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Appalachian trail
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Appalachian Trail is a very long trail (goes through several states) that goes through this area. It is a nice trail to visit.
Parts of the Appalachian trail in Massachusetts are accessible from Monterey, West Stockbridge, Rte. 7 in Stockbridge (connecting trail) Rte. 20 in Lee. If you're through-hiking, none of the trail heads are really close to the towns, but if you're day hiking, all of the trail heads have good parking.
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