The weather is definitely getting a lot colder as winter approaches, but for many, the snow has held off and the roads are still clean and dry.
As long as the roadways in your area haven't been salted or sanded, you're good to go when it comes to winter rollerblading!
The key for comfort during the colder months is dressing in layers, with a windbreaker shell, much like you would while hiking. The reason for this is that you will block the cold winds, while at the same time being able to peel some of those layers off when you heat up.
Another good idea is to wear a bright orange winter hat, so as to keep your ears from freezing off and also to be more visible to hunters and motorists. Bears and deer don't rollerblade, but some hunters will shoot at anything that moves and isn't flourescent orange, so be careful.
Lastly, and perhaps most controversially, I would recommend wearing a pair of ski goggles while winter blading. The conditions are very similar to those you'd find while snowboarding or skiing, and you don't wanna be blinded by the cold winds blasting your eyes. You might look ridiculous, but you're gonna have a great time doing it!