Depending on the weather US285 can be very windy as you drive across South Park - which is basically south/southwest of Kenosha Pass until you head down into Johnson Village. That part of the highway is flat for the most part and very exposed to high winds coming off the mountains to the west - so if you are worried about drop offs they are very few and small. But if you are worried about towing something and getting hit by the wind - then yes it is something to pay attention to on the weather report. There are other stretches of the highway that make some climbs and a few are without guard rails but the shoulder for the most part is very generous along 285 and the drops are minor in my opinion.
It is the best way to get there - only other choice I suppose is US24 out of Colorado Springs to where it meets 285 in South Park - it is roughly the same situation - and I-25 down to CoSprings can have high winds at certain times of the year.
I am thinking that Traveler1007251 meant winding roads rather than windy? It is not a scary drive at all. I do it often pulling a camper! Just be sure to move to the right lane if you are going slow to give folks a chance to pass. It is a really pretty drive.