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What Dufferin Street used to look like in Toronto

Posted by Derek Flack / December 2, 2013

Dufferin Street History TorontoDufferin Street might not conjure much positive nostalgia for riders of the 29 bus as it slowly plods its way to and fro on the pot hole-strewn road, but it is, of course, a stretch filled with rich history, from the presence of the CNE at its southerly tip to the Queen Street Subway to the long gone racetrack south of Bloor. Named after Govener General (1872-1878) Frederick Hamilton-Temple-Blackwood, 1st Marquess of Dufferin, the street was one of the original concessions running north from Lot Street (now Queen). Although mostly rural north of Bloor at the turn of the century, the area around Queen and Dufferin was already a hub of activity in the late 1890s.

So much so, in fact, that the city decided that the level railway crossing at Dufferin and Queen was no longer viable based on traffic delays and overall safety. The construction of the Queen Street Subway - often referred to as the Dufferin overpass - resulted in a 100+ year jog in which drivers and cyclists had to divert to Gladstone before returning to the street north or south of the rail bridge. While the overpass still remains, the jog was (thankfully) eliminated a few years ago.

Current construction on the street involves the replacement of the bridge near the entrance to the CNE grounds, a structure that dates back to 1911. Dufferin meanders as it reaches its southerly tip on account of the fair grounds, which hosted the Exhibition as early as 1879. Not much remains from this period, but the Ex is still going strong some 130+ years later.

If there's one bit of of the street's history that not too many people know about, it's the racetrack that once sat where Dufferin Mall does today. Opened in 1907, the track was a popular destination until its eventual demolition in 1955. Needless to say, it served as the prefect site for a mall as the land on the west side of the street was almost entirely undeveloped south of Kent Public School. Not everyone will consider the current occupant an improvement, but at least Dufferin Grove Park has been preserved for all these years.


201321-duf-south-queen-1898-ed2.jpgDufferin looking south of Queen, 1898

20131133-duf-north-queen-1898.jpgDufferin looking north to Queen, 1898

201321-dufferin-race-track-1910-ed2.jpgDufferin racetrack, 1910

201321-duf-sw-corner-1911-ed2.jpgSouthwest corner of St. Clair and Dufferin, 1911

201321-duf-north-dav-1912-ed2.jpgDufferin north of Davenport, 1912

201321-dufferin-grove-park-1913-ed2.jpgDufferin Grove, 1913

201321-dufferin-st-pier-012-ed2.jpgDufferin Pier, 1912

2013211-duf-st-clair-ne-DO.jpgNortheast corner Dufferin and St. Clair, 1920

201321-dav-west-duf-1923-ed2.jpgDavenport looking west from Dufferin, 1923

201321-duf-st-clair-streetcar-24-ed2.jpgStreetcar at Dufferin and St. Clair, 1924

201321-king-duf-1928-ed2.jpgKing and Dufferin, 1928

20131133-aerial-duf-track-1930.jpgAerial of Dufferin racetrack, 1930

201321-dufferin-nrth-college-1948-ed2.jpgDufferin north of College, 1948

201321-duf-college-1948-ed2.jpgIntersection of Dufferin and College, 1948

201321-duf-south-college-1949-ed2.jpgDufferin looking south of College, 1949

201321-duf-south-dundas-1951-ed2.jpgDufferin south of Dundas, 1951

201321-dufferin-eg-area-1950s-ed2.jpgDufferin and Eglinton, 1955

201321-duffern-bridge-arch-1959-ed2.jpgDufferin Bridge, 1959

201321-dufferin-401-better-1960-ed2.jpgDufferin and the 401, 1960

Photos from the Toronto Archives



Skye / December 2, 2013 at 10:22 am
Amazing how even then a neighbourhood could grow and change rapidly in just a decade. In 1911, there's still detached houses surrounded by fields, by 1921, St Clair and Dufferin is wall-to-wall storefronts.
Matt Y / December 2, 2013 at 11:09 am
I love how certain parts of Toronto are still recognizable 100+ years later. Unfortunately, things change and buildings deteriorate but I'm all for keeping the building's facade (although I am kinda' pissed that the theater I saw all 3 original Star Wars films at is now a Pottery Barn).
Jonathan / December 2, 2013 at 11:10 am
Great photos. Why has Dufferin road been allowed to deteriorate to such an extent? Why hasn't the road surface been kept up?
G / December 2, 2013 at 11:51 am
The sidewalks at Dufferin and College used to be much wider
iSkyscraper / December 2, 2013 at 11:54 am
People just don't realize how muddy and treeless Toronto used to be. Not all progress was bad.

That Dufferin/401 image is shockingly rural for 1960. Amazing.

I know it would be a ton of work, but pasting links to current-day streetviews of each photo would make for endless fun. Here is the modern match to that Dufferin and St. Clair 1920 shot -- all of the buildings are still there:
Torontonian replying to a comment from Jonathan / December 2, 2013 at 11:56 am
Dufferin Street is a major north-south axis and
is otherwise known as a side road.
The side roads are the complement to concession
roads. Bloor, St. Clair, Queen, Eglinton
are concession roads.
Bathurst, Dufferin, Keele and Jane are side roads.
Side roads and concession roads form grids of
1 1/4 square miles (1000 acres) and are used
to help plan subdividing land for planning
and zoning purposes.
Gravel / December 2, 2013 at 12:10 pm
Road looks smoother than they are today.
TG / December 2, 2013 at 01:14 pm
@Torontonian, you have it backward. Concessions are north south and side roads east west. The grids are 1 1/4 square miles and 800 acres which were then divided into 8 - 100acre farms per block.
Torontonian replying to a comment from TG / December 2, 2013 at 01:23 pm
I should have said 1 1/4 miles square
e.g. 1 9/16 square miles (1000 acres).

Historical maps show Bloor Street as the
first concession from the baseline
which was Queen Street.

There may be some places where the axes
of concession and side roads are as you say
they are but here in Toronto it is as
I stated.
mike / December 2, 2013 at 01:24 pm
biking on Dufferin is mountain biking, especially north of Eglinton - the road is three dimensional! totally rad.
TG replying to a comment from Torontonian / December 2, 2013 at 01:38 pm
@Torontonian interesting. Thanks
Tingy / December 2, 2013 at 04:37 pm
if RF had it his way you wouldnt be allowed to bike in toronto, the roads would only be for white suburbanites and their SUVs
Shirley / December 2, 2013 at 07:52 pm
Just wanted to say thank you to the residents of Ward 15 (Dufferin is big business around here). Your Christmas lights look beautiful.
Shirley / December 2, 2013 at 07:53 pm
Just wanted to say thank you to the residents of Ward 15 (Dufferin is big business around here). Your Christmas lights look beautiful.
Shirley / December 2, 2013 at 07:53 pm
Just wanted to say thank you to the residents of Ward 15 (Dufferin is big business around here). Your Christmas lights look beautiful.
Ash replying to a comment from iSkyscraper / December 2, 2013 at 09:32 pm
Visually, that Dufferin/401 shot is not all that different today - I walk across that entrance ramp frequently. Or run, as the case may be, as one of the onramps has no crosswalk or stoplight to this day.
Markus / December 2, 2013 at 11:34 pm
Ahh the Dufferin bridge so beautiful. I went to go to Midevil Times this weekend and didnt realize you can't even cross it anymore. It will be missed now that Rob Fords office is tearing it down.
John P / December 3, 2013 at 11:44 am
The bridge at the EX needs to be replaced ASAP. It's pure BS that it's just closed until they get to it. It's an annoying detour for drivers and residents who live here.

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