You can see how the Taconic Trail (NY 2) became somewhat longer and more curvey as it became a developed highway, to help reduce the steepness of the grade over the mountains.

The Taconic Trail (NY Route 2) winding up it's way over the Taconic Crest into Massachusetts. The south-west corner of Vermont is in the upper west corner of this image - you can add state lines to see in greater detail. I've always kind of liked that little run-down homestead up in the shadow of the mountain as you start to climb this rather rough road. Much of the wild land in his photo is either the Taconic Ridge State Forest or the lands of Williams College.