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Transportfan

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The Middle Road was the precursor to the QEW between the-then Etobicoke and Burlington. Unlike the QEW though, it only ran as far east as the former Highway 27 (now 427) before being tying into the-then Queen Street, now The Queensway (yes it was that Queen St.), which of course led drivers into the city. Here's a 19th Century map of the road in Toronto Township (Mississauga):

map1.jpg



Here's a map of the Etobicoke side. You can see the present-day Dundas Street, Evans Avenue, and the Queensway, which had a jog in it at present-day Kipling Avenue (which was unusual as other roads jogged north with respect to their Old Toronto sections at the Humber, as is the case with Bloor Street). The northern jog was bypassed in the early 20th Century when the southern stretch was extended to hook into The Middle Rd. The northern jog became today's North Queen Street.

Map3.jpg



Toronto Township council wanted to bridge The Middle Road over the Etobicoke Creek, and built a bridge in 1909. However, the bridge was built south of The Middle Road and only connected to it via a farm Lane. The Etobicoke side was connected to Evans Ave. Here's a pic from 1956 showing the bridge leading to said farm lane on the Toronto Township side, and Evans Ave (here already long bypassed, and bisected, by the QEW, which was the actual extension of The Middle Road itself across the creek):

map2.jpg



Here is an aerial of the new QEW west of Hwy. 27 in 1940, showing the abandoned pavement of the old connector between The Middle Rd. and Queen St./Queensway on the left:

qew-103_lg.jpg



Google maps view of the present Sherway Drive (the Toronto section formerly being part of the road which is now Evans Ave), which used the original 1909 bridge:

map4.jpg


And the bridge itself, today used solely as a pedestrian and cyclist crossing:

1024px-Middle_Road_Bridge_IDM_3026.jpg


 
I'm wondering whether the Queensway *itself* from Kipling to Brown's Line/(4)27 predated the Middle Road extension--that is, the latter only really started at the arc on the left of the 1940 picture above (and it appears that said arc bypassed a straightaway).

Also, the ghost of that arc (by then downgraded to some kind of access road) remained apparent in aerial photos as late as the 1970s.
 
^^ The Queensway (then still Queen St.) existed at the same time as The Middle Road, but the bridge now carrying Sherway Dr. was built in 1909 and didn't actually connect to The Middle Rd. itself and was actually a bridging of Evans Avenue, not The Queensway. The section of The Queensway west of Kipling was built to replace the northern jog (bypassed as North Queen St.) as it led more directly to The Middle Rd. as the concession roads on each side the Etobicoke Creek didn't line up well.

The Queensway in Mississauga was built as an eastward extension of Upper Middle Rd. which originally ended west of Hurontario to connect to The Queensway in Toronto in the 1970s decades after the QEW (the former Middle Rd. in Mississauga) was disconnected from Queensway and extended east as a new highway.

Here's the Etobicoke side with present roads added for comparison (Solid black for the QEW; thick dashed black for the present Queensway; thin dashed for former roads or designations:

New map 2.jpg


EDIT: added map
 
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^^ The Queensway (then still Queen St.) existed at the same time as The Middle Road, but the bridge now carrying Sherway Dr. was built in 1909 and didn't actually connect to The Middle Rd. itself and was actually a bridging of Evans Avenue, not The Queensway. The section of The Queensway west of Kipling was built to replace the northern jog (bypassed as North Queen St.) as it led more directly to The Middle Rd. as the concession roads on each side the Etobicoke Creek didn't line up well.

The Queensway in Mississauga was built as an eastward extension of Upper Middle Rd. which originally ended west of Hurontario to connect to The Queensway in Toronto in the 1970s decades after the QEW (the former Middle Rd. in Mississauga) was disconnected from Queensway and extended east as a new highway.

Here's the Etobicoke side with present roads added for comparison (Solid black for the QEW; thick dashed black for the present Queensway; thin dashed for former roads or designations:



EDIT: added map
Actually, I was thinking of the present-day Queensway from Kipling up to (4)27 as having possibly predated the Middle Road connector (though post-dating the above settlement map)--there either are or have been houses along that stretch that seem pre-1930s. (W of QEW didn't arrive until the impending Sherway Gardens era in the late 1960s; the Mississauga connector came later still.)

Also, the QEW "bend" would be right at (4)27--the pre-QEW Queensway connector actually met the Queensway one concession to the E, around where the East Mall is now. (The "stub" of it is visible in the 1947 map here, at the bottom--and you can see how the Queensway "extension" ended cold at 27)
(And it's still evident in 1977)
 
Actually, I was thinking of the present-day Queensway from Kipling up to (4)27 as having possibly predated the Middle Road connector (though post-dating the above settlement map)--there either are or have been houses along that stretch that seem pre-1930s. (W of QEW didn't arrive until the impending Sherway Gardens era in the late 1960s; the Mississauga connector came later still.)
The Queensway extension/bypass possibly did predate the Middle Rd. connection but I can't find maps from the early 20th Century to confirm that, but it seems more likely it was specifically built to connect to The Middle Rd. An eventual separate route though Etobicoke for a divided highway might have been considered later in any case, and indeed was built as part the later QEW, meaning building houses on the extension/bypass wouldn't be an issue.

Also, the QEW "bend" would be right at (4)27--the pre-QEW Queensway connector actually met the Queensway one concession to the E, around where the East Mall is now. (The "stub" of it is visible in the 1947 map here, at the bottom--and you can see how the Queensway "extension" ended cold at 27)
(And it's still evident in 1977)

I was roughly illustrating the basic point, but the connection was slightly further east as you said--good eye for detail! The Queensway "extension" was actually a bypass that created North Queen St, which was too far north to make a good connection; notice the X's that are now parts of the old road that are just cul-de-sacs on both sides of the tracks.
 
I suspect that as per the map, the real reason for the Queen St "jog" is that the survey system was different W of Kipling--that is, the farm plots went N/S rather than E/W, and thus North Queen formed part of a sequence that included Horner and, I suppose, Burnhamthorpe and Rathburn (even though the latter ran to Islington) as well. So with that in mind, it's possible that Queen/Queensway was "punched through" earlier with further land subdivision, and it was less about a direct connection into Toronto Township than about a direct connection to the Brown's Line/27 corridor. And as far as said "subdivision" goes, it might be less about suburbanization than about, shall we say, rural/exurban "intensification": farm lots broken up into individual plots and market gardens and the like. Then in the 1930s, they would have built that "arc" and connected the possibly-already-extended Queensway into the Middle Road.

While North Queen bears the name "North Queen", it could just as well be that early traffic was more obligated to jog south to Evans as a kind a "South Queen" headed into Toronto Township.
 

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