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Standing at the Winnipeg airport last weekend, waiting for my flight home to Toronto, I could see the prairie out the window of the lounge. An unseasonably hot spell of fall weather had set the landscape to steaming, and a dense haze hung over the flat expanse of open fields. It was as if the earth were making one last warm, damp exhalation before falling asleep for the winter. The land feels different there. Unchanged by rampaging tides or the heaving of mountain ranges, the prairie is the sum of everything that has happened before, all sifted to sediment and remaining, somehow, underfoot.

It made me wonder if this is a factor in a quality that one finds in art from this region, a sense of the past haunting the present, the flickering undercurrent of memory and trauma. You feel it in the surrealism of the painter Ivan Eyre. You feel it in the purgatorial darkness of William Kurelek, who spent his formative young years here. And you feel it in the films of Winnipeg filmmaker Guy Maddin, whose new work-in-progress Only Dream Things I had seen the night before as part of Winnipeg Now, a beautifully crafted survey exhibition of the art of this city.

Maddin's new film installation is his most personal work to date, arising from his family's harrowing personal history. At 4, he lost his older brother, Cameron, who died suddenly at the age of 16. Guy was moved into his older brother's bedroom, inheriting his hobby cameras and audio recording equipment, as well as his National Geographic magazines, his shell collection and the other accoutrements of his life.

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For the Winnipeg Art Gallery show, Maddin has transported these things into the gallery, recreating the bedroom, and introducing a screen on the wall on which he is showing a film made from digitally distressed home movies shot by Cameron and his other family members. In Maddin's remix, we observe a teenaged Cameron on a trip to Seattle, his lovely girlfriend swimming and running on the beach, his mother slowly mounting a flight of stairs, the siblings playing on a wagon in the garden and Guy as a toddler scooped up in his big brother's smiling embrace. Several images are interlaced throughout – Charlotte Rampling recumbent and dreaming on a bed, and the French actress Ariane Labed drinking deeply, perhaps recklessly, from a little bottle. Is this a death potion, or a toast to life? Maddin has added to this visual sequence vintage intertitles evoking the classical drama of antiquity and superbly engineered sound gleaned from pop songs of the day, blended with excerpts from Cameron's amateur recordings of family voices and his own. The characters seem to call out to one another across an abyss of time.

On opening night, Maddin conducted the first of several filmmaking performances in this space, leading a team of pyjama-clad teenaged girls in a fantasy seance for the camera. Building on the Winnipeg tradition of paranormal obsession (Hamilton House, near where Maddin grew up, was once a world-famous centre for occult activity), he filmed the girls fondling the Ouiji board, lapsing into trances and spewing reams of gauzy ectoplasm. Maddin may interleave these new segments with the existing family footage, cross-pollinating the story of his own family with a broader regional history and inviting, too, the lengthening shadows of Greek tragedy to fall across his view of a suburban Winnipeg now lost in time. This may be the most revelatory thing Maddin has ever done. It's certainly, to my eye, the most beautiful.

Winnipeg Now, curated by Meeka Walsh and Robert Enright, is at the Winnipeg Art Gallery until Dec. 30.

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