“Old” Streets of Toronto

Across the map of Toronto, there are several “Old” versions of major streets: Old Yonge Street, Old Leslie Street, et cetera. These are smaller and certainly older streets that predate yet still exist alongside their longer, newer counterparts.

How old are these “old” streets anyways? Why were they built as they were in the first place? Why were they replaced?

Tremaine’s Map showing old courses of Toronto’s streets.
Source: Old Toronto Maps

Here are five examples of “Old” Toronto Streets and their histories:

1. Old Yonge Street

Year rerouted: 1835

When Yonge Street was laid out in the 1790s, it was not the continuous straight path we think of today. The sheer length of the street almost welcomed obstacles. At York Mills, the challenging topography around the West Don River caused it to divert east just south of York Mills Road. It curved north and back west to join the original course. In 1835, the street was realigned and straightened. It seems in the 1920s, Yonge Street was re-routed again slightly to the west to allow for better automobile navigation.

1851 JO Browne Map of the Township of York.
Source: Old Toronto Maps
1950 Aerial showing Old Yonge Street and “new” Yonge Street.
Source: City of Toronto Archives.
“Yonge Street, at York Mills, Again Takes Altered Course” The Globe, February 26, 1921.
Source: Globe & Mail Archives.

Today, the old, “orphaned” course remains as part of Mill Street and Old Yonge Street. Old Yonge’s narrow, curvy course in parts maintains a rural quality. While at one time Yonge and Old Yonge once connected at its north end, this connection is now a roundabout. Finally, because of its length in the province, there are other Old Yonge Streets in Thornhill and Aurora.

Old Yonge Street, 2021
Source: Google Maps
Yonge Street, 2021.
Source: Google Maps.
Source: Google Maps & Bob Georgiou

2. Old Sheppard Avenue

Year rerouted: ~1934

Sheppard Avenue once existed in two separate sections on either side of the Scarborough-North York border. A traveller wishing to travel east or west through the two streets had to jog about 300 metres on Victoria Park to reach the other section. In 1934, the two roads were joined through a curving road running from just past Woodbine Avenue to the lower street in Scarborough. The move was the idea of Ontario Premier George S. Henry whose estate stood where the new Sheppard Avenue connection ran.

1965 Aerial showing Old Sheppard Avenue and “new” Sheppard Avenue.
Source: City of Toronto Archives

Today, the orphaned North York section of the old road now exists as residential Old Sheppard, albeit with small parts removed around Highway 404.

Old Sheppard Avenue, 2021
Source: Google Maps
Sheppard Avenue, 2021.
Source: Google Maps
Source: Google Maps & Bob Georgiou

More reading: Scenes From O’Sullivan’s Corners & Muirhead’s Corners

3. Old Lawrence Avenue

Year rerouted: ~1961

Lawrence Avenue is and was one of many streets which was impact by Toronto’s ravines. West of Victoria Park Avenue, Lawrence once took an interesting route across the East Don River Valley. Like Sheppard Avenue, there were two sections of the street: the Scarborough section which exists today and a North York section. The North York section jogged up Victoria Park over the Canadian Pacific Railway, ran briefly next to the track, and continued west for 1.5 kilometres. From here, it took a rather curvy route south down the East Don Valley, crossed the Don River via a bridge, and curved back north and west before continuing towards Don Mills Road. Presumably, this was easiest way in the 19th century to navigate the valley.

1860 Tremaine’s Map showing Old Lawrence Avenue
Source: Old Toronto Maps
Looking southwest at intersection of Victoria Park Avenue and Old Lawrence Avenue exit, 1958.
Source: Toronto Public Library
1959 Aerial showing Old Lawrence Avenue
Source: City of Toronto Archives
Lawrence Avenue E., bridge over East Don River, looking northwest,1955.
Source: Toronto Public Library

In 1961, Lawrence Avenue was straightened with a road directly connecting Victoria Park and Woodcliff Place, curling northwest from Scarborough with several new bridges to accommodate the Don River and CPR.

1960 Aerial showing Old Lawrence Avenue and “new” Lawrence Avenue under construction.
Source: City of Toronto Archives.
Lawrence Avenue East and CPR bridge under construction, circa 1960.
Source: City of Toronto Archives.

Today, the orphaned old road exists as roughly as part of Roanoke Road and, more famously, a short access road to the East Don Trail named Old Lawrence. The remaining section west of the river along with the old bridge itself have been lost.

Old Lawrence Avenue, 2021
Source: Google Maps
Lawrence Avenue, 2021
Source: Google Maps
Source: Google Maps & Bob Georgiou

More reading: Scenes From East Don Trail

4. Old Leslie Street

Year rerouted: ~1968

Like Lawrence Avenue, Leslie Street’s course at one time also had to divert around the East Don River. Also of 19th-century origin, a traveller going north on Leslie had to turn west for a short distance and then northwest for about 500 metres to meet with Sheppard Avenue. There was then a jog east on Sheppard, which included a bridge over the river and finally a left turn to travel north again.

1860 Tremaine’s Map showing Old Leslie Street.
Source: Old Toronto Maps
1953 Aerial showing course of Old Leslie Street.
Source: City of Toronto Archives
Sheppard Ave. East bridge near Leslie Street, 1964.
Source: City of Toronto Archives.

In the 1950s, with the construction of Highway 401, Leslie Street was altered to curve through the highway, but the course has otherwise remained the same. In 1968, the street was reconfigured again to join with Sheppard more directly. The Don River was also straightened and a new bridge was constructed which spanned the entirety of the new four-way intersection.

1967 Aerial of “new” Leslie Street under construction.
Source: City of Toronto Archives.

Today, the old course remains as Old Leslie Street, albeit a shorter version of the original route is available today to the public. It joins the new Leslie Street via Esther Shiner Drive. South of that street, there are City facilities. North of Esther Shiner, Old Leslie serves the Leslie Street TTC Station before it crosses over Sheppard via an overpass. It then curls back down to join the street (there is also a parking lot with an entrance to the East Don Parkland trail).

Old Leslie Street, 2021
Source: Google Maps
Leslie Street, 2020.
Source: Google Maps
Source: Google Maps & Bob Georgiou

More reading: Scenes From East Don Parkland

5. Cummer Avenue

Year rerouted: ~1969

The original course of Cummer Avenue west of Leslie Street was an 1819 construction. The street was laid out as a side road from Yonge Street by the Cummer family to access their holdings (a mill and camp) near the East Don River. When it approached the valley, it curved down to roughly follow the river’s course. It crossed the river via a bridge and eventually the railway tracks at a level crossing. Finally, it terminated at Leslie Street.

1860 Tremaine’s Map showing Old Cummer Avenue
Source: Old Toronto Maps
1968 Aerial showing course of Old Cummer Avenue.
Source: City of Toronto Archives

By 1969, the street was rerouted to curve north away from the river (which looks to have been straightened around this time as well). The street passed through a new wider bridge over the Don River and then under a railway overpass before eventually becoming McNiccol Avenue at Leslie Street.

1969 Aerial showing “new” Cummer Avenue under construction and Old Cummer Avenue.
Source: City of Toronto Archives

The old, orphaned course still exists in parts. The curved section lives on as part of the East Don Parkland trail, although not all of it follows the old path. The old bridge is in situ as well. The trail travels east through the hydro corridor where it terminates at the railway tracks. On the other side, Old Cummer Go Station and a hundred-metre long Old Cummer Avenue hold the old name.

Old Cummer Avenue, 2020
Source: Google Maps
Cummer Avenue, 2020.
Source: Google Maps
Source: Google Maps & Bob Georgiou

More reading: Scenes From East Don Parkland

Click here for the map below of “Old” Streets.

Source: Google Maps & Bob Georgiou

For more “Old” Streets, I created a sequel here.

Scenes From The Lesmill Office Park

Welcome to the Lesmill Office Park

The Lesmill Office Park is located in the Don Mills neighbourhood of Toronto. While on the surface this post-war collection of industries may be uninspiring, its history and current make-up is interesting.

The Lesmill Office Park, 2021.
Source: Google Maps.

The City of Toronto defines the Office Park’s borders as roughly the East Don River in the north, Leslie Street to the west, Don Mills Road to the east, and Bond Avenue and Canadian National Railway to the south (excluding parkland and residential areas). For the purposes of this article, only the area north of York Mills Road will be explored.

Office Parks and Employment Zones in Toronto.
Source: City of Toronto.

The Lesmill Office Park mixes light industry, offices, courier companies, and some retail to make for an eclectic combination of enterprises. In modern terms, it is an important employment area for the City of Toronto. Historically, it is an overlooked part of the post-war development and growth of Don Mills. Moreover, the fascinating part of the Office Park is its evolution from farms lot and how they continue to play into the modern fabric of the district.

The Lesmill Office Park with historic farm lots. The circles denote the locations of farmhouses.
Source: Google Maps & Bob Georgiou.

The Duncan Plot & York Mills Road

Beginning in the 1800s, the Duncan family owned 200 acres at Lot 11, Third Concession East of Yonge in the historic community of Oriole. In modern references, this was the north side of York Mills Road between Leslie Street and Highway 404. David Duncan in 1865 constructed a farmhouse which would be named “Moatfield”.

1860 Tremaine’s Map of York County.
Source: Old Toronto Maps.
Duncan, David, ”Moatfield”, York Mills Road, north side, west of Don Mills Road, 1905.
Source: Toronto Public Library
1956 North York Pioneers and Landmarks c. 1878, by Ted Chirnside.
Source: North York Historical Society

By the end of the 1950s, changes came to York Mills Road and the Duncan family lot. At Leslie Street, a British American (B/A) Oil Company service centre opened at 800 York Mills.  By 1960, the gas station expanded to occupy more of the corner. B/A was defunct by 1970; today there is a PetroCanada on site.

1947 Aerial of the future site of the Lesmill Business Park.
Source: City of Toronto Archives.
House and service station on the northeast corner of Leslie Street and York Mills Road, 1957. Note the B/A gasoline sign in front of the house.
Source: Toronto Public Library.

In 1960, industry came to this part of Don Mills. The Imperial Tobacco Sales Company of Canada and the Canadian Westinghouse Company opened on either side of the CNR tracks on York Mills Road. The coming of the railway to Don Mills in the late 19th century and early 20th-century was important in the future arrival of the Office Park. A siding served the former factory. Today, both factories no longer exist, being replaced in the 21st century by the York Mills Gardens mall and an empty lot seemingly ready for redevelopment, respectively.

1960 Aerial of York Mills Road, east of Leslie Street.
Source: City of Toronto Archives.
1969 Toronto City Directory showing York Mills, north side between Leslie Street and Don Mills Road.
Source: Toronto Public Library.

At 860 York Mills, a second gas station – Harry’s Shell Service – stood at the southern entrance of the Business Park at Lesmill Rd. In 1998, the land was rezoned from industrial to commercial use to accommodate a one-storey building. A City of Toronto report stated the properties in the Business Park were “under-utilized” and the proposed building was “to facilitate the articulation of this important intersection and serve to enhance the general appearance of the area” and “provided increased amenities to the area”. The adjacent Don Mills Car Wash at 862 York Mills was another early business of the Business Park. The structure still operates in its original use and used the Don Mills Car Wash name until about 2014!

The Moatfield House at 866 York Mills Road itself was impacted directly by redevelopment. In Don Mills: From Forest and Farms to Forces of Change, Scott Kennedy wrote by 1962, the Duncan farm was reduced to sixteen acres near the farm house. By this point, the property belonged to Kate Duncan, the widow of Gordon Duncan, son of David Duncan, the house’s builder. In 1972, Kate Duncan passed away. The Prince Hotel (later the Westin Prince, now the Pan Pacific) opened on the former Moatfield property on June 1, 1974.

The empty, derelict farmhouse was moved closer to York Mills Road to accommodate the development, but its survival was not secure. With the future of the Moatfield house in jeopardy, the Tzioumis brothers rescued the property in 1986 and moved it 300 metres north, where it operates as the the David Duncan House. The steakhouse still stands on the original Duncan plot from the 1800s. Both Moatfield and The Prince Hotel are Toronto heritage properties.

Gordon (son of David) Duncan House, 1961.
Source: Toronto Public Library.

Don Mills Road goes north

An important event in the creation of the Business Park was the northward extension of Don Mills Road from its terminus at York Mills Road. The latter road curved through the intersection. The idea was first proposed in 1961 at a cost of $3.75 million and was meant to accommodate the loss of Woodbine Avenue, which was absorbed into the new Don Valley Parkway. Land acquisition took place between 1962, with construction on the road, including new bridges over the East Don River and Highway 401 taking place in the following years. The Don Mills Road extension opened by 1966.

York Mills Road And Don Mills Road, 1963.
Source: City of Toronto Archives.
1963 Aerial of York Mills Road and Don Mills Road.
Source: City of Toronto Archives.
“New Bridge Takes Shape Over No. 401 Highway Where Don Mills Road Crosses”, The Globe and Mail, August 6, 1964.
Source: Globe and Mail Archives.

The Toronto Transit Commission’s Don Mills bus route began servicing York Mills Road in 1954. With the extension of the street, the 25 route also grew, even taking on an “A” branch in 1971 which serviced the business park. The 122 Graydon Hall bus took over in 1985.

1971 TTC Route Map.
Source: Transit Toronto.

Layers and layers on Lesmill Road

Lesmill Road was the first street to go up in the Business Park, being built north only to the Duncan property line in 1963. Warehouses, factories, and offices lined both sides of the streets, hinting at was to come.

1969 Toronto City Directory showing Lesmill Road, east side north of Leslie Street.
Source: Toronto Public Library

The origins of the Business Park lay in 1964 when the North York Planning approved a plan by Wretham Estates Ltd to develop 120 acres of land east of Leslie Street between York Mills Road and Highway 401 for industry. Wrentham Estates Ltd. seems to have been a real estate company spearheaded by industrialist E.P. Taylor which managed residential, commercial, and industrial properties. Taylor initiated the Don Mills project in the 1950s. It might be fair to say in this period “Oriole” as a descriptor for the area fell out of use as the community’s farms slowly started to disappear; it would be supplanted by Don Mills. The Wrentham Estates themselves was a residential and commercial project in York Mills around Bayview Avenue; the York Mills Shopping Centre was one of the by-products.

1957 Aerial of the area which would become the Lesmill Office Park.
Source: City of Toronto Archives.

For this reason, the Lesmill Business Park is/was also known as the Wretham Estates Business/Industrial/Office Park, although use of the name seems to have dwindled this century. The 1966 Annual Report of the Canadian Equity & Development Company (later owners of the Wrentham Estates Ltd) cited that 23.6 acres of the industrial park had been sold at $40,000 to $50,000 per acre. Some remaining 43 acres were expected to be sold over the next few years and all services had been installed.

Lesmill Road, seemingly a portmanteau of Leslie and (York) Mill(s), was constructed between 1965 and 1969. It was laid out mostly over the 19th century plots 12 and 13, mostly belonging to the Elliot and Hunter families (and as others as ownership changed).

1965 The Lesmill Business Park starts to take form.
Source: City of Toronto Archives.

Lesmill is lined with many factories on either side. As it curves towards the CNR tracks, a long-removed siding served a former Johnson and Johnson plant at 66 Lesmill. As one moves up the street, there is an interesting mix of businesses.

1969 Toronto City Directory showing Lesmill Road, east side.
Source: Toronto Public Library.

At the road’s northern end, Moatfield Park edges on a branch of the East Don and has a couple of neat tidbits. Although it named after Moatfield, the farm did not actually extend this far north. In 1985, a recommendation was made by the North York Historical Board to move and restore the derelict Duncan/Oriole Station on York Mills Road, which was ultimately rejected by the city (the old station was sadly and ultimately demolished). More interesting, the park’s soccer field was the site of a 14th-century Huron-Wendat ossuary, discovered in 1997. It is a reminder that before the Business Park and the European settlers before it, there was human settlement here.

Lesmill Road once terminated at Moatfield Park, at the line which divided the north and south halves of Lot 13, another Hunter family plot. In 1983, a Metro Transportation study recommended its northward extension to Leslie Street, one of several suggestions to alleviate road congestion in Toronto. In 1988, an Environment Assessment Study was conducted and the street was extended. The move provided another entrance to the office park, access to and from the highway, and alleviated congestion along Leslie Street.

1983 Aerial showing Lesmill Road
Source: City of Toronto Archives.
“Lesmill Road Extension”, Toronto Star, January 13, 1988.
Source: Toronto Star Archives.
1991 Aerial showing Lesmill Road.
Source: City of Toronto Archives.

Out of Place? The Locke and Goodwin Houses

At the north end of Lesmill Road off a driveway, two historic houses stand next to the on-ramp for the eastbound 401. They look out of place, and rightfully so: their contexts have shifted.

The first house is a Tudor Revival-style home built in 1933, informally named the Clark Locke House. Now with the modern address of 355 Lesmill Road, the house was called “Birches End”. The house’s namesake married into the family of former Ontario Premier George S. Henry, who held property here north to Sheppard Avenue. Scott Kennedy wrote Birches End was located “on a high point of land near the top of a ravine that contains one of the oldest stands of white pines in Ontario”.

The Locke House was historically accessible from Leslie Street. When Highway 401 was constructed in the 1950s, the Henry farm was split on either side of the motorway, including landing Birches End on the south side. The widening of the highway expropriated the property in the following decade. The house sat derelict and empty until it was saved by the Ontario Nature. The City of Toronto Forestry Department uses the house now. When Lesmill was extended in the 1980s, it became the driveway for the property. Perhaps it is a candidate for a future Doors Open.

1947 aerial of the Locke House.
Source: City of Toronto Archives.

Easy to miss but sharing the same address, the William Goodwin House stands beside the Locke House. It was built in 1845 and is not original to the property. It stood on Yonge Street in York Mills until the 1980s. Much like the Locke House, it fell into disrepair until it was saved and moved beside the Locke House. Its survival makes it the oldest standing house in North York.

Duncan Mill Road: New and Old

Today, Duncan Mill Road hosts an interesting collection of buildings, including two medical buildings (one of which lights up at night), the headquarters for Herjavec Group, a co-working space, and storage complex.

Duncan Mill Road was laid out in the mid-1960s at the same time as the other streets in the office park. Its naming seems to references the Duncan family, although their plot was not its direct vicinity (the mill part will be explained shortly). Running from Don Mills to Lesmill, its construction necessitated a bridge over the East Don River, which was completed around 1968. It is, however, not the first crossing here.

A former road was situated just north of the present one, which ran between Graydon Hall Manor to the east of the river and the farms to the west. This was on the north half of Lot 12, historically associated by the Elliots, but likely passed through different owners and subdivisions in the mid-twentieth century. The farm had a horse track on the plot.

1963 Aerial showing the Old Duncan Mill Road.
Source: City of Toronto Archives.

When one ventures into the valley of the Betty Sutherland Trail, a couple clues point to the old road’s former existence. The first relics are obvious – at least in the sense that they are visible. These are the “Duncan Mill Ruins”: a larger roofless structure containing a boiler and a smaller, square structure which house more elaborate equipment.

The origin of these buildings are unknown. Scott Kennedy speculated the larger building may be the remains of a mill from the Hunter property, which once may or may not be the same one seen in maps to the south of here. He also theorized the smaller “newer” building was connected to the 1930s Graydon Mall manor as its style references the mansion’s architecture (other writers have pinned it as a water pump for the house itself, but Kennedy does not seem to go as far to make that connection). The North York Historical Society speculated it was a water pumping station for the residents of North York.

A lesser known remnant of this old road are some concrete pads located south of the ruins on either side of the river. These look to be leftovers of leftovers: bridge abutments of the former bridge that ran through here! The leftovers were once more pronounced, as seen by these 2004 images. Today, the new Duncan Mill bridge looms over in eyesight of the site of the old bridge and its neighbouring relics.

1970 Aerial showing the new Duncan Mill Road and the old bridge over the East Don River.
Source: City of Toronto Archives.

Opposite the Betty Sutherland Trail, the Duncan Mill Greenbelt offers some neat surprises. A foot bridge travels over the East Don River. On the east side of the river, there is a baseball diamond, sandy volleyball court, and views of the river. Most oddly yet intriguing of all, some wooden stairs lead up to Duncan Mill Road. Their origin is unknown, but their existence is intriguing.

On the west side, more greenspace offers up a soccer field. There is an ascend up to Moatfield Drive, which is prominent at the Bayview Glen Independent School, whose stairs are built over the topography. The school moved into the Brutalist 1970s-era building in the 1980s. There are currently renovations on the side facing Duncan Mill. Across the street, a Moatfield campus was opened in 2014 using some excess space in a parking lot. The site of the school itself has a history which reaches back many generations.

Scott Kennedy wrote that the Hunters built a home on southern lot of plot 13 west of the Don River in the 1840s. It had a long driveway leading from Leslie Street which straddled the property line with the northern lot. A victim of fire, this house had a survived until 1961 when the property was under the Anderson family. A new house called Green Acres went up in its place and even had an address in the city directory: 85 Valleybrook Road. Much like Moatfield, Green Acres continued to stand even as offices and warehouses went up around it. It survived until the early 1980s.

Valleybrook Drive has a couple of notable modern landmarks. At 41 Valleybrook, there is the headquarters for SOCAN, an organization founded in 1990 to represent Canadian publishers and songwriters. When the structure was first built, it hosted BMI Music. Beside it at 1 Valleybrook, an interestingly-designed office building houses Parkin Architects, which seems to be the firm of famed Canadian modernist architect John C. Parkin. It also hosted a IBM plant too at one point.

1969 Toronto City Directory showing Valleybrook Drive.
Source: Toronto Public Library.

By the early-1980s, Moatfield Drive was added to the business park, running between Valleywood Drive and Don Mills Road and effectively completing the layout we see today. Interestingly, although it seems to be named after the Duncan farm, only a small portion actually runs through the old Duncan lot. In the 1980s, the first buildings went up on the street: the current Kraft Heinz office and Thales Group structures. Green Acres once stood in a parking lot adjacent to these buildings before the Bayview Glen School was built.

Aerial of The Lesmill Office Park, 1991
Source: City of Toronto Archives.

One newer structure is the headquarters for the Ontario Association of Architects at 111 Moatfield Drive. Although this building looks like a 21st-century construction, it opened in 1992 and was designed by Toronto architect Ruth Cawker. It is an interesting two-storey building with many windows and natural light. It too may be a good candidate for a future Doors Open.

Finally, the David Duncan House is situated at 125 Moatfield Drive. As mentioned, it was moved here in 1986, still on the original Moatfield lot, although facing Don Mills instead of York Mills. It is one of a few visible links of the Lesmill Business Park’s former life.