More “Old” Streets of Toronto

In January, I looked at the origins of “Old” Streets of Toronto — that is, main Toronto roads that have the moniker “old” preceding their names. In many cases, these stories involved the re-routing of streets to create a more direct path for travellers. In doing so, the old paths were sometimes not eliminated.

Tremaine’s Map showing old courses of Toronto’s streets.
Source: Old Toronto Maps
Created by: Bob Georgiou

Here are six (and a half) more “Old” Streets of Toronto and their quick histories:

Old Dundas Street

Year rerouted: ~1929

Historically, the main crossing over the Humber River on Dundas Street was located about two hundred metres south of the current bridge. This section of Dundas made up the old community of Lambton Mills and served as a main entrance into Toronto from the west on the Dundas highway. There were several versions of Dundas Street bridges here over the years — some made of wood, some iron, but all narrow for traffic and susceptible to the flooding waters of the Humber.

1924 Goads Fire Insurance Map of old course of Dundas Street.
Source: Goad’s Toronto

In 1929, a new high-level bridge was completed over the Humber. This altered the main course of Dundas Street to the north. The old course became “Old Dundas Street”. For nearly thirty years, the two Dundas Street bridges existed alongside each other. In 1954, the devastating effects of Hurricane Hazel left the Old Dundas Street bridge in a dilapidated state; it was finally demolished several years later. Today, Old Dundas Street exists on both sides of the Humber River mostly as a quiet residential street. Lambton House, a historic inn turned museum, is a leftover of Old Dundas Street and Lambton Mills’ prominence.

“A New High-Level Bridge”, The Globe, January 16, 1929.
Source: Globe and Mail Archives.
1950 Aerial Image of Dundas Street and Old Dundas Street.
Source: City of Toronto Archives
Old Dundas Street, 2021.
Source: Google Maps

Old Weston Road

Year rerouted: ~1948

Weston Road takes an interesting route through northwest Toronto, running diagonally through its street grid from the historic town of Weston (makes sense, eh?) and creating some unconventional intersections. North of St. Clair Avenue, the route of Weston Road was historically located east of the present road on the other side of the train tracks. It made up the historic village of Carlton with St. Clair and Weston as its nexus. It is highlighted by the still standing, yet altered Heydon House Hotel, built 1890. Weston then ran south to join with Dundas Street.

1851 JO Browne Map of Toronto showing Weston Road and the village of Carlton.
Source: Old Toronto Map
1927 Heydon House.
Source: City of Toronto Archives

Around the 1890s, another “branch” of the street was built north from Keele Street running parallel to the railway on its west side. This street took on the name “Weston Road South”. In the 1910s, the street was completed to join with the main Weston Road.

1908 Map of Toronto showing Weston Road.
Source: Old Toronto Maps
1909 Map of Toronto showing Weston Road.
Source: McMaster University
1910 Old Weston Road bridge over C.P.R.
Source: City of Toronto Archives

Perhaps because Weston Road South offered a more direct route south into the city, it formally became the more prominent road in the 1940s. First, an “Old Weston Road” began to refer to the section of Weston Road between the railway and Hillary Avenue. This meant that at one time a person could stand at the intersection of Weston Road, Old Weston Road, and Weston Road South. In 1948, Weston Road South became just Weston Road. Also, the entirety of the older eastern section of Weston Road was renamed Old Weston Road, save for the section between the tracks and Hillary which was added to Rogers Road. As the tracks to the south grew, the section of Old Weston near Dundas became severed from the rest of the road. Today, Old Weston Road is a mostly residential street.

1945 Map of Toronto showing Weston Road.
Source: Old Toronto Maps
1948 Toronto Transit Commission Map showing Weston Road.
Source: University of Toronto Map & Data Library.
1951 Map of Toronto showing Weston Road.
Source: University of Toronto Map & Data Library.

Old Eglinton Avenue

Year rerouted: ~1957

For an east-west street that has become so vital to Toronto’s street grid and home to many neighbourhoods, it is difficult to imagine that Eglinton Avenue did not always exist in one harmonious stretch of road. However, it took some doing to make it into the street of today. Until the 1950s in the eastern half of Toronto, Eglinton Avenue terminated near Brentcliffe Road in Leaside and did not resume again until Victoria Park Avenue in Scarborough. The area in between them was about a five-kilometre stretch of farmland and two ravines — that is, both the east and west branches of the Don River. In the mid-1950s, a massive project was undertaken to join the two sections.

1950 Aerial Image of the future location of the Eglinton Avenue East extension.
Source: City of Toronto Archives
1953 Map of Metropolitan Toronto.
Source: York University Archives
1954 Aerial Image of the future location of the Eglinton Avenue East extension.
Source: University of Toronto Map and Data Library

While an “Old Eglinton Avenue” seems to come out of the events of the 1950s, it seems a little unclear why. The street runs parallel to the “new” road for about half a kilometre west from Bermondsey Road. Like the surrounding area, it mostly houses industrial buildings. As Eglinton did not seem to exist between Leaside and Scarborough (at least not in any formal sense), the story of Old Eglinton is a bit of a mystery. Hiking The GTA has located an old roadbed for an “Old Eglinton Road“. This may have been a farm road or a line that divided farm lots. It is also notable how Old Eglinton Avenue aligns with a “pencilled in” Eglinton Avenue between Victoria Park and Leaside, so a theory may lay in that idea.

Extension of Eglinton Avenue east across the West Don River, 1955.
Source: City of Toronto Archives
Old Eglinton Avenue, 2020.
Source: Google Maps

Old York Mills Road

Year rerouted: ~1972

The valley near Hogg’s Hollow has proven to be an obstacle to road transportation several times in its history. As I previously noted, Yonge Street was realigned in 1835 after skirting east to better tackle the West Don ravine’s topography. Because of this same geography, Wilson Avenue terminated at Mason Boulevard, meaning there was no direct east-west crossing at Yonge Street as we know it today. In 1972, a project was undertaken to extend Wilson to meet with Yonge and York Mills Road.

1971 Aerial Image of York Mills Road and Wilson Avenue.
Source: City of Toronto Archives
“Extension of Wilson Avenue”, Toronto Star, May 28, 1972.
Source: Toronto Star Archives

To make this extension happen, a curved road was constructed from Wilson Avenue which then crossed Yonge Street and joined York Mills Road between Campbell Crescent and York Ridge Road. This meant the straight section of York Mills near Yonge Street was effectively separated from the main route, becoming “Old York Mills Road”. Today, Old York Mills houses a trailhead, a passenger pickup zone for York Mills Station, a condominium, and a church.

Old York Mills Road and Wilson Avenue Extension, 1973.
Source: City of Toronto Archives.

Old Kennedy Road

Year rerouted: ~1987

Kennedy Road just north of Toronto is a prime example of how of a noticeable curve in a street sometimes denotes a street was re-engineered. Kennedy existed in two separate sections north and south of Steeles Avenue, the Scarborough-Markham town line. The roads were about six hundred metres apart, meaning a northbound traveller from Scarborough had to jog east and then north again to continue into Markham. The area as a whole is and was known as Milliken, a historic community with the uncommon characteristic of existing within both municipalities.

1954 Aerial Image of Kennedy Road.
Source: University of Toronto Map & Data Library

In 1987, the two sections of Kennedy Road were connected by a curving road running north from Steeles which veered east to meet the Markham section of Kennedy just north of the newly created Denison Street. The circumstances behind the re-alignment were unclear, but given Kennedy Road’s history as a ‘highway’ in Scarborough and the tendency in and around Toronto to harmonize streets within bordering jurisdictions, it is easily conceived why the jog was removed.

1987 Aerial Image of Kennedy Road.
Source: City of Toronto Archives.

The eastern section of Kennedy became “orphaned” and was renamed Old Kennedy. Old Kennedy stops at Denison and continues on as Fresno Court, which in turn ends at a cul de sac. A fence separates it and Kennedy Road. Old Kennedy Road is an interesting mix of industrial and residential, with several older-looking houses near Steeles, perhaps lending back to the days when it was a hub in the village of Milliken.

Fresno Court, 2020.
Source: Google Maps

Old Finch Avenue

Year rerouted: ~1993

Finch Avenue in Scarborough is relatively straight for much of its course from the North York town line to the Pickering town line — except in its most eastern part. Where Finch passed through Staines Road, the street at one time did a triangular job around the CPR tracks (the detour seems to have been created in the 20th century).

1916 Map of Townships, York, Scarboro, and Etobicoke.
Source: University of Toronto Map & Data Library
1954 Aerial Map Showing Finch Avenue.
Source: Source: University of Toronto Map & Data Library

Further along, Finch did another jog up Sewell’s Road before meandering across the Rouge River and around its valley. It continued straight toward Kirkham’s Road (today’s Meadowvale Road). As there is today, there was an uncleared section of land across to Beare Road, thus one would have to jog up again to Plug Hat Road and back down to reach Finch again. The street resumed once more on its way to the Pickering Border. This stretch of Finch between Sewells and Kirkham’s made up the historic community of Hillside which had a church, school, and mill. The village made up much of the Rouge lands today from Sheppard Avenue/Twyn Rivers to Steeles Avenue.

1965 Aerial Image of Finch Avenue.
Source: City of Toronto Archives.
1969 City of Toronto Directory showing Finch Avenue.
Source: Toronto Public Library

By the 1980s, changes came to Finch Avenue. Morningside Avenue curved from the south to meet Finch. Then, in or around 1993, the street was extended further north of Finch. This changed the alignment of the Finch/Staines intersection and effectively split Finch Avenue. Travellers moving east on Finch had to now follow the curving street north to Morningside Avenue and then curve back south via the same street. The east-west street on the other side was “Old Finch Avenue”, following the older, winding alignment. Because of this, the street bunks the trend of “old” streets which were leftover sections of the re-routed street; there is/was not ever a “newer” Finch Avenue that existed alongside the street. Old Finch terminates at Meadowvale Avenue; after Beare Road, it becomes Finch again and continues into Pickering for another eight kilometres.

“New Metropolitan Toronto Zoo Site”, Toronto Star, June 17, 1972.
Source: Toronto Star Archives
“Star Trek Run” Toronto Star, June 3, 1978.
Source: Toronto Star Archives
1983 Aerial Image of Finch Avenue.
Source: City of Toronto Archives

Today, Old Finch is mostly known for its ‘haunted’ Bailey bridge and being the northern border of the Toronto Zoo, whose postal address is 361A Old Finch Avenue. The reconfiguration at Staines also facilitated the Morningside Heights neighbourhood.

“Grand Opening”, Globe and Mail, May 20, 1993.
Source: City of Toronto Archives
2022 Finch Avenue.
Source: Google Maps

The Older Finch Avenue

Year rerouted: 1977

Old Finch Avenue in the Rouge Valley was not the first Old Finch in the city. There was once a severed section of the street near Victoria Park in the old community of L’Amoreaux when the street was realigned directly across the Scarborough-North York border. This curved realignment eliminated a jog along the town line for east-west travellers. This Old Finch Avenue was closed in 1977; Pawnee Avenue roughly follows its old right of way.

1975 Aerial Image of Victoria Park and Finch Avenue
Source: City of Toronto Archives
“Borough of North York Notice of Road Closing”, The Globe and Mail, September 9, 1977.
Source: The Globe and Mail Archives

For a Google map of “Old” Toronto Streets, click here.

Map of “Old” Toronto Streets.
Source: Google Maps
Created by: Bob Georgiou

If you have any information to add or have any stories from any of these locations, leave a comment below or email!

What’s In A Street Name?

A city’s streets can tell a lot about that city and its residents: who we are, where we came from, and who and what we value. In other words, names are a huge part of understanding our heritage. At least, that’s what I’ve discovered when looking at Toronto’s roads.

In general, Toronto streets fall into one of three  themes: (1) throwbacks to our British roots; (2) our city and community builders, and (3) literal descriptions (usually of the surrounding environment). If we really wanted to, we could also include a fourth category of streets that do not really have a rhyme or reason that we can tell, or their story has simply been lost.

First, some streets don their names after British royalty. Victoria Street and Queen Street are after Queen Victoria. The ‘King’ in King Street is King George (who might potentially also lend his name to George Street). Prince Frederick, Duke of York and Albany is honoured by, you guessed, Frederick and York Streets. These streets are the historical bigwigs across the pond.


In the second case, we have places like John and Simcoe Streets named after the city’s founder John Graves Simcoe, Cummer Avenue after Joseph Kummer of Willowdale, Leslie Street after arborist George Leslie of Leslieville, Bloor Street after brewer Joseph Bloore of Yorkville (and a seriously scary looking fellow), Denison Avenue after the George Denison the original owner of the land now known as Kensington Market (many other streets in area are named after his family as well), and Jarvis Street after the Jarvis family. Austin Terrace is named after the Austin Family who built and resided in the manor known today as Spadina House and Gardens Museum. At even a more local level, in early maps of Leslieville, we find streets that have now been redubbed, like Morley Avenue (now Woodfield), after men who were active in the community’s clay industry.


We don’t need to look any further than Old Toronto to see the last category play out. We find streets like The Esplanade. Sometimes near water, the esplanade (basically meaning road or waterway) nickname makes sense because at the time of its founding, the waterfront wasn’t as far out. Speaking of, Front Street was originally named because it followed the original coastline of Lake Ontario. Church Street one time housed many churches (leading to the Toronto ‘the Good’ moniker for the city) and at the foot of Parliament Street was Ontario’s first government buildings. River Street alludes to the adjacent Don River. Don Mills Road, which was once what we know today as Broadview Avenue (titled for the ‘broad view’ one sees of the city when passing over Riverdale Park East), refers to the early industrial mills situated on the Don River. Lot Street, a street we know today as Queen, referred to the parcels or ‘lots’ of land that ran to Bloor Street. Finally, Spruce, Elm, Oak are the names of roadways in the downtown area alone – presumably titled after the trees that lined them.

So what does this all say about us?

Our ancestors loved to pay tribute to the regime that founded the city as well as the Canadians that started the communities within the city’s confines…and that sometimes an unoriginal descriptor is perhaps the best name. This is all rightfully so. We should pay homage to our community founders and as much I support dumping the monarchy, they were instrumental in our history. And yes, it is fun and easy to be literalist.

What’s missing?

In Athens, I stayed on a street called 28 October Avenue – a date in which the Greek government said OXI in refusal to the Mussolini Fascists in 1940. Other cities employ the dates of revolutions from dictatorial or colonial rule (in the case of Latin countries, both). In other words, dates that resonate in the national and local consciousness of people. Do we have that in Canada and Toronto?

The 1st of July would be the most obvious choice. If anything most Canadians identify most with at least that day. I’d throw out a couple of other possibilities of a more local affiliation: 6 March Avenue and 27 April Street. The former reflects the day in 1834 when the Town of York was incorporated as the City of Toronto while the latter is in reference to the Battle of York in 1813 which marks the little known (and only) occasion when The Town of York was occupied by opposing American military forces.

Would these work in Toronto? Likely not. Although I sense that there is a growing connection between the population and its history, I somehow doubt most people could list off Toronto’s birthday or that a battle once took place on its land. Plus, not to discount their places in this city’s story, they do not have the “draw” that a revolution does. But it would be interesting to have anyways.

The other notable omissions are cultural icons within our streets. I can think of three: Mike Myers Drive in the Kennedy and Lawrence area, named after the famed Scarborough-born actor and comedian; Ed Mirvish Way, located beside the Royal Alexandra Theatre, is an homage to the great performing arts promoter; and the Martin Goodman Trail after the Toronto Star Editor-in-Chief. While the last of these is not a motor vehicle way, it is still a method people get around in the city and thus I have included it. I’d like to see more though. How about a Michael Snow Way? A Neil Young Boulevard? An E.J. Lennox Street? All three have made grand contributions to Toronto’s visual arts scene, music scene, and streetscapes respectively.

Lastly, I wonder about homages to the Aboriginal presence in the Toronto area. Yonge Street and Davenport Road were both originally Native trails, although their names do little to alert of that (although there is plenty of work done that tell those stories). Spadina comes from ishpadinaa meaning “be a high hill or sudden rise in the land” in Ojibwe.  The High Park neighbourhood features several ‘Aboriginal’ and non-PC-named streets including Indian Trail, Indian Road Crescent, and Indian Road. The latter intersects with Algonquin Avenue, one of the Native groups of Ontario. In the Weston Road and Rogers Road area one can find Seneca and Cayuga Avenues. These are of course two tribes of the Iroquois Confederacy. The Iroquois connections continue with Hiawatha Road in Leslieville, as Hiawatha is the legendary leader who united the groups.

SenecaCayuga    AlgonquinIndianRoad

I quite honestly expected a lot less representation than I discovered. This is of course only a start, however. Aside from Spadina, which is actually situated on a hill near Casa Loma, their situations within the city are questionable. Do the ‘Indian’ streets follow a historical Aboriginal trial? Cayuga, Seneca, and Hiawatha are all in historical working class, industrial areas, ironically near brick yards. I wonder if there were any reason for the selection of those names in those areas.

How do we name streets anyways?

Not surprising, the way we get our streets names goes through Toronto City Council. According to the City’s Honourific and Street Naming Policy, names should reflect the culture and heritage of the community they are located, have the support of that community, be positive, and not be made into any inappropriate nicknames or abbreviation. In terms of content, the document outlines more guidelines:


Streets should generally be named after people, places, events and things relatedto the City and citizens of Toronto. Proposed names should meet one of the following criteria:

1. to honour and commemorate noteworthy persons associated with the City of  Toronto;

2. to commemorate local history, places, events or culture;

3. to strengthen neighbourhood identity; or

4. to recognize native wildlife, flora, fauna or natural features related to the community and the City of Toronto.

In other words, these are the same categories I have identified through my own observations while examining maps of the city. A proposal can be put forth by a councillor or members of the community at large. These proposals eventually reach a Community Council (consisting of the four former municipalities of Metro Toronto; Toronto and East York consisting of one). They might also reach City Council at large for a final say.

There are several things to note in terms of the points I raised already. First, the policy goes on to say in redubbed streets, names of living persons should be avoided. This makes my Neil Young suggestion perhaps a bit difficult, even though a commemoration of Mike Myers seemed to get through. Second, there is no explicit mention of the use of dates, but looking at section 6.1.2 (b), the argument could be made. Again, I do not think there will ever be a 6 March Boulevard. The connection to the city’s heritage does not seem to exist in that form.