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Another Yorkville treasure going, going, gone to the condo boom


Its modest red brick exterior seems unremarkable in 2017. But in architecture, context is everything.

When York Square was designed by the upstart firm of Diamond and Myers in the mid-60s, international architectural and planning wisdom was that the city was a dangerous place, full of decrepit, overcrowded buildings best bulldozed to make way for the brave new world of urban renewal.

Favoured at the time were buildings set back from the street, surrounded by big lawns and plazas. Projects like St. James Town were replacing large tracts of Cabbagetown. There were few places to dine outdoors.

But in Toronto, a new generation of urbanists was questioning conventional planning wisdom. Jane Jacobs had just published The Death And Life Of Great American Cities, and made Toronto home. John Sewell was organizing against urban renewal in Trefann Court, and counter-culture activists, architects and community advocates started organizing around stopping expressways, heritage preservation and the benefits of infill development.

Yorkville was full of people protesting the established order, so where better for an architectural project to break completely new ground? 

“It began with Dick Wookey, who had bought the property and had not been a developer, so both he and we were starting out on a journey,” architect Jack Diamond commented in a recent interview. “We persuaded him not to follow the rules.”

York Square 1.jpg

Vik Pahwa


Old buildings were kept and adapted, mandatory setbacks from the street were ignored, and a square with long passageways and hidden and sheltered cafe spaces was created to allow people-watching. 

The eye-catching round windows, which Diamond acknowledges today might be considered “a desecration of the historic buildings,” were important in creating a landmark with visibility for the new retail uses. The approach inspired similar developments in the neighbourhood.

“The boldness of the approach was its simplicity and modesty,” says Diamond.

York Square put the firm of Diamond and Myers on the international stage. Jacobs was quoted in Progressive Architecture on the project. 

“Diamond and Myers have sensitively used the old buildings without trying to pretend they are something else they have made them not in the least bit quaintsy, but of our times.” She went on, “The uniqueness and promise of York Square, though it cannot and should not be copied in carbon, should be an example to all developers.”

York Square was the hottest commercial development in Toronto. Key early tenants were the Book Cellar and London’s Vidal Sassoon. In an era when women were burning their bras, Sassoon revolutionized women’s hairstyling, putting an end to sleeping on pincurls and hair rollers. The salon interior was designed by Diamond and Myers in collaboration with Michael Stewart of Muller and Stewart, who custom designed the furniture.

York Square was the first of three key projects by Diamond and Myers to demonstrate that new places could be created by repurposing old buildings and adding around them. The other two are Dundas-Sherbourne and the Hydro Block, just north of Baldwin, east of Beverly.

In the late 60s there were no heritage protection laws in Ontario. The only way to save a building was through public pressure and persuasion, which worked for Union Station and Old City Hall but not much else.

York Square was owned and operated by the Wookey family for over 40 years. 

But over the past decade, some well-intentioned provincial policies, such as intensification (with its commensurate property tax pressures), have come together to seal the fate of this rather magical place. By 2010, property tax increases had pushed rents above what businesses could afford, forcing the family to sell the property for redevelopment. 

A high-rise condominium development designed by Zeidler Partnership Architects has been proposed for the site. The proposal calls for total demolition of the square and most of the buildings but retains facades along Avenue Road and Yorkville – acknowledging York Square’s designation as historically significant under the Ontario Heritage Act. The project includes a new urban plaza opening onto Yorkville, as well as a community gallery space. The project was the subject of an Ontario Municipal Board hearing in January 2017. The OMB has yet to release its decision.

Interestingly, Diamond feels that the time may have come for a new project. In his view, the lessons of the place have been learned and Toronto is a very different place now than it was when York Square was built.

York Square 2.jpg

Vik Pahwa


Architectural Conservancy of Ontario (ACO) -Toronto hosts a celebration of York Square on -September 12, with a screening of the 1968 Yorkville riots documentary Flowers On A One Way Street, at York Square (148 Yorkville). The event is part of an ACO film project to record York Square’s unique story. Tickets $35 at eventbrite.ca.

Catherine Nasmith is a heritage architect and president of ACO Toronto.

news@nowtoronto.com | @nowtoronto

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