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I had two jobs in the mid-2000's where I saw a lot of Toronto addresses as part of daily work, and "Weston" was not only accepted but turned out to be the default when you entered the postal code to search the Canada Post database. Someone told me they were 90% certain it was because the Weston area had so many duplicate street names with downtown Toronto (many now changed, but not all) that Canada Post deliberately left Weston as the default in the database all along to remove any doubt among end users (like call centre agents) they had the correct place, and also the effort to sort out even those street names which were not duplicated was too much work, so whatever was Weston in 1966 was still Weston in 2006, and not Toronto.
That makes a lot of sense. The other aspect of conflict or confusion is 911 assignment. While I don't know C-K specifically, when rural areas are amalgamated, there can be repetition of numbered rural roads, Concession 3 for example, that are meaningless without the parent municipality. Where a new municipality is created, many have chosen to give these roads names which (hopefully) gives them a chance to avoid confusion or repetition. A lot of rural postal addresses still use Rural Routes, which typically are named after whichever post office the route originates from. Notwithstanding C-K is a single-tier municipality, I imagine there are still post offices in places like Tilbury, for example. We used to be an RR of the local town but CP decided to give us our own postal code using our municipal address (which caused about two years of confusion).

In urban areas, the municipal address is typically the same as the legal (deeded) address. In rural areas, not so much.
 
Though postal codes render at least a *bit* of that redundant--and old timers continued to use "Islington", "Weston", "Agincourt" et al for decades without consequence. (And the "Weston" postal address wasn't strictly bound to the former town; for instance, the Ford family on Weston Wood once *might have* used "Weston, Ontario".)

One thing w/Toronto's boroughs: it's best to think of them as analogous to NYC's boroughs, or maybe those of London as well (that is, sending something to London UK doesn't strictly mean sending something to the City of London, much as nobody sends stuff to "Manhattan, NY")
Totally. My mom grew up in Humber Heights on the Etobicoke side of the Humber, and her address (or my granda's as it were) always said, Weston. A few years ago my brother was telling some friends that my mom grew up in Weston and when I corrected him he got mad at me and mentioned their mailing address. It took some maps and Wikipedia to set him straight.
 
I imagine a lot of people still put "Weston" on their postal mail if they live on Church, John or Queen Street.

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I think an area where the boundaries have kind of disappeared is between South Swansea and Humber Bay. The Gardiner, Parks by the lake, and Condos towers. People living at Windermere/The Queensway consider themselves to live at Humber Bay, and Park Lawn/Lake Shore has much more in common with them than with Alderwood or Long Branch. I could see future riding re-draws to overlook the "natural barrier" of the Humber River, since these kind of communities have much more in common.
 
I don't think that was the reason. It is more-so that those players were born in Scarborough, not amalgamated Toronto (which didn't exist yet).

It is common practice to list the birthplace as the legal entity that existed at the time. E.g. if you look up Prince Philip on Wikipedia or elsewhere, it lists his birthplace as Kingdom of Greece, not Greece. If York Region were to amalgamate tomorrow, you would still list Marner's birthplace as Markham, for instance.
Well a definitive word on this one...


 
Until 1974 West Rouge was not part of Toronto or Scarborough, but was considered part of the township of Pickering. When Ontario County was reorganized as Durham Region that year, it was transferred to the then-borough of Scarborough under Metropolitan Toronto.

From link.

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Port Union / Rouge Hills / West Rouge

Port Union was also part of the Highland Creek community. (Although most of the buildings were across the Town Line in Pickering.) Port Union was located in the south east corner of Scarborough, at Lawrence Avenue and Port Union Road. In 1865 a post office opened in Port Union Station. Early 19th century businesses in the area included the Scarborough, Markham, and Pickering Wharf Company (est. 1847), and hotels operated by Will Hetherington and Thomas Laskey.

In the 1920s, real estate developer Cecil White & Co. purchased multiple tracts of land east of Port Union Village with intentions of creating a large community along the west bank of the Rouge River intended to become “The Venice of the North”. Although the dream was never completely realized, the name of White’s subdivision “Rouge Hills” lives on to this day as the name of the local commuter railway station.

The West Rouge community, a modern name associated with Port Union, was originally part of Pickering. Scarborough annexed the West Rouge in 1973 following several years of negotiations. There were concerns about meshing taxation and other costs to the municipality that had to be addressed following the initial annexation discussions in 1969. The West Rouge was east of the town line and west of the Rouge River containing 857 acres and a population of 3,414 at the time of annexation.
 
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Took this photo back in January 2022. The photo itself is within East York (if you look at the street signs on the right you can see the the classic “EY” style signs), but up ahead you can clearly see the street lights for the Old City of Toronto. Much of the Old Toronto/East York border seems to have identical housing typologies, but the street signs and street light changes make it clear where the former boundary is.
 
At one time, the people in Etobicoke could not put up a permanent clothesline (strung up) to dry clothes in their backyards.

This "umbrella" type was okay, because it can be collapsed and put away.
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This type was a no-no.
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View attachment 447294


Took this photo back in January 2022. The photo itself is within East York (if you look at the street signs on the right you can see the the classic “EY” style signs), but up ahead you can clearly see the street lights for the Old City of Toronto. Much of the Old Toronto/East York border seems to have identical housing typologies, but the street signs and street light changes make it clear where the former boundary is.

This picture is proof Metro Toronto was for all intents and purposes a single city.
 
The former City of York is remarkably obscure now in contrast to how common it is to hear about Scarborough, North York, and Etobicoke as geographic entities to this very day. I found that even Google Maps has had the wrong boundaries for it in the past.

However, it still has its blue and white street name signs. Its hilly geography is fairly unique, with most streets having a slope to them. Also, its residential neighbourhoods often have public staircases and walkways as interesting pedestrian connections between streets.
I also notice York has a lot of these small triplex apartments (known as the Toronto Special). It seems like these are way more common in York than the 5 other former municipalities.

 
I also notice York has a lot of these small triplex apartments (known as the Toronto Special). It seems like these are way more common in York than the 5 other former municipalities.


Excellent point. I noticed that recently as well, and it's quite interesting. Apparently, they were legal throughout most of York before amalgamation, which is quite different to Scarborough and Etobicoke's heavy emphasis on single-family-home zoning.

They generally don't make their residential streets worse in York versus similar streets in Etobicoke and Scarborough (and I would argue that they make them better by offering a more metropolitan built form and by making quality housing on quiet streets available to more people). However, they're often the properties without trees or any landscaping in the front yard due to stingy investors pinching every penny they can.

Going forward, the city needs to do everything in its power to ensure that multiplexes don't degrade streets by offering no landscaping and paved-over backyards. It's hardly a multiplex issue. The same thing happens with investor-owned single family homes as well. They often cut down the trees on the property or refuse to plant trees and pave over the backyards for parking (which is actually illegal in Toronto). It cheapens and degrades our neighbourhoods.
 
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Excellent point. I noticed that recently as well, and it's quite interesting. Apparently, they were legal throughout most of York before amalgamation, which is quite different to Scarborough and Etobicoke's heavy emphasis on single-family-home zoning.

They generally don't make their residential streets worse in York versus similar streets in Etobicoke and Scarborough (and I would argue that they make them better by offering a more metropolitan built form and by making quality housing on quiet streets available to more people). However, they're often the properties without trees or any landscaping in the front yard due to stingy investors pinching every penny they can.

Going forward, the city needs to do everything in its power to ensure that multiplexes don't degrade streets by offering no landscaping and paved-over backyards. It's hardly a multiplex issue. The same thing happens with investor-owned single family homes as well. They often cut down the trees on the property or refuse to plant trees and pave over the backyards for parking (which is actually illegal in Toronto). It cheapens and degrades our neighbourhoods.
Agree 100%!
 
Well, it's also because of the date and nature of York's development--so much of it came about as the archetypal dense and "unplanned" blue-collar suburb of the early c20, and it was also a consequence of the kinds of people doing the building, and the clientele being served, after the war. So this is the fare that "filled the gaps" which early c20 ad hoc development missed, or that which replaced the tar-paper shacks of the early ad hoc years (which were more prevalent in York than Toronto, because of less rigorous building standards), often on behalf of the new immigrant classes that were rapidly filling out the postwar city. Whereas in the kinds of postwar suburbs that were *already*, to some degree, "planned", whether the Don Mills model or the CMHC tracts before them, this kind of spontaneous "builder's vernacular" was redundant or more to the margins--and the more old-stock-Canadian (or, if you want, "white trash") blue-collar demo bought right into the single-family suburban bungalow dream that the CMHC was dishing out. The Toronto Specials were, deemed, by and large, to be for the "blue-collar newcomers"--it's just happened to be that York was an epicentre for such "newcomers", but you also find them in "newcomer-friendly" adjacent parts of Toronto and North York (yes, even a more suburbanized form thereof in 60s Downsview).
 
Was walking south on Victoria Park from Eglinton to St. Clair today. Obviously, I crossed the North York/East York boundary (and of course, Scarborough is on the other side of VP). One of things I’ve always noticed on this stretch is as soon as you get south of Parma Court, side street intersections with VP become way more frequent (most of East York, along with Old Toronto and York, uses the grid street system even in neighbourhoods, where Etobicoke, North York, and Scarborough, that’s few and far in between). Also, most streets on the 3 inner boroughs have sidewalks on both sides, where in the 3 outer boroughs, that’s hit or miss (either just a sidewalk on one side or no sidewalk at all).

The big way the boundary here is noticeable is sidewalk design. There tends to be a grass median in between the road and sidewalk in the 3 outer boroughs, which isn’t as common in the 3 inner boroughs. Here, this photo is taken in North York, and you can see the median dying off before it hits the East York border (I believe that house on the right is in East York or at least on the border).

I’d say this isn’t just the North York/East York boundary, but the boundary of “Inner Toronto” and “Outer Toronto” which seems to respect the former municipal boundaries here, but not in all spots (I’d say southwest North York qualifies as “Inner Toronto”, as does extreme south Etobicoke and extreme southwest Scarborough).
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