As I ALWAYS post - consider doing the CD Trail from South to North rather than North to South. Rain/Snow, Wet/Snowy ground, and (Less) Prevailing Winds suggest the above. Including two precip curves from Helena, MT and Grants, NM - higher elevations have even more precip - but the same general curve. What it comes down to is that it is often wet and chilly in mid June in Montana - but nice and dry by mid August. In New Mexico, June is the end of the dry season, by August the monsoon rains turn the clay roads into quagmires.
Best - J