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The City of Toronto Archives "TTC - 100 Years of Moving Toronto" online exhibition is live, fyi. Worth a look, some good historic photos, fantastic detail in the writing. If they do ever open a TTC museum, you could copy and paste quite a lot of this!
Link here
Had a look at the 1921 and 1934 maps on the Route Maps page. Didn't know there were plans for multiple diagonal routes across the city/metro.
Some observations:
King Georges Drive, currently a small street around Keele/Eglinton; there was a section around Wilson and Bathurst (since gobbled up by the 401)
Hollaman Road, now a a stub around Glencairn/Bathurst, was to be a longer road.

Aside from that, York Mills and Wilson were called Twentieth Ave (ref. 1921 maps) and Ellesmere was... Wilson Ave (ref. 1934 map).
 
Had a look at the 1921 and 1934 maps on the Route Maps page. Didn't know there were plans for multiple diagonal routes across the city/metro.
Some observations:
King Georges Drive, currently a small street around Keele/Eglinton; there was a section around Wilson and Bathurst (since gobbled up by the 401)
Hollaman Road, now a a stub around Glencairn/Bathurst, was to be a longer road.

Aside from that, York Mills and Wilson were called Twentieth Ave (ref. 1921 maps) and Ellesmere was... Wilson Ave (ref. 1934 map).

Norseman St. in Etobicoke was (believe it or not) once a separate section of College St, as was Howard Park Ave.

It's funny how in York Region, many old road names and numbers were never changed, such as 16th Ave. never being designated "Carrville Rd. E", but 17th was changed to Major Mackenzie. Or Highway 7 not officially being divided at Yonge despite address numbers being so divided. Stranger still, the original section of Davis Dr. was not given an east designation after being extended west of Yonge after Hwy. 9 was downloaded to become Davis Dr. W. even though it crossed Yonge fully in Newmarket.

Metro Toronto had a designation system where streets that crossed Yonge had east-west designations even for the municipalities that didn't cross it. Metro wasn't a single city, but it did structure itself as such on many metrics.
 
Norseman St. in Etobicoke was (believe it or not) once a separate section of College St, as was Howard Park Ave.

Though the two streets would roughly line up if they were joined across High Park and the Humber River, I really don't see it. Etobicoke Township had a separate land survey and road layout from Toronto/York Township. Note how Bloor Street jogs at the Humber River, and how St. Clair doesn't cross, and how the part of Eglinton Avenue in Etobicoke was once called Richview Side Road and was joined to Eglinton Avenue in the 1950s.

If you have any evidence that shows a proposed connection, I'd love to see it.
 
Though the two streets would roughly line up if they were joined across High Park and the Humber River, I really don't see it. Etobicoke Township had a separate land survey and road layout from Toronto/York Township. Note how Bloor Street jogs at the Humber River, and how St. Clair doesn't cross, and how the part of Eglinton Avenue in Etobicoke was once called Richview Side Road and was joined to Eglinton Avenue in the 1950s.

The surveys were different, but the concessions did approximately line up across the Humber. Eglinton in Etobicoke was once Richview Side Road, but it was the rough match of Eglinton. Rathburn was the never-connected equivalent of St.Clair.

Now Peel really did have an incompatible survey, with the concessions staggered midpoint from each other across the Etobicoke Creek or Hwy. 50. That's why there's poor connectivity with Toronto's streets, such as Burnhamthorpe, which runs between the "typical" grid roads and oddly ends after a relatively short distance in Toronto. The streets that do connect and run across much of both cities are either non-concession (on both sides) colonization roads like Dundas or Lakeshore, or modern extensions like Bloor or Queensway. That's also the reason Major Mackenzie doesn't continue into Brampton, and Hwy. 7 left a long bypassed section (today called Ebenezer Rd.) as it was later linked at Hwy. 50.

Eglinton is an anomaly as its a concession across both cities, but even that's a result of the boundary leaving the Etobicoke Creek to follow it, allowing the former Lower Base Line to continue until it hit Richview Side Rd.

But there was one case where the grid did line up: At Steeles.

If you have any evidence that shows a proposed connection, I'd love to see it.
I never said there was ever a proposed connection, but Norseman was called College, the same way The Queensway was once a broken section of Queen St that was called Queen.
 
The surveys were different, but the concessions did approximately line up across the Humber. Eglinton in Etobicoke was once Richview Side Road, but it was the rough match of Eglinton. Rathburn was the never-connected equivalent of St.Clair.
I've actually wished that these two could be connected. There really are too many bottlenecks in the street grid in Etobicoke.
 
Last year I posted some detailed maps of my concepts for highway networks in Windsor, London, and Chatham/Sarnia regions. I've been putting in a bit of work on refining these projects since then and have created some new maps with additional potential highways in the regions, as well as some other regions in Southwestern Ontario. Most follow existing or previously proposed/studied corridors. All municipal expressways have been re-designated under arbitrary provincial highway numbers in these maps, just for fun. I have also included regional population statistics, growth rates, and future population projections for 2051 using 2021 census data.

Windsor-Essex Region - Windsor's population can be expected to grow by around 50% in the next 30 years. While as much of the growth should be as concentrated as possible into Windsor proper, the adjacent suburban communities (Tecumseh, Lakeshore, LaSalle, Amherstburg) are growing faster due to Windsor's infrastructural limitations in the older parts of the city that prevent it from significantly densifying. As such, there will be some sprawl in the area as the region starts to re-emerge as a major industrial centre, in addition to significant expansions in greenhouse agriculture in Kingsville and Leamington. As such, I have proposed two new highways and one extension. HWY 422 (E.C. ROW) has been extended to the edge of Belle River and loops south to meet the 401. This avoids E-W redundancies that would be created with a Belle River bypass, and would support future industrial and residential growth in the area. HWY 423 (HWY 3) would be a 4-lane divided freeway from Leamington to Windsor. This would mainly serve industrial greenhouse traffic. It would emerge as a gradual upgrade of the existing/UC twinned Highway 3 as greenhouse industry expands. HWY429 (Parallels CR 9 and CR 20) would be a commuter link servicing Amherstburg and LaSalle that would first start out as a twinned, undivided highway and gradually be upgraded over time. CR 20, the current road that services the area, cannot easily be upgraded if demand swells, so a parallel route would need to be constructed.

Windsor Highway Network 2051.png


Lambton-Kent Region -
Growth remains sparse in Lambton and Kent, estimated to welcome only around 25,000 more people in the next 30 years. However, petrochemical industry will likely continue to expand on the Sarnia side of the corridor, and greenhouse agricultural industry will continue to grow around Chatham. This corridor, while crossing through a low-density and low-population demand area in the middle, does see a fair amount of traffic on the ends, with HWY 40 from Chatham to Wallaceburg and from St. Clair Township to Sarnia being incredibly busy (as someone who has driven the corridor at least 10 times at this point). HWY 414 (HWY 40) is another piecemeal project that would likely start with twinning (and later grade separation) in the section bypassing Sarnia, through to the northern parts of St. Clair Township. As for the south end, the priority would be twinning HWY 40 to Wallaceburg since there are a surprisingly large amount of commuters using that route, as well as bypassing Chatham to the 401. I had previously placed the bypass on the east side, but I have moved it to the west side so it would be attractive for people travelling from Windsor to Sarnia that don't want to cross through Michigan.

Lambton-Kent Highway Network 2051.png


London Region -
London has emerged as one of Canada's fastest growing regions. Based on the current growth rate, the London CMA has potential to reach almost 1 Million people in the next 30 years, just under doubling in size. While most growth will go to London proper, growth in peripheral communities like St. Thomas, Strathroy, Ingersoll, and Lucan can be expected to be significant. I believe that there is even a case to be made that we will start to see St. Thomas and London grow into each other in the near future, with the start of development of a new major commercial/industrial hub in Talbotville bridging the gap between the two. The main focal point of this concept is HWY 430, a major ring road link that follows the existing VMP in London and HWY 3 Expressway in St. Thomas. Priorities would be grade-separating the entire current VMP, creating a twinned at-grade road north of the city in Middlesex County that can be grade-separated when necessary, and creating another twinned, at-grade road that connects the St. Thomas Expressway to the 401 and the 402 which could be upgraded into a freeway when necessary. The section that runs along the southeast portion of the ring would be the lowest priority. The second link in the area is HWY 408, which I have envisioned as a massive, lengthy connector that runs all the way from London to Stratford, Kitchener, Guelph, Hamilton, and eventually Fort Erie. In London, it would run straight north until intersecting with HWY 7, and run a similar route through the area, south of St. Mary's and Stratford. More on that in the following images.

London Highway Network 2051.png


Grand River Region -
The Grand River area would be the priority focus of a Southwestern Ontario highway plan. The area, consisting of KWC, Guelph, Brantford, and Stratford, could be home to almost 1.6 Million people in the next 30 years, up from just over 900,000 currently, with KWC and Guelph carrying most of the growth burden. The most important fixture of this region under my concept would be HWY 408. As previously mentioned, HWY 7 would be upgraded running south of St. Mary's and Stratford, meeting up with HWY 8 in Kitchener. This entire section would carry the 408 number through to the new Kitchener-Guelph HWY 7, which along with HWY 6 through Guelph, would be renumbered as a continuation of the 408. The designation would carry through south past the Morriston Bypass along a new HWY 6 alignment. More on this corridor in the final image. HWY 425 (HWY 8/7/85) would be the northwest- running counterpart, being the Cambridge-Kitchener section of HWY 8 and the Waterloo section of HWY 8/85. This would be extended to Elmira. Finally, HWY 424 (HWY 24) would be the link between Brantford and Cambridge. The highway would circle around the northwest section of Brantford and then eventually parallel HWY 24 until Cambridge, where it would bypass to the East and meet up with the 401. I opted to go east instead of west because west of Cambridge is all quarries, which likely wouldn't result in good level of highway usage.

Grand River HighwayNetwork 2051.png


Hamilton-Niagara Region -
In the final section of my Southwestern Ontario highways concept, the Hamilton-Niagara region is also going to see significant population in the next 30 years, possibly as high as 1.7 million people, up an additional 500,000 or so. This area would hold the final section of HWY 408, which would run on the current HWY 6 corridor north of Burlington, down HWY 403, and then split off again on HWY 6 (which will soon be twinned), just south of the Hamilton Airport, and run all the way down to Port Colborne and Fort Erie. This corridor would provide bypass opportunities for traffic coming in from Fort Erie and take the heat off of the QEW, which should not be expanded any further due to sensitive fruit lands in the area, the same reason why the original 408 Mid-Peninsula Highway corridor was planned back in the 1990s/early 2000s. Said fruit lands have grown even more important to our maturing wine industry, which makes a bypass all the more viable. This also includes an extension of HWY 406 to Port Colborne to complete the network. I have also re-designated the Red Hill Valley/Lincoln M. Alexander Parkways as HWY 432.

Hamilton-Niagara Highway Network 2051.png
 

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