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Ashuwillticook Rail Trail Cheshire Segment
Easy paved rail-trail segment with mountain and lake views.
Make a Day Trip
Estimated total time: Varies
Wahconah Falls Trail
Short out-and-back to a prominent Berkshire waterfall.
Mount Greylock Summit Trail
Classic Berkshire climb to the highest summit in Massachusetts.
Money Brook Falls Trail MA
Steeper woodland route to secluded cascades in northern Berkshire terrain.
About This Trail
An easy paved rail-trail segment through the scenic Hoosac Valley between Cheshire Reservoir and the Berkshire hills. The flat route offers views of Mount Greylock and passes wetlands, farmland, and the shore of Cheshire Lake on a smooth, accessible surface.
Getting There
Nearby Trails
Wahconah Falls Trail
Short out-and-back to a prominent Berkshire waterfall.
Mount Greylock Summit Trail
Classic Berkshire climb to the highest summit in Massachusetts.
Money Brook Falls Trail MA
Steeper woodland route to secluded cascades in northern Berkshire terrain.
Natural Bridge State Park Trail MA
Short walk through marble gorge formations and riverside scenery.
Tannery Falls Trail Savoy
Forest hike to multi-tier falls in Savoy Mountain State Forest.
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