City
What expressways used to look like in Toronto
As much as Toronto's expressway system may help to define the city as it exists today, prior to the 1950s not a single controlled access highway could be found running through the city. While the QEW dates back to the early 1930s, it wasn't until widening efforts 20 years later that it would become a true freeway. The same can be said for Highway 2A, a major section of which became the stretch of the 401 that extends east from Scarborough to Oshawa in 1952. Also dating back to the 1950s is the 400, which was then referred to as the Toronto-Barrie Highway.
The 1960s would witness expansion of the expressway system in Toronto, but not to the degree that provincial and city officials planned at the time. The DVP opened in 1960, but a number of other major highways proposed during this period were ultimately killed before completion: the notorious Spadina Expressway (the built section of which is Allen Road), the highway 400 extension to the Gardiner (built to Jane Street) and the Crosstown highway. Of these, the story of the ill-fated Spadina Expressway is surely the best-known. I won't repeat it here, but it's worth taking a look at the last photo in this lost to get a sense for what kind of impact it would have had on the areas in its planned path.
Since the 1960s, new highways have appeared around Toronto — e.g. the 427 (an expansion of highway 27), the 410, and the 407 — but none, of course, that run directly through the urban core. I suspect we've passed the time in which proposals to run freeways through downtown neighbourhoods will be seriously tabled, but one never really knows.
For more detailed information about Toronto expressways and their history, an excellent but manageable source is The Expressways of Toronto (Built and Unbuilt) on Transit Toronto.
PHOTOS
400
400 at 401 in 1952 (via the Ontario Ministry of Transportation)
400 at 401 in 1969 (via the Ontario Ministry of Transportation)
401
401 and Yonge in 1958
401 at McCowan in 1961
401 and Highway 27 in 1961
401 and Allen Road in the 1960s (via Ontario Ministry of Transportation)
401 east of Allen Road in 1967
401 in the 1980s looking toward the 400 from Islington overpass
DVP

DVP near Eglinton Actually an expressway-looking Eglinton Ave East (see comment from Rick McGinnis below)
DVP under construction late 1950s
Gardiner Expressway
Gardiner Expressway, aerial view over Jameson in the 1960s
The Gardiner at Dufferin looking east in 1959 (prior to opening)
Gardiner and CN Tower mid 1970s
QEW
Entrance to the QEW and monument 1940
QEW and Highway 27 in 1958
QEW and bus in the 1960s
QEW near Highway 10 in the 1960s
QEW in Oakville 1967
QEW in Port Credit 1967
W. R. Allen Road / Spadina Expressway
Building what was then expected to be the Spadina Expressway in 1963
Allen Road / Spadina Expressway to Eglinton. Look what was next on the horizon before plans to head further south were stopped (that's Cedervale Park just beyond the depression dug out for the highway)
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Photos from the Toronto Archives unless otherwise indicated


Discussion
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Huh?
It's the eastbound 401 where the 409 eastbound empties onto the 401.
I'd agree with Rob, picture looks like it was taken from the middle of the Islington bridge looking west over the 401.
http://tinyurl.com/6788p8d (Streetview of the same)
Thanks, updates made.
Thanks, updates made.
Drive a couple of blocks from where that photo was taken and you'll cross the DVP.
Oh, well. I'll leave the photo in with a note, but I have to ditch it as the lead.
(1)interesting to see Yorkminster Citadel already at Yonge + 401 in 1958 (and back when its side gable windows were wide open rather than blocked-in)
(2)the Gardiner/Jameson shot is probably more or less contemporary with (if not earlier than) the 1959 from-Dufferin shot
(3) the CN Tower shot would be 1974 (that's when it was at that stage of construction, right before the Skypod took form)
The City owns the S/E corner as well, where there's parking (leased out).
The City also has recently approved selling off the land, beginning with the N/E corner, (subject to a deal); but with the note that station for the Eglinton LRT must be accommodated under any new buildings.
*****
To the threat in general; may I, duly bemoan the expressways that were built, particularly in the form they were built; and petition for their removal where practical (particularly Allan Road and Black Creek Drive).
I say this, btw, for the quick judgers, as a car owner and driver; who just things the place for freeways is at the urban periphery and not through sensitive natural areas either.
A similar project could be the crown jewel for the Ford Administration. How many bike lanes does one need to rip out to pay for a new expressway?