We went into the USA by 'plane to Baltimore, up into Canada via Glacier National Park, rode up the Alaska Highway turning off into Skagway from the Yukon (Canada into USA), back to the Alaska Highway (USA to Canada), up into Alaska proper, rode around Alaska, back into the Yukon (Canada) and down to Haines (USA) to catch a ferry to take us down to Vancouver Island and then across Canada to Niagara Falls where we went back into the USA. No problem at all at any crossing, they asked a few questions but we didn't have any problems at all but officially you're only allowed 31 days (I think) out of the country on the same white card (the bit they give back to you when you first go in).
However, in '08 we went up to Nova Scotia and gave up the white card ('cos we didn't know any better) and when we came back into the USA, because we didn't have one we had to answer a few questions and buy a new one each for $6.00, but again, no problem, but that gave us another 6 months stay !
Be polite, tell the truth, smile a lot.
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