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The Bentway’s first phase begins at the west end, at Strachan Avenue, with an open-air theatre and performance zone.

Can people enjoy spending time under a busy expressway? As Alex Bozikovic writes, one look at the space that is becoming Toronto's newest public initiative will tell you that yes, they can

It's a public space – but not quite a park. It's located under an expressway, with an open-air theatre, public art, a walking trail and a skating rink.

This is the radical vision for a new public initiative in Toronto, and the Bentway – which was unveiled as "Project: Under Gardiner" two years ago, driven by an unprecedented $25-million donation – is moving toward opening its first phase in December.

And while it's counterintuitive, the Bentway also represents a new generation of public space: a mix of recreation, culture and social spaces that serve the needs of an evolving city while reusing tough scraps of the urban fabric.

"I think it will change how we look at public infrastructure across Canada," argues Julian Sleath, chief executive of the Bentway. "As the sites get the necessary repairs," he says, "they will become places where we enjoy spending time."

If the 1970s and '80s were the era to revisit urban ports for projects such as Granville Island and Harbourfront, this decade is when expressways and rail corridors, including Vancouver's Arbutus Corridor, become the focus for community-building. And the Bentway is the test case.

Can people enjoy spending time under an expressway? Yes: Once you've seen the space that is becoming the Bentway, it's clear that they can. Under the Gardiner Expressway on the west side of downtown Toronto, it's an outdoor area that is somewhat shaded, spacious – the highway is more than 15 metres off the ground – and surprisingly peaceful. It runs alongside the Fort York National Historic Site, cutting through a dense and fast-growing neighbourhood of residential towers. The Bentway is planned to stretch 1.75 kilometres; there are, the designers say, 70,000 people within a 10-minute walk of this zone.

"The delight for me," Sleath says, "is to create something that can combine performing arts, social and environmental activations, and be a place for the tens of thousands of people in this area to enjoy."

Located on the west side of downtown Toronto, The Bentway’s first phase runs alongside the Fort York National Historic Site, cutting through a dense and fast-growing neighbourhood of residential towers.

I toured the site recently with the landscape architects Adam Nicklin and Marc Ryan; their studio, Public Work, is designing the Bentway, and they are deep in construction as the project gains momentum for a winter opening. As we walked past the visitors' centre for Fort York, which already faces the area under the expressway, they explained the components of the project's first phase: a skating trail, 250 metres long to start, and a new building to serve it. An open-air theatre, with bleachers to seat about 250 and a lawn amphitheatre that could hold another 500.

The Bentway will commission its own site-specific works of visual and performing art, overseen by its director of programming, Ilana Altman; and it will partner with community and cultural groups of all kinds. More than 100 groups have expressed interest in partnering, Sleath says, "from a garlic festival to the National Ballet and the Toronto Symphony Orchestra."

The space itself is defined by huge structures of reinforced concrete, called "bents," that support the highway; Public Work's design uses these to divide the space into "rooms."

Toward the west of the site, earth movers were shaping the hills of the open-air theatre; utilities were going in to serve the new theatre structure, which will place bleacher seating on top of washrooms and storage space. The result will be a fully equipped and covered space for outdoor performance.

The potential of this unlikely space was what birthed the Bentway. A Toronto couple, Judy and Wilmot Matthews, were interested in making a large philanthropic donation to benefit public space in their city; and with the advice of urban designer Ken Greenberg, they turned their attention to this strip of land.

Since then, the project has moved at remarkable speed; vocal support from Toronto Mayor John Tory pushed city divisions to work together, streamline processes and co-ordinate their resources. "A lot of what is happening is just common sense," Ryan says. "Staff members at the same table, having open conversations, and other stakeholders, too, discussing shared benefits and figuring out ways to make things come to life."

Seating and a wooden stage will be among the few buildings added to the site in its first phase. New hardware clipped onto the “bents” of the highway structure will provide lighting and support for, as in this image, a screen.

The "how" of this project is important. Sleath's employer is the Bentway, a non-profit that has been set up to administer and program the space. While the corridor will be public and open 24/7, it is not technically a park. That structure allows the Matthews' money and influence – Judy Matthews is trained as an urban planner – to help the project move quickly and nimbly. "The entire modus operandi of this city for the last 50 years has been pulling things apart," Public Work's Nicklin says. "We've had to put them back together in six months."

It also allows the project to push the city toward unfamiliar goals, and to create a sort of public life that would have been unimaginable a decade ago.

In this respect, the obvious reference point is the High Line, an elevated rail-line-turned-park, which since its 2009 opening has become one of New York's most popular attractions. Can the Bentway be another High Line? Lisa Switkin, a landscape architect with James Corner Field Operations, who worked on the New York project, cautions that such comparisons can only go so far. "You can't use a cut-and-paste approach," she advises. "What makes the High Line special is its locale and its authenticity. We ask people to look at their particular place, and see what fits where it is."

Switkin and JCFO are now working on the Underline, a park in downtown Miami that – much like the Bentway – will fill space under an elevated expressway. "It's turning something that was seen as a barrier into a connector," she says.

This is almost precisely the language that the Bentway's proponents use to describe their work. And they share a concern with the High Line's founders about the social and economic impacts of what they are doing – which in New York included fast and intense gentrification. So: Who are these places for? And how will they change their cities?

To respond to that, the High Line's founders last month announced the High Line Network. The Bentway is one of 19 members in the association, which aims to make sure that the benefits of such projects reach the entire community. While the Matthews' gift is purely philanthropic – unlike some private donors to the High Line, they don't stand to reap real estate profits – the questions of park equity and access must be addressed.

But private initiative, unquestionably, raises new possibilities: integrating culture into the daily lives of city dwellers. "I have learned that art can be presented successfully in many different locations," Sleath says. "Some art needs to be carefully protected; but there's also the sheer delight of coming across something entirely unexpected."

What better place to do that than under a highway?