This trail is a great way to get into backpacking. The trail is not super easy but it is not hard either. It is just right for getting out on a long weekend and just putting down some miles. All the lean-tos are very well taken care of and the trail is in good shape. You will however run into more traffic towards Monadnock.
Really you can get to this trail from many points. I would recommend starting on the Northern part of the trail up by Newport. This way you finish at the high point of the trail. I would recomend getting the guide book to help plan the trail and figure out how to get to it. Google will not help you here.
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