If only there were a bit more time . . .
That's a good ride . . . I took nearly 50 days in '93 from Washington, DC with "interruptions" for road work (mostly in Canada), floods (the Mississippi went high then), and some great scenery on a BMW K75S.
Did it again in 2009 from San Francisco on a KTM ADV 950. The Alcan is hard to get excited about, especially the Winnebago caravans. Use the interstates in the US and then try to "save" some for Canada. Push west to avoid the prairie in Alberta, etc.
BC is lovely, the Yukon sublime. You'll find lots of recs for the Dempster over the Dalton (haul road) but it might be tricky on the HD if there's weather. That would save you some mileage and add ALOT of scenery.
Good luck !
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