The road between Winfield and the trailhead (junction) is a bit rough, but not any worse than the bulk of the Gray‘s Peak road.
There was some ice on the road in sloped spots that made 4wd handy, but probably not necessary.
I wouldn‘t recommend driving very much past the turnoff to the actual trailhead, the road gets quite a bit rougher, and there are spots with tall rocks in tight corners, may be difficult to navigate without a spotter. Parking just up the road from the junction only adds about the 200 yards to the hike.
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