I pulled my trailer from San Antonio to Great Falls on that exact route 3 years ago in April.
Your only hurdles will be seasonal weather. I encountered tornado warnings and severe thunderstorms near Amarillo, and heavy snow near Denver.
There were wind warnings near Cheyenne, but the wind was much lighter than predicted.
Billings to Great Falls watch for wildlife on the highway.
In July of the same year, I drove a U-Haul truck on the same route, weather was much more friendly, but almost tagged a dear about 65 miles from Great Falls.
I travelled it in three days each trip, 5 days will be very comfortable driving.
On one of your legs, you might find going to Cody, Wyoming to be worth your trip, the Buffalo Bill museum is on of my favorites!
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2011 Dodge Ram 2500 Cummins
2012 Starcraft Autumn Ridge 297 BHS
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