Not all the Appalachian Trail is optimized for its own sake, some of it is for transport. In this area, the trail used to go up the Grand Staircase, down the spur labeled Pine Ledge on the topo, then through more of the Schaghticoke reservation lower down the hill than the current trail. See the historic topo, or the route at http://www.gmap-pedometer.com/?r=6990593
. I strongly suspect the view must have been much better from Pine Ledge, but with the need to avoid the Schaghticoke reservation more, that would be too much of a dead end.
North of CT-341, the AT used to go straight up the ridge from Kent School, along the western edge of the Pond Mtn map, onto Macedonia Brook Rd, a loop around Macedonia Brook State Park, back down the north edge of Pond Mtn, and rejoining the current trail on top of Caleb's Peak east of Skiff Mtn Rd. (It then used to follow what is mostly now the Mohawk Trail east from Cornwall Bridge, and again rejoin the current trail in Falls Village.)
The access through the western edge of Pond Mtn to Macedonia Brook Rd was lost after landowner permission was revoked around 1980, so the bit in Macedonia SP was removed in favor of the present route to cut off two road walks (one down CT-341 and Macedonia Brook Rd, one down what is now Appalachian Rd and was once Appalachian Trail Rd and then down Fuller Mtn Rd). I intend to see if the old route, at least through the southern tip of Macedonia, is still possible to follow, next year some time.