Did the trip on a 1999 Dyna Wide Glide couple years ago then last summer on a BMW F800GS from Winnipeg in three weeks both times. Hit hard across the prairies I was on secondary highways to Edmonton AB. Took day and half on the Harley.
If take I 94 across west you make great time Head north on north Dakota 52 into Canada head north from there.
From Winnipeg to Montreal can be done in three days its another day to New York. I was pushing hard then slowed down once I got to the Alaska Highway.
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