Wouldn't border patrol check against the watchlist? Canada at least knows if you're on the list of concealed handgun permit holders.

I guess with enough forest to sneak through and a "clean" buddy to drive through the borders and pick you up, you'd make it. This kid did it, and he was one of the first big BC Bud smugglers: http://www.rollingstone.com/news/story/7683923/kid_cannabis