Ok, family, I've taken a bunch of previous comments and suggestions into account, and I've done some research. Here is my first shot at an itinerary. Left some things out, focused on seeing what I can from the road but also making time.
All times listed are drive times and does not account for lollygagging or pump & dump stops.
Fountain Inn to Sundre: (total 2488 mi, ~40 hrs)
Day 1: Fountain Inn to Madison WI, 873 mi, 13:23
Day 2: Madison to Sturgis, 801 mi, 11:26
Day 3: Sturgis to Helena MT, via Cody WY and Beartooth Pass, 730 mi, ~12 hrs
Day 4: Helena to Sundre, 455 mi, 7:35 (plus however long the Mounties delay me at the border)
Sundre to Fountain Inn: (total 2860 mi, ~45 hrs)
Day 1: Sundre to Cohasset MN (family), 1122 mi, ~18 hrs
Day 2: Cohasset to Lynn (maybe a stop in Cushing WI), 680-840 mi, ~10:30 to 13:30
Day 3: Lynn to Fountain Inn, 521 mi, 8:30
Would love to know what you guys think, especially those who have traveled some of these roads.
Anyone from this forum in the close vicinity to Sturgis or Helena who might have a spot in the driveway for me to roll out a sleeping bag?
add another 12 hrs each way and you will be good. That doesn't include weather