Winter Road is a short connector that bypasses a nasty wall on Green Mountain Road. The problem with the steep climb is that a motor vehicle could come ripping up beside you on the narrow road as another one launches off the lip of the drop above you. That could get all kinds of ugly. So it's a great excuse to take a gentler grade beside a small stream in an attractive little ravine.
Coming the other way, I just launch off the drop. The trees are sparse enough for me to scope out the intersection with Winter Road at the bottom. I can also get a view down the road to see if anyone is coming who might turn in front of me. It's actually safer than trying to make the left turn onto Winter Road when someone might come barreling down Highwatch Road as you're trying to make a tight left over the ever-present patch of sand.