We spent a little over a week in Madison Campground at Yellowstone with the pup in 2019. We did this route as part of the trip (not towing the PUP though lol)
One of the most spectacular trips I've ever been on. Heck, probably the MOST spectacular.
When I was researching road conditions for a pop-up camping trip through Quebec and Labrador to Newfoundland I came across these images.
I was a bit more apprehensive of what road conditions I'd encounter, even in September, but prepared as best I could and had a wonderful time.