If he's going to drive across the continent, at least try to convince him to dip down into the US to do it. Better/faster roads, and he can stop in places like Chicago and Minnesota on the way (great cities in their own right, but would be cool to catch games there as well). This way it will only be mind-numbingly boring once you hit the Dakotas....doing it through Canada (especially if the weather is still bad) will get old a few hours after he leaves Niagara.
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