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So what does Winnipeg have going for it? On the surface, not much. This is a city that counts a difficult intersection (the aptly named Confusion Corner) as a famous landmark, which should tell you all you need to know.
The tourist brochures would point you towards the Manitoba Museum, an undoubtedly interesting collection of artifacts and historical pieces in the town centre. But I'm not much of a museum goer, so that was only going to keep me amused for a couple of hours.
But help was at hand. That friend I once travelled with was still living in Winnipeg and she'd offered to meet up for a drink. We were going to Osborne Village, she said, the artsy, creative side of Winnipeg that I only realized existed after I was told we were meeting there.
And that's when Winnipeg started to make sense.
You know how dodgy, rundown suburbs seem to become cool over time? How places such as Surry Hills in Sydney used to be no-go zones until the artists and musicians moved in and suddenly the people who wanted to be around artists and musicians followed suit?
Winnipeg is on the cusp of that transition. It was never dodgy - just dull. But it was also cheap and the government offered incentives for creative types to move in, so the artists and musicians packed up their vans, tackled Confusion Corner and settled down on the prairies, completely changing the city's landscape.
It would probably shock the customs guy as much as the rest of Canada, but the city I found is not just cold - it's cool. Who'd have thought?