Historic Park Square, Pittsfield marks the central point in Berkshire County where all directional roads meet: North, East, South, and West.
Follow Route 7 South from Park Square one block and turn right onto Route 20 West. This scenic roadway passes by Clapp Park. Leave the neighborhoods of Pittsfield behind and enter the rural countryside of old farming communities.
Turn left at the intersection with Route 41 and follow south along one of the prettiest Berkshire roads reflecting old New England. The town of Richmond paints a charming picture of white, clapboard homes. Route 41 South soon enters the village of West Stockbridge where its center focuses on shops and restaurants. Crossing through the center of this busy area is the Williams River. In a short distance, Route 41 intersects with Route 102 East.
Follow 102 East into Stockbridge to Route 183 North – a left turn at a yellow blinking light. This area is full of attractions, rich with history and popular with locals as well as visitors. Continue along Route 183 North into the center of Lenox. Notice the colorful Victorian Inns and attractive galleries that fill the town.
Stay on Route 183 North until it meets Route 20 East – a right turn. 20 East travels just minutes into Lee, ducking under the MA Turnpike. 20 East soon enters rural Becket. Once inside the town of Becket, look for the left turn onto Route 8 North. Winding through the hilltowns of Becket, Washington, and Hinsdale, with an off-shoot into Peru, Route 8 North eventually leads into Dalton. Stately church steeples and colonial style architecture describe this old town of the Berkshires.
Nearing the end of this tour, Route 8 North intersects with Route 9 South in the Allendale section of Pittsfield. 9 South guides drivers to the conclusion of this tour at Park Square in central Pittsfield.
If you prefer a pdf of this to take on the road with you then click here.