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Eastbound traffic from the Gardiner Expressway exits at the Jarvis St. off ramp on March 10, 2021.Fred Lum/the Globe and Mail

Something strange, unexpected and kind of neat is happening to the Gardiner Expressway.

The hulking elevated highway was built in the 1950s and 1960s at the behest of Frederick “Big Daddy” Gardiner, the domineering chairman of Metropolitan Toronto. Ever since, the roadway everyone simply calls “the Gardiner” has loomed like a great grey wall at the south end of Toronto’s downtown, cutting the city off from one of its natural glories: its island-girded harbour.

But over the past decade or so, the booming city has advanced southward to fill up much of the vacant and underused land on either side of the expressway. Office and condominium towers have sprouted to its north and south, creating a new, vitally urban neighbourhood, the South Core. Buildings now flank it for most of the central stretch, with more going up all the time. Travelling it by car is like passing through a canyon with walls of glass and steel, a thrilling big-city experience (if you’re not stuck in traffic).

This has changed the effect of the Gardiner completely. Once it stood alone, dominating the landscape. Now, with its enveloping curtain of high rises, it is barely visible from many vantage points. In effect, the Gardiner is disappearing. With bustling city life going on all around it, with streams of pedestrians passing beneath it on their way to work and home, it no longer stands as a psychological barrier between the city and the waterfront.

That in itself is great news. Toronto neglected its waterfront for decades. That is now changing as the long-promised redevelopment ramps up, with playful new parks and neighbourhoods. The fading of the Gardiner eases the transformation.

Something even more hopeful is happening underneath the Gardiner. The underside of an expressway is an unlovely thing. Huge pillars support a roof-like car deck. Traffic roars by above. But creative minds are starting to see this dead zone not as an eyesore but an asset.

A quirky park, the Bentway, opened under a part of the Gardiner in 2018. It was an immediate success, drawing throngs to its skating trail, splash pad and landscaped paths.

There are plans to extend it to the east and west. One part of the vision calls for a whimsical pedestrian bridge suspended under the expressway and held up by cables. A park to be created close by is to include an interactive waterfall and an artificial hill with views to the lake.

The parks are only a start. A handsome government liquor store has opened under one section of the expressway, as if that were the most natural place in the world for a liquor store to be. In the same area, near a newly opened supermarket, developers are hoping to build a shopping complex with underground floors. Visitors will see the exposed foundations of the Gardiner’s massive pillars. An artist’s conception of its above-ground spaces shows musicians playing, people walking their dogs and reflective shapes slung from the expressway’s underside to brighten the area.

All of this is part of a wider movement to find new uses for aging industrial buildings and bits of urban infrastructure. Instead of tearing them down or leaving them to rot, cities are turning them into lively public spaces. The most famous example is New York’s High Line. It draws throngs to the innovative park built on an abandoned elevated railway line. Across the East River, Brooklyn is planning to enliven the spaces underneath an elevated highway, Bentway style. Miami, too, wants to create a linear park and public-art destination under its Metrorail commuter line.

The effort to transform the Gardiner is the most ambitious of these projects. It may end up being the most ambitious anywhere. A big, costly renovation of the aging expressway itself is also under way, spurring city planners and urban thinkers to seize the opportunity to exploit the spaces under and around it. A further spur comes from the waterfront redevelopment push and a plan to rethink nearby Exhibition Place, home of the Canadian National Exhibition. Architects, artists, developers, park people, city councillors – everyone is excited about the possibilities.

It is all quite marvellous and, yes, unexpected. If you had said in 1975 that the Gardiner would one day be flanked by glittering skyscrapers, that people would be skating underneath it and that its shadowed underside would one day become a place to display public art and creative landscaping – well, you would have been laughed out of the room.

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