Kensington Avenue — which runs north-south between Dundas Street West and Baldwin Street — was one of the first streets created in Kensington Market and now serves as an eponym for the entire neighbourhood.

Much of Kensington Market was laid out by the Denison and Baldwin families during the 1830s-1850s. The Denisons were an upper-class Anglican family from Yorkshire who arrived in Toronto in 1796 and built the nearby Belle Vue estate in 1815.

The Baldwins were an upper-class Protestant family from Ireland who arrived in Toronto and laid out nearby Spadina Avenue between the 1810s-1830s and constructed the Spadina estate in 1818.

Over the following decades, the Denisons and Baldwins began subdividing land holdings and laid the foundations for the development of the surrounding neighbourhoods.

Kensington Avenue was originally known as Eliza Street (pre-1858) and (Upper) Vanauley Street (1858-1888/1889). Further information on the evolution of the street name has been included below.

Early versions of Kensington Avenue appear in James Cane's Topographical Plan of the City and Liberties of Toronto (1842) and Sir Sandford Fleming’s Topographical Plan of the City of Toronto (1851).

Russell Creek (also known as Simcoe Creek) bisected the street underneath the present-day intersection of Kensington Avenue and St. Andrew Street on its southeastern course through the area.

The creek was buried and sewered in the mid-19^th century. On some days you can still hear it flowing under the intersection.

Between approximately 1837 and 1894, the east side Kensington Avenue just south of St. Andrew Street was home to the Spadina Brewery.

Established by John Walker during the 1830s, the Spadina Brewery was the first business in what became Kensington Market. The brewery used Russell Creek — which ran directly through the property — as a water source.

The Spadina Brewery was one of eight breweries in operation in Toronto as of the Rebellions of 1837.

Early customers of the brewery included the Denisons, nearby cavalry and militia troops, and the St. Leger Racecourse (located just to the east of Spadina Avenue a short distance south of College Street).

Jordan St. John notes in Lost Breweries of Toronto (2014) that the Spadina Brewery experienced numerous challenges during its operation including contaminated water in Russell Creek as development (including agricultural and otherwise) intensified upstream; poor and hard-to-maintain connections to nearby markets including the population centre of Toronto (to the southeast) and the large military Garrison (to the southwest) — particularly during its early years; competition from larger breweries (including Gooderham and Worts); and complaints about noise and odours from nearby residents as residential development intensified in the surrounding neighbourhood from the 1850s onward.

There were at least 8 owners of the Spadina Brewery over its almost 60-year history. By the mid-1850s, it had been renamed The Brewery.

The Brewery ultimately closed during the second wave of (re)development of Kensington Avenue in the 1890s. The site was later developed with houses, as well as other commercial and industrial enterprises (such as Kensington Packing and St. Andrew's Poultry).

The former site of the Spadina Brewery — largely situated on what is now 17 and 23 Saint Andrew Street, as well as a few of the surrounding Kensington Avenue houses’ backyards — has been identified by City of Toronto Heritage Planning as having archeological potential.

I have been advocating for several years that an archaeological assessment be undertaken of the 17 and 23 Saint Andrew Street properties during any potential redevelopment and that any redevelopment of these properties include commemoration of Russell Creek and the Spadina Brewery.

Prior to 1858, Kensington Avenue was known as Eliza Street. The street was named for either Elizabeth (Eliza) Eleanor Denison (1802-1849) — the third wife of George Taylor Denison (1783-1853) from 1833 until her death in 1849; or Elizabeth Russell (1754-1823) — the half sister of Peter Russell and an early landowner in the district.

By 1842, approximately 6 small houses had been built along the street. Research is ongoing to identify the residents of the street during the 1840s. By 1855/1856, the residents of the street included the brewery owner, a broom maker, a bricklayer, a builder, two carpenters, a pensioner, and two widows.

Of additional note is that Eliza Street was another early name of Ryerson Avenue — located in Alexandra Park to the southwest. Street names in this area were frequently changed and/or recycled during the 19^th and early 20^th centuries.

By 1858, the name of the street had changed to (Upper) Vanauley Street and the number of houses had increased to 18 ± 2. Another subdivision plan for the remaining lots on Kensington Avenue, Baldwin Street, and St. Andrew Street area was registered by John Ritchey in September 1861 (with this plan showing Russell Creek still flowing on the surface through the area).

These early, pre-Confederation houses were largely wood frame and roughcast houses with a few brick houses near the brewery and northern end of the street. These represented the first wave of development of Kensington Avenue.

The name (Upper) Vanauley Street was derived from the name Macaulay. Dr. James Macaulay arrived in Toronto with Lieutenant Governor John Graves Simcoe during the 1790s and served as the Garrison Surgeon for York. For his service, he was granted Park Lot 9 in the 1790s.

Park Lot 9 was bounded by Queen Street, Bay Street, Bloor Street, and Yonge Street. The Macaulay family subsequently established Macaulaytown — Toronto’s first suburb — on the southern portions of Park Lot 9 and neighbouring Park Lot 10 during the 1830s.

Macaulaytown subsequently became a haven for Black residents arriving in Toronto via the Underground Railroad. Macaulaytown later became known as St. John’s Ward or The Ward.

The spelling of Vanauley Stret varies greatly across time with variations including: Vanaulay, Van Auley, Vanauly, etc. Terauley Street — one of the former names of Bay Street — was another derivative of the name Macaulay.

While Upper Vanauley Street ran north of Dundas Street West, Lower Vanauley Street ran between Queen Street West and Dundas Street West to the immediate south.

Vanauley Street and Vanauley Walk in Alexandra Park maintain the original name, albeit the course of the street nearest to Dundas Street West was significantly altered by the housing projects built during the 1960s.

During the mid-1880s through mid-1890s, virtually the entirety of Upper Vanauley Street was demolished and redeveloped. This was the second wave of (re)development and brought about the extant streetscape of largely Bay and Gable houses now associated with Kensington Avenue.

Kensington Place (originally Mackenzie Place) and Fitzroy Terrace were created during this period and contain rows of cottages that were home to working class residents.

One of the few properties in the vicinity pre-dating this second wave of (re)development is likely 3-3A Fitzroy Terrace — which was bult in 1871 and which originally fronted Kensington Avenue prior to the construction of 20-22 Kensington Avenue in 1889/1890.

During the late 19^th century, the residents of Kensington Market were largely from the British Isles and Christian. (Upper) Vanauley Street was renamed Kensington Avenue in 1888/1889.

This renaming paid homage to the affluent London district of Kensington and would have appealed to the largely British residents of the street while simultaneously increasing property values for developers and property owners with largely British-Canadian capital.

Many other street names in the surrounding area during this period were derived from places in the British Isles, such as Oxford Street, Cambridge Street (now Nassau Street), and Clyde Street (now Baldwin Street).

Similarly, St. Andrew Street was named for the patron saint of Scotland and nearby St. Patrick Street (now Dundas Street West) was named for the patron saint of Ireland.

Within the first two decades of the twentieth century, the British began moving out of the area. During this era, many Jewish families and residents — largely from Central and Eastern Europe — began moving westward from St. John's Ward into Kensington Market.

By the early 1910s, Kensington Market had become a Jewish district.

On the evening of 14 July 1913, a riot erupted at the intersection of Kensington Avenue and Dundas Street West after Rev. Henry Singer — a Christian missionary who had previously been accused of using anti-Semitic slurs — began an open-air sermon in attempts of proselyting the Jewish residents.

For several months prior, the Jewish residents had voiced annoyance and frustration at these missionaries' intrusive activities and had had requested that such activities be ceased.

Several thousand individuals participated in the riot and five residents of Kensington Avenue were arrested by police.

A subsequent letter to the editor written by Isadore Markus and published in The Toronto Daily Star a few days after the riot reported that an estimated 99 per cent of Kensington Avenue was Jewish as of that point in time and accused the police of displaying prejudice in their response.

Of further note is that a similar riot — also caused by Christian missionaries preaching and proselytizing in a Jewish district — had occurred two years prior in June 1911 at the corner of Bay Street and Dundas Street West.

It was during the early twentieth century that modifications occurred to many of the Kensington Avenue buildings — including the creation of commercial spaces within the buildings, the construction of new storefronts, and the subdivision of some single-family dwellings into apartments or boarding houses.

This resulted in the emergence of Kensington Avenue and adjacent Baldwin Street as a commercial district that became known as "The Jewish Market."

The commercial district consisted of both the aforementioned brick-and-mortar shops, as well as a lively sidewalk market consisting of cart- and stall-based vendors.

Early articles describing the commercial district refer to it as being the busiest market in Toronto and as having Old World aesthetics.

The residential-to-commercial alterations to many of the Kensington Avenue houses and the emergence of the sidewalk market represented the third wave of (re)development of Kensington Avenue.

By July 1925, The Globe newspaper was referring to the sidewalk market as "The Kensington Market" in addition to calling it the "Jewish Market." 

In August 1931, The Globe noted the "curbs are livelier than the small shops that line the streets … the merchant does not need a shop, in fact; he may set up a business on the front lawn or on the doorstep, and business comes" and that "every small shop seems to contain enough for a market in itself." 

By 1937, over two dozen shops had been "jammed tightly into the north end of Kensington Avenue" alone with these shops offering a diverse range of goods and services (from groceries to hardware to clothing to second hand goods — and everything in between).

By the 1930s, the commercial district had begun to expand westward. Like Kensington Avenue and Baldwin Street, Augusta Avenue was not originally a commercial thoroughfare. Augusta Avenue was incorporated into the business zone of the neighbourhood during the 1930s.

Diversity was noted to have been an early (and remains) an important aspect of Kensington Market.

In August 1931, The Globe noted that "somebody will one day paint a colour study from this portion of Baldwin Street" — this is now apparent both with the ongoing neighbourhood studies (such as the Heritage Conservation District) and the Baldwin Street Street Murals.

Other aspects of Kensington Avenue and Kensington Market have remained the same over the past 90+ years.

In May 1932, The Globe noted that "customers without exception come on foot or their small purchases […] an automobile or a vehicle, unless it is a handcart, is rarely seen on the street." 

However, by August 1937, The Globe noted traffic issues in the neighbourhood where "cars and trucks blocking the roadway […] trucks rumble down the street, hold, unload merchandise while the traffic jams and swells out behind them […] car horns blast and motorists yell."

In 1951, municipal planners attempted to mitigate the traffic issues by instating numerous one-way streets in Kensington Market — including Kensington Avenue.

However, again, in June 1957, The Globe noted "the monumental traffic jams of past years are still as monumental as ever in spite of one-way streets" and encouraged "the wise shopper [to] leave [their] car on Spadina or College and walk in." 

These same traffic issues are apparent within the neighbourhood as of 2023. The proposal to create pedestrian only zones within Kensington Market — in addition to the popular Pedestrian Sundays — have been a significant source of community discussion in recent years.

The Globe and Mail also noted that distinct districts had emerged within Kensington Market by the late 1950s: the poultry section was along Baldwin Street from Kensington Ave to Augusta Avenue and on St. Andrew Street; the produce section as on Augusta Avenue from Wales Avenue to Oxford Street; the dairy section was on Kensington Avenue from between Baldwin Street to St. Andrew Street; and second hand shops were on Baldwin Street and nearby D'Arcy Street and Henry Street (in neighbouring Baldwin Village).

These distinct districts have waned over time, albeit some legacies remain — such as Global Cheese (76 Kensington Avenue) which was established in 1970 and is now Toronto's longest running cheese shop.

In the post-World War II period, Kensington Avenue underwent a number of further changes. One of the most prominent was the construction of Lottman's Imperial Bakery at the south-eastern corner of Kensington Avenue and Baldwin Street during the mid-to-late 1940s.

The Lottman family had originally established their bakery on the north side of Baldwin Street (at 172 Baldwin Street) in the early 1920s.

This early bakery was an important meeting place for the Jewish women of Kensington Market who would meet and use the large ovens to keep their cholent warm overnight for Sabbath.

The new, 3-storey bakery — which opened in 1947 — allowed Lottman's to expand their operations and was one of the first bakeries in Toronto to use a mechanical conveyor belt and mechanized oven.

The Lottman's bakery closed in 1984. Its significance to the Kensington Market area and broader Jewish communities of Toronto has been profiled by the Ontario Jewish Archives in their Storefront Stories project (see here).

The bakery building remains on the corner and is now overclad in white siding. The upper levels later became an after-hours club and have since been renovated into residential lofts, whereas the ground floor has been subdivided into several smaller storefronts.

Other postwar developments include the construction of small-scale commercial and office buildings — including several small malls — on the west side of Kensington Avenue north of St. Andrew Street during the 1960s-1990s.

These are representative of the fourth wave of (re)development of Kensington Avenue.

By the 1950s and 1960s, new diasporic groups began to arrive in Kensington Market. These included Portuguese (including Azorean), Italian, Afro-Caribbean, Latin American, East Asian, and East Indian communities.

From the 1970s onward, Kensington Market became a hotspot for Toronto’s punk and counterculture scenes.

Two important LGBTQ2S entities: The Body Politic and Glad Day Book Shop also called Kensington Avenue home in 1972-1973.

In 1972, 4 Kensington Avenue was purchased by Amerigo Marras and Suber Donald Corley — a gay couple. Marras was an Italian-Canadian artist and Corley was a Vietnam War Draft Dodger. The couple established the Kensington Arts Association and opened an art gallery on the main floor.

They later advertised rooms to rent to other gay men and Jerald Moldenhauer, John Scythes, and others moved into the property.

Through this, 4 Kensington Avenue became an early home of Glad Day Book Shop and The Body Politic – both of which were based out of an unheated rear addition of the building.

Glad Day Bookshop was founded by Jearald Moldenhauer in 1970. It was Canada's first LGBTQ2S bookstore and is now the longest running LGBTQ2s bookstore in the world.

Niko Stratis in Glad Day Books and Café (West End Phoenix, 2011) notes that during the 1970s, Moldenhauer would "walk the streets with books in his backpack form one meeting space to another, doing whatever he could to help bring queer literature to the people who needed it."

The Archives Association of Ontario notes that "the Body Politic was Canada's gay liberation newspaper that operated from November 1971 until February 1987, publishing 135 issues. Not only were they a newspaper but they were an activist and organizing group of individuals who initiated many rallies, conversations, participated in many conferences, and fundraising initiatives within the Canadian and international lesbian and gay communities."

During this period, the Cecil Street Community Centre was the home of the Community Homophile Association of Toronto – an early LGBTQ2S rights group.

Baldwin Village was also a major hotspot for Vietnam War Resisters and Draft Dodgers living in Canada. Toronto's first Pride event occurred in 1971 and was coordinated by activists working from nearby Cecil Street.

The Body Politic and Glad Day Bookshop were evicted from 4 Kensington Avenue in 1973 after Gerald Hannon – a gay liberation activist and author and member of the Collective – published a controversial newspaper article which generated significant media controversy.

The two organizations later moved to Cabbagetown South.

The 1970s and 1980s saw the emergence of Kensington Avenue's arts, fashion, design, and vintage boutiques. These boutiques are largely distinct from the second-hand shops of the early-to-mid twentieth century.

One of the first vintage boutiques on Kensington Avenue was Courage My Love (14 Kensington Avenue) which opened in 1975 and is now the longest running boutique on the street. Kensington Avenue has since emerged as a popular hub for this class of boutiques.

In 2006, Kensington Market was declared a National Historic Site of Canada. Subsequently, in March 2015, the City of Toronto launched the Kensington Market Heritage Conservation District with the Heritage Conservation District Plan endorsed by the Toronto Preservation Board in September 2017.

The Heritage Conservation District Plan remains under study and development as of April 2023.

In more recent years, the Kensington Market Community Land Trust has achieved success on Kensington Avenue. In June 2021, the Community Land Trust was able to secure ownership of 54-56 Kensington Avenue — a 3-storey building containing 12 existing residential units and 5 commercial spaces.

However, Kensington Avenue may be under increased threat in the future. Adjacent high-rise developments have emerged along nearby Spadina Avenue and Dundas Street West.

In early 2023, reports emerged that real estate firms may be eyeing properties along Kensington Avenue and St. Andrew Street for potential land assemblies. Steps should be taken to protect this diverse and unique Downtown Toronto street.