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Depending on where you cross you're as likely to get hassled about a knife on the US side as much as the Canadian.
Yep I've crossed several times this year and the U.S. guys are harder to deal with than the Canadians.
I do not understand the 'crossing the boarder' multiple times. Peter Y.
Any non-whites in your group? Have them cross last in either direction. They'll take the longest to get the okay. Anyone with a past DUI/DWI? Put them in the back of the pack too. They might not be allowed into Canada. Passport or no passport.