies and Morrison of London (architectural lead). And when built out, OM is expected to support approximately 12,000 new homes (including 3,000 affordable homes) and 2,900 new jobs.

I say we build it.

Cover photo by Allies and Morrison

Aerial image from Waterfront Toronto

Centre Commons rendering by Norm Li via SLA

Area plan and massing diagram by SLA