Excavating The History Of Toronto’s Avenue Road

City Living, Midtown, Real Estate, Yorkville / Summerhill / Rosedale


When you look at the composition of a city like Toronto, you tend to think about the streetscapes, housing stock, and community vibes. Equally important, but perhaps less considered, are some of the roadways, highways, and byways that define the momentum and accessibility of the city; they are not only essential to transportation but also play (and have played) a role in shaping and evolving Toronto’s Village neighbourhoods.

Take Avenue Road, for example. This lengthy artery spans about 9km, from Bloor Street north to just beyond Highway 401 to Bombay Avenue. It stretches through high density residential and commercial areas, all of which have experienced significant rebirth over the years, adapting to housing, retail, and corporate tastes and needs.


*”TimeShift” photo courtesy of Wikipedia Commons.


There are differing schools of thought as to how Avenue Road received its name, but the most giggle-worthy is described in “What Are The Origins Of Avenue Road’s Name?” where it says a British surveyor declared “let’s ‘ave a new road here” upon arriving at the construction site. In reality, the “Avenue” is likely a nod to its tree-lined, idyllic quality, which was commonly used naming similar tree-lined streets in England. There are other Avenue Roads in other cities, like Sydney, London, and Melbourne that possess similar qualities, backing this particular theory.

Avenue Road was originally constructed in an effort to divert traffic and improve traffic flow and access to downtown Toronto and it still serves this very purpose today, many decades later.

Here is a yellowed black and white photograph from 1890, looking south from where St. Clair Avenue intersects it now. That is Avenue Road on the left before the area north of the Rosedale neighbourhood was developed in any significant way.


*Courtesy of Toronto Public Library, (r- 2040).


And here is a pic that was also taken in 1910 when Avenue Road was first outfitted with a streetcar line. Beyond being turned into a transit throroughfare, you can see the signs of development, like asphalt roads and substantial power lines. You can just make out old City Hall in the distance:


*Courtesy of the Toronto Arhcives (Fonds 1244, Item 7072)


In the 1940s, the Hoggs Hollow Bridge served to extend Yonge Street, but this was incorporated in Highway 401 in the 1950s. The image below from the late 50s shows Avenue Road under construction from the point of view of Del La Salle College. Toronto was expanding at a surprising rate and both commercial and residential building was moving north quickly. As such, Avenue Road had to be widened to accommodate the extra traffic. (Additionally, by 1930, Canada was the world’s second largest builder and exporter of automobiles, so despite the growing public transportation infrastructure, the number of cars on the road was almost doubling every 10 years or so).


*Courtesy of Toronto Archives (S 0065, file 10034, id 0001)


In the 1960s and beyond, the streetscapes began to shift to reflect housing and retail cycles. This is because wherever residential housing appears, amentities soon follow to support it and the lifestlyes of the owners, promoting growth.



Check out this article, “What Avenue Road Used To Look Like In Toronto”, for more in-depth history, as well as some great photographs of the evolution of the roadway over the years. This story has some great pictures of Avenue Road during streetcar line construction and talks about the Benvenuto Mansion that was constructed at the tail end of the Victorian era, located at Avenue Road and Davenport. The land was subdivided a few times to build apartments and the mansion was demolished in the 1930s. The property is significant because it was the impetus for much of the development in the Avenue & Davenport area. Here it is in 1890, followed by the apartments that replaced it in 1926.


*Courtesy of Toronto Archives, Fonds 1244, Item 0328. 
[Photo taken in 1910 – the same year the streetcar track extended north to the mansion and beyond.]


[Photo taken in 2016]


I’m backtracking in time a bit now, but let’s talk landmarks! There are a number of notable landmarks on Avenue Road, in particular near where it intersects with Bloor. Storied ‘Church of the Redeemer’ was established as a satellite church to St. Paul’s Church in the late 1800s. As the congregation grew, the need for a new church edifice emerged. The location on what is now Avenue Road wasn’t the first choice, but the builders felt that it wouldn’t make much sense to build two large churches so close together, so they went a little further west.


*Photo courtesy of the Toronto Archives (1924)


The first service was held in this church in 1879 and was designed in the High Victorian Gothic style, which we see in a number of pockets around Toronto. It is an active parish to this day and is well-known for its outreach efforts in Toronto. It is pictured above, decades later, in 1926).

Here is a post with some excellent photos showing how the area has changed over the centuries, with it looking almost rural in the beginning, despite its very urban location: “Toronto’s Church of the Redeemer, Avenue Rd. and Bloor”.



On the northwest corner of Bloor Street West and Avenue Road, is the tony Park Hyatt Hotel, built between 1926 and 1929, although construction of the opulent interior was halted in 1929 because of financial constraints during the Great Depression. Construction resumed in 1935 and opened for business in 1936. In addition to lavish hotel amenities and rooms, the building contained residential apartments.  Renovations and new construction continued over the decades, including the addition of a tower. Today, as it has been since its inception,  it is considered one of the finer hotels in town and is an integral part of the Toronto skyline. The hotel was closed in December of 2017 after it was announced that the property would be redeveloped, including a restoration of the historic south tower on the corner of Bloor and Avenue Road. In April 2019, Oxford Properties – who acquired the property in 2014 for $90M – announced that the revamped structure will include “About 20,000 square feet of retail space located at the base of the tower, with about 10,000 square feet at street level as well as an additional 10,000 square feet upstairs. The second-level retail will boast double-height ceilings with the opportunity for 30-foot heights within a mezzanine level with dramatic arched windows, according to Oxford Properties. With about 100 feet of frontage along Bloor Street West and about 100 feet along Avenue Road, the retail space will offer considerable exposure.” – Retail Insider  Construction is scheduled to be completed early 2020.


*Photos courtesy of Retail Insider & Oxford Properties


And, of course, you can’t discuss Avenue Road and Bloor without mentioning one of Toronto’s most notable landmarks: The Royal Ontario Museum! Read all about the city’s preeminent cultural institution here!


*Photo courtesy of BlogTO


There is something truly unique in being able to wander in present day down roads that our predecessors have. The rich history is embedded and integrated with the emergence of amenities to support lifestyle today without forgetting the past.

If you see yourself living in Toronto’s epicentre of luxe – taking your place on stately Avenue Road – with the everyday amenities of Yorkville chic, the retail paradise of Bloor Street’s ‘Mink Mile’, the cultural engagement of Toronto’s premier institutions, and the lifestyle benefit of easy connections to all points north, south, east and west – then this ‘bright lights big city’ location will surely tick your ‘location, location location’ box. When you live near Avenue Road and Bloor, you only have to step out your door to be in proximity to daily necessities, weekly sojourns and ‘whenever you fancy’ cultural and educational destinations! Seriously, within a one block radius you can cross the thresholds of the Royal Ontario Museum, the Royal Conservatory of Music, the Gardiner Museum, the Bata Shoe Museum, and the Toronto Metropolitan Reference Library!


Looking for a home that enriches your current lifestyle with a rich history? With a multi-disciplinary education in housing and great knowledge of the history of Toronto’s neighbourhoods, my team and I are here to help!


Thanks for reading!


– Steven

Steven Fudge, Sales Representative
& The Innovative Urbaneer Team
Bosley Real Estate Ltd., Brokerage – (416) 322-8000

– we’re here to earn your trust, then your business –

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*Title Image Courtesy Of Toronto Archives, S 0071, Item 6776.


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