Monday, October 19, 2009

Retrospectives: Sheppard, Leslie, and the Don

One of the most tortured intersections I’m aware of in the city is that of Sheppard Avenue and Leslie Street. Leslie is, to this day, a slew of discontinuous streets they never really took the trouble to unite; there are at least four sections of it that I know of. But since the 1950s, the intersection of Sheppard and Leslie has been torn up, rerouted, connected and disconnected in myriad ways for more reasons than you can shake a stick at. The 401’s been built through, two level crossings have been underpassed, the 401’s been widened, both streets have been widened, the dogleg caused by Don River’s been corrected by means of a much larger bridge they now share, a subway line’s been channeled under Sheppard Avenue... all this in just 50 years.

One day, I mean to seriously blog about just what’s happened to these two streets in the vicinity of their intersection (or, till about 1968, intersections-plural). Just for now, though, I’d like to share a delightful discovery from the City Archives: a shot of the Sheppard Avenue East bridge over the East Don River from 1964. (The shot faces east, as do the others.)

This photo was taken right on the verge of suburbia overwriting the hills and dales of the area. Just for the moment, it was a pleasant country road. See the bridge there, just a simple two lane affair carrying Sheppard alone over the Don. Beyond it, you can see Leslie Street heading away to the north. Back then, there was no Leslie Street on the south side at this point: it would have had to cross the Don. The southern part of Leslie was way up the hill behind the photographer. Anyone traveling along Leslie and wishing to continue along it had to use this stretch of Sheppard for many, many years to do so.

Here’s how the intersection looks now, seen from nearly exactly the same location in 2009. Leslie now crosses Sheppard here, not just meets it; Leslie no longer bows to Sheppard at a stop sign while Sheppard traffic plows through without a thought. They both cross over a much larger bridge that dwarfs Sheppard’s span in 1964.

Taken earlier this decade, here’s another view of the intersection, looking in the same direction. This shot was taken from the bridge that now overpasses Sheppard at the site where Leslie Street once T-junctioned with it on the west side; this is now called Old Leslie Street, a short stub that serves a few businesses. Oddly, thanks to the bridge, it now crosses Sheppard here, which it did not do when it was a going concern up to the 60s. But you can see the “new” run of Leslie south of Sheppard there on the extreme right. Also visible is Leslie Station, a stop on the Sheppard subway line that opened only four or five years ago. The stretch of Sheppard in the foreground was what once united these two legs of Leslie Street, though you would have seen a slope down from here before 1968 when the bridges were put in. Directly behind me in this shot is another bridge for what was a level crossing (more on this in another post soon).

Just for good measure, a couple of aerial shots to show some of the changes. The first shows the area in 1956. The big mess in the middle is Hwy 401 under construction. Leslie runs up and down in this view (as it runs north-south). Leslie’s course has already changed in this view; it used to go straight north till it reached that line of trees in its course and then shot westerly, the course of which you can still see in this shot. Running across the top is Sheppard Avenue, where you can see the wide spread between the two runs of Leslie Street.

And this is the view from 1967. You can see Sheppard Avenue has been temporarily detoured at the Don so that the new bridge it will share with Leslie can be put in. Most dramatically, you can see the pencil-work of planners emphatically planning Leslie’s newer, truer course north to Sheppard. Near the middle of the shot is North York General Hospital, newly built. Subdivision construction is evident at the bottom right, but not yet at the upper right. It was literally only months away.

It would certainly be illustrative to compare those views with this one.


  1. I remember the Bailey bridge over the Don from the 1967 aerial shot when the intersection was being straightened. On Old Leslie south of Sheppard – the hamlet of Oriole – there was a church and school. I could be mistaken – but I thought they were still there after Leslie was realigned – but were eliminated when the railway overpass and 1200/1210 Sheppard were constructed.

    There is another fine shot of Leslie St south of the 401 and the railway tracks on the Toronto Archives website – and if you want to see how the intersection looked in the 1870’s you should check out the online Canada County Digital atlas. There was another road running east of Leslie to Woodbine south of the first lot south of Sheppard– near where Leslie veered off to the west, giving access to a sawmill at the south end of a pond in the Don River.

    The estate on the north east corner of Leslie & Sheppard was called Wynyates. It was built by W. Eric Phillips – who was one of the partners of Bud McDougald (who lived up the street at Finch) in the Argus Corp – and it is still there. The access to the house was a driveway built into the side of the hill – with a caretakers house at the top. You can clearly see the driveway and both houses in the 1956 picture.

  2. Hi, Anna, wow, what I wouldn't give to have been able to have seen the Bailey bridge back then... or at least a photo of it.

    I'm not sure myself when the places at then end of Leslie were torn down... all I know for sure is, they're well and truly gone. There's a whole lot of empty nothing there now. Hard to look at how lovely it once was and see how stark it is now by comparison. I do know that the bridge that carries the railroad tracks dates from 1968 (it's impressed into the concrete supports); presumably, the bridge that now carries Old Leslie over Sheppard is contemporaneous to that.

    I think I know the shot of the Leslie Street level crossing you're speaking of... I used it as a reference to try to recreate the shot. Not easy... so much has changed there. I'll have to blog the results.

    I never knew about Wynyates. I have a vague sense of a road that once ran though the land south of Sheppard; there used to be a bridge across the Don just north of the Duncan Mill Road bridge, with an attendant pumping station or something. There are a couple of ruined buildings there. I gather they had something to do with Graydon Hall across what's now Don Mills Road from there, but I don't know much about that either.

  3. One of the benefits of advanced age... I will try and find a picture of the Bailey Bridge (very exciting for a little kid).

    There are pictures of Oriole Public School and Oriole Methodist/United Church from 1956 on the TPL - Historicity website.

    Keep up the good work.

  4. p.s. The pictures were taken by James Salmon. I should have read your most recent posts first.

  5. Hi again, Anna, it's great to see you back. :)

    It would be just incredible if you actually are able to find a shot of that bridge -- it probably ought to be the city archives, too. It's hard for me to even imagine it. Times I've been by the river there, I just don't see any evidence of it. Only the aerial shots can convince me, but they sure did a great job afterwards erasing the disruption it caused!

    I've neglected to post my level crossing shots... I should really do that this evening. :)

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