For a nice early winter, or late winter day, try this. Watch for ICY
spots, especially in the shadows. So head out early, down to Monument,(the back way) for coffee. Then get through the Springs anyway you can.
The tak the short cut to Penrose,(I think it's hwy 15). On to Canon city. Then pick your choice back, Phantom canyon or Shelf Road. The back to Woodland park. Lots of options depending on time, weather etc. Then either Rampart Range rd, or through Deckers home. Again, it's should be a nicer warmer day when you do this. But I have done it in January. Mostly highway, but some dirt. OR
It can be wonderful exploring the Plains on nice winter days. We went to The Sand creek Massacre site right after Thanksgiving. great ride, much can be done on gravel. Check ou the maps and info on Fort Tours.com.
If you are a history buff, there are some great places to see on the Plains. Like Picketwire canyon, or Apishipa canyon. The Canyon Land of Colorado are Beautiful
And doable on nice winter days. but as soon as the sun starts to hit the horizon it gets cold fast, and water starts to freeze on the highways.