Originally Posted by
TRRed
To add a word of caution to the above suggestion, Hwy 285 has a pass or two that can have some black ice in winter weather. I haven't driven it a lot so my knowledge is isolated to a few situations that I have either first or second hand knowledge. Be smart about whatever vehicle you rent and be willing to pull off the road for a while and wait for a sand truck to pass if conditions are poor.
Certainly a good suggestion. Driving it every weekend or so, I'd throw out that the only times I've had an issue are when it's extremely windy, the road between Fairplay and Jefferson (and up to Kenosha pass) can turn into a slip and slide. But absolutely worth keeping in mind if there's been recent snow or a melt/freeze.