Depending on the wait times at the border, it's usually 3 hours between Winnipeg and Fargo plus border time. It's about 3 hours from Bismarck to Fargo and about the same to the Montana line. We have driven straight from Seattle to just before Montana line and then an extra long day to drive home. Hotels are tough in eastern Montana and western North Dakota but if you can get a room lined up in advance, that is best. Medora, ND is off season until Memorial Day and may be a good stop or else Dickinson or Bismarck. With 2 overnights I assume you could make it into North Dakota easily that next day. Good luck!
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