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Jeff Thomas, Where do we go from here? 2013. Photo Intervention. Photo: Will Pemuliswill pemulis

Picasso said his art was a sum of destructions. The same could be said of modern cities, where visions of the future – sometimes clear, often not – continually challenge and replace the built environments of the past.

In Land|Slide Possible Futures, an ambitious show of installation art at Markham Museum, 30 artists set out markers of a past we are already forgetting and a future we can't yet see. Janine Marchessault, the York University film and media studies professor who curated the exhibition, links it to Marshall McLuhan's notion of art as a probe that jars us into perceiving environments that feel normal but that may be far from natural.

The show is well-situated, at a cluster of heritage buildings in a designated greenbelt city of rapid demographic change, where land-based occupations are being displaced by high-tech jobs. Markham Museum is itself a symptom of displacement: Its 30 heritage buildings were all rescued from development elsewhere and set down here in a village-like grouping.

But this particular village never existed: Its train station never welcomed travellers to this spot, and its sawmill is actually an old barn building in which the museum installed vintage milling equipment. The grounds include a mini-golf course featuring small replicas of demolished local structures, as well as isolated display cases for items such as a length of stovepipe. Attractive and interesting as many of the buildings are, a whiff of Dada clings to the site.

In this camp for architectural refugees, "site-specific" art is an elusive notion. The 30-odd artworks nestle inside their temporary homes with varying degrees of respect, engagement or alienation, while grappling for the big story that the Markham urban adventure invites them to tell.

The show's most haunting piece refuses to let us into its site at all. The video loops of Phil Hoffman's Slaughterhouse can only be seen by peering into a sealed shed through knotholes in the grey wood. His stories, buttressed by overlapping audio, include tales of his family's 30-year meatpacking business, and of a First Nations woman who petitioned Queen Victoria for the return of land taken from her. Hoffman's past is a place of hidden or secret knowledge that you have to prise out like a spy or eavesdropper.

Julie Nagam also digs for a buried past with singing our bones home, installed in the museum's wagon shed, where a ghostly wigwam and audio loop of First Nations songs hint at all that was pushed aside by the wagons' owners. Jeff Thomas's Where do we go from here?, installed on the side of a railway car, mashes up tourism and displacement in a series of large colour photographs of a wooden Indian – no other term for it – posed at various rail stations, with captions such as "Are you from around here?"

Several artists focus nostalgically on the hand skills and ingenuity of former times. Aron Louis Cohen's Markham Almanac documents the creation of a pamphlet Cohen printed on an old letterpress with paper from flax he grew himself. Skyhill Collective's The Textured Structure is an unwinterized hut made using several old-time construction methods, and Frank Havermans's untitled metal sculpture pays homage to the hoist pulleys that keep it suspended from the side of a heritage barn.

Cohen's piece is also about how we've lost touch with the land and organic cycles, a theme cleverly explored by Iain Baxter&'s whimsical Markhamaze. This elaborate maze, cut into grass, allows you to cheat and make shortcuts. That one feature says so much about our whole relationship to agriculture in the age of chemical fertilizers.

Other artists invite us to engage with simulated nature, embodied by Gregory's Sun Suckers, bird-like gizmos by Ken Gregory that use energy collected in their solar-cell tails to produce cyborgean birdsong. The 50 flower-shaped resin sculptures of Mark-David Hosale's Homunculus Agora (h.a.) use light, sound and sensors to mimic organic rhythms, while outlining the shape of the greenbelt that runs through Markham.

The most overtly urban pieces on display are Laura St. Pierre's Urban Vernacular, an arresting backlit image of an ad-hoc shelter in a parking lot, and Upper Village 2, a new pomo condo tower by Greenpark that looms over the whole museum. The building was going up as Marchessault was planning her show, and she tried and failed to interest the developer in lending its surface for video projections. Too bad – that brash exterior says more about the future of Markham than any of the works in the exhibition.

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