Prepare for an entire day out on the trail and a car-spot at each trailhead. This section of the AT is beautiful! The trail has some uphill and downhill climbs, passes by amazing wetlands and ponds (great stopping point for lunch), has spectacular views of the Greylock Range and ends at an exposed rock face called the Cheshire Cobbles that has great views as well.
The best way to take this trail is from the south to the north. Spot the first car in the center of Cheshire at the church and then head south on route 8 towards Pittsfield. When you reach a major intersection and lights (Friendly's will be on your right), go LEFT onto route 8/9 combined. Stay on this road for a mile or two then go left on Pleasant street and left on High Street. Follow High until it turns to a dirt road and park your car at The Boulders parking area (look for the AT sign). Head to the right up the AT heading north and ENJOY!
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