Begin at historic Park Square in the center of Pittsfield on Route 7, just a block north from where Route 20 bears off westbound towards New York.
Driving north from here on Route 7, pass by the beautiful mountain panorama surrounding Pontoosuc Lake. There are several beaches open to the public as well as rentals for sail boats, jet skis, and canoes.
Once in Lanesboro, turn right onto Berkshire Mall Road and follow to its connection with Route 8 North. 8 North winds through the town of Cheshire before it arrives in Adams. A favorite pastime for locals and visitors is to bicycle on along the Ashuwillticook Rail Trail which runs parallel with Route 8. The Trail offers great scenic vistas of lake and mountains and places to stop for refreshments.
Approaching the center of Adams, turn right onto Route 116 East, leaving behind this charming town while entering the rural beauty of the area’s farmlands and forests. Route 116 winds upward in elevation.
After entering Savoy, look for River Road on the right leading to the Windsor Jambs, Windsor State Forest. This is a popular area for hiking and camping and is operated by the Department of Environmental Management. River Road passes by a cascading waterfall of spring water at the “jambs” next to Windsor Pond.
Upon leaving the forest, River Road will meet Route 9 in Windsor; turn right onto 9 South. Follow through the old towns of Windsor and Dalton before returning to Pittsfield, via the busy Allendale Center and back to historic Park Square.
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