If going up I25 you go over Raton Pass first and then once you are in CO and going to Pueblo CO then heading over to Durango CO you have Wolf Creek Pass.
Wolf Creek PassWolf Creek Pass can be one nasty pass. Steep on both sides.
One thing to remember if driving a newer diesel truck with an exhaust brake and traveling on ice you don't want to use your brake if going down hills. It could cause your rig to jackknife. So all the way down the passes you will be using you truck and trailer brakes. Also make darn sure your trailer brakes are set up properly. You won't want them to put to much force and cause the trailer tires to slide and yet you want them enough to make sure that all of the braking is not done by the truck because that would be just like using the exhaust brake. It is a fine balancing act between truck and trailer brakes.
I lived in CO for 27 years and before that I was born and raised in NW Montana so I was very used to snow and ice and pulled 5ers for over 40 years off and on. If is was me I
WOULD NOT pull my 32' 5er over these passes in the winter time.
How much winter driving experience do you have. Are you comfortable driving on snow and ice roads with just your truck for hours on end? If not then sure don't try it with your truck and trailer.
If you decide on it make sure you have chains for both the truck and trailer and know how to install them because if you need to put them on it is not going to be in a nice warm weather, it will most likely be snowing, blowing and cold.
This is IMO
