This town is built on York. The word, that is. It’s everywhere. It’s a fort, a university, even a “royal” hotel. Other names and nicknames, like Yorkville and “Muddy York” are splashed all over our mental maps of Toronto, but the one place that probably isn’t on that map is the former City of York. It is, and was, Toronto’s forgotten borough, an underdog of a municipality that lived in the shadow of its bigger, richer neighbours (like Etobicoke and North York) until all were amalgamated into the Toronto megacity in 1998.

York is not easy to find, as it’s completely landlocked and asymmetrically shaped, with very few overt signs that you are, in fact, there. It roughly lies west of Bathurst, between St. Clair and Eglinton, to the Humber River and Weston area, with a few municipal tentacles reaching in various directions.

Except for the Heath Street entrance to St. Clair West subway, York is without its own subway station. York’s poor financial lot was due in part to its southern boundary with Toronto being established just north of the lucrative tax base of the St. Clair retail strip. However, starting from Eglinton West station — just outside the boundary — a rare, by Toronto standards, abrupt shift in wealth and demographics is visible.

Until the station, Eglinton Avenue does a gentle Forest Hill fade-out, with upscale boutiques and shops quickly replaced on the other side of the former municipal border by the jumble of independent businesses that characterizes many of Toronto’s less glamorous streets, like Danforth east of Pape, Queen Street in Parkdale and so many of those Scarborough strip malls. Beginning in earnest with the Celebrity Tough hair salon and Celebrity Roots and Culture Supplies next door, Toronto’s Caribbean community has established its own ethnic strip as dense as Chinatown or Little Korea, but much less celebrated.

None of this would win an urban design award for beauty — nor would most of York — but like those other jumbled-up strips, Eglinton provides cheap rent for all sorts of small-scale economic activity, some good (like the store selling “Church dresses, suits and hats!”) and some not so good (the inevitable cheque-cashing services that blight all lower-income neighbourhoods).

There are still traces of the old city around, most often in the form of vertical “York” park signs, often coupled with new “A City Within a Park” signs. At the corner of Eglinton and Dufferin, where tiny St. Hilda Square gets the double signage treatment, Vaughan Road is prevented from attaching to what was once a five-point intersection. Previously known as the Vaughan Plank Road, it connected Davenport (one of Toronto’s earliest roads) with Vaughan Township to the north of the city. It crosses York on a diagonal, like Rogers Road does just to the west, breaking with the standard Toronto grid just enough to throw off an untrained sense of direction.

The name York originally referred to the township established in 1850 that stretched from the Humber River east to Scarborough Township and from the lake up to what is now Steeles Avenue. As Toronto grew, it annexed communities in the township like Parkdale, Deer Park and Yorkville, continually shrinking York until the “Municipality of Metropolitian Toronto” was created in 1954, establishing the City of York with what was left over. In the final edition of the York Municipal Code — a sad book without a city — the preface boasts “York is a pleasant surprise in Metropolitian Toronto, with a future that holds promise!”

Eglinton and Dufferin mark what was once Fairbank, one of the many hamlets that were eventually consumed by Toronto’s growth. The name survives on a few buildings, like The New Fairbank Hotel, a stucco-clad “gentleman’s club” just north on Dufferin. It sits next to The Universal Church, an architectural atrocity that is best described as the Roman Coliseum built suburban style. Dufferin, from here north, is one of Toronto’s ugliest streets, one you don’t want to show visitors.

All along Eglinton, a handful of surviving Italian businesses hint that this was a third Little Italy, behind the College and St. Clair communities. However, as with those two more established areas, the Italians have been slowly evacuating, travelling up Dufferin to Woodbridge, just as Toronto’s Jewish population has been migrating from the Kensington area up Bathurst to Thornhill.

The area beyond Dufferin south of Eglinton is one of Toronto’s unique neighbourhoods. Though it has no defining style, and even the most passionate Toronto booster would not call it beautiful, the topography makes this area charming. Built on a series of hills and valleys, streets make sharp turns and dead-end abruptly, sometimes at a grade that looks too steep for cars. Toronto has been called “San Francisco upside down” because of its many deep ravines (as opposed to hills), but this part of Toronto could easily be “Little San Francisco” — though instead of multi-million dollar Nob or Russian Hill homes, the York counterpart has treeless lots with brick bungalows, rusting Buick Centuries and Pontiac Fieros parked out front and copies of the Toronto Sun in the blue boxes, tiny manicured lawns and lots of interlocking brick. There are numerous Mary Poppins–style views above rooftops and chimneys, as well as parks with secret escapes up outdoor staircases.

Back on Eglinton, before it slopes down into the Humber Valley toward the Etobicoke Skyline, there is a break in the continuous streetscape with a large plaza that includes a Canadian Tire and Shoppers Drug Mart. A busy café there with a proper espresso machine looks across the street at a rise in the land that exposes a strip of residential backyards in an almost obscene manner, as if the houses were caught with their pants down. Below, in a space carved out of the ridge, an Adult Video Plus does business next to the Ready Lube, itself adjacent to the Aromatic Sensation Massage Parlour — an accidentally appropriate combination. It’s a typical Canadian landscape, but perhaps one we don’t like to talk about.

When I reach Keele, I turn south and pass through a non-descript but still functioning commercial block — York is full of them. At Rogers Road, there is another strange architectural oddity, a multi-coloured apartment building on top of a huge concrete parking garage. It’s a little bit of Holland in Toronto, or someone’s Dutch nightmare, depending on one’s tolerance for kitschy landmarks.

A left on Rogers Road leads east, back into deep York. A complex five-point intersection where Rogers meets Old Weston Road and Watt Streets is a chaotic European-­
style mess of traffic that somehow works. On one corner the Nova Era café overlooks the traffic flow, as do a Pizza Pizza, a Petro Canada and a Portuguese restaurant. In so many upscale suburbs you can walk kilometres without finding services like these but York, despite its dowdiness, is still a real city.

Had York developed sufficiently before the age of the automobile, this could be one of Toronto’s greatest intersections, maybe even marking the centre of York. However, like the Caribbean strip up on Eglinton, York — or the idea of York — lives quietly tucked away in a corner of Toronto only the locals know about, asking to be discovered.
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