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Over the Rockies in the Winter!

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Hey everyone!
I have to travel from Eastern South Dakota to Boise, Idaho in the middle of February. I'm driving an F250 pulling an 18' cargo trailer (loaded). I'm wondering whether I should pass over the Rockies in Southern Montana or in Southern Wyoming? It seems like either route will take about the same amount of time, but I would appreciate your input as to which may be an easier pull and better roads.

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