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A nice woods hike on the AT through Mass is the section through the East Mountain State Forest in Sheffield and Great Barrington, Mass. You can begin where the AT crosses Lake Beuel road in Great Barrington and leave a drop car where the trail crosses Brush Hill Road in Sheffield. It's a nice woods hike and I prefer it after the leaves are gone as it affords a few more views then. About 30 min from lake Buel rd. is the Tom Rogers shelter. It also includes a tent platform situated on a rock with a spectacular view looking out over the Berkshire Mtns. A truly lovely scene to wake up to. It's not a strenuous hike and would make a great overnighter to take young kids on. At the end as you come to the top of the mountain before you descend to Brush Hill Rd you have several great places to stop and take in the view over Sheffield and Great Barrington, south into Connecticut and West into the Taconic Mtns in New York. The whole trip will take around 3 hours.
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