I suggest to do this loop counter-clockwise, as there's a moderate rock scramble and a series of steep rock slabs (about 4 miles in) which are going to be much easier climbing up than down (especially if it's wet or icy). I also find it more gratifying to get the nice views of the distant Catskills on top of Cobble Mountain as a reward at the end, instead of the beginning of the hike.
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