The section of US 287 near Depuyer is a little dicey with a large trailer. You'll be okay if you take it easy and it is scenic. However, if you're looking for the easiest way (and still fairly scenic - look out the left window the whole way and you'll be staring at the Rocky Mtn Front the whole way), I'd suggest taking I-15 to exit #348, just north of Conrad. Take MT-44 through Valier and it'll dead end at US 89. Take it the rest of the way to Browning. It's all good highway and not heavily traveled. That's the way I'd pull my trailer.
