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SCENIC DRIVING TOUR 1: Northern/Central Berkshire – Approx 64 miles

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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SCENIC DRIVING TOUR 2: Central Berkshire - Approx 78 miles

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.

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SCENIC DRIVING TOUR 3: Southern Berkshire - Approx 48 miles

Beginning in the southern most town of the Berkshires, Sheffield, settled in 1725, Sheffield is the oldest Berkshire County town and has become a mecca of antiques shops. Follow Route 7 North through Sheffield to the town of Great Barrington. Close to the CT border and two hours from NYC, Great Barrington has become transformed into a fast growing town with colorful shops and restaurants. Venture off of Route 7 in the center of Great Barrington turning West onto Route 23 in the direction of South Egremont. Here local inns pride themselves by offering home-cooked breakfasts to their overnight guests. Look for the intersection of Routes 23 and 41 South. Follow the signs for Mount Everett State Reservation and Bash Bish Falls. A walking trail leads to the cascading music of nature and vistas of the falls. Return to Route 41 South also called Berkshire School Road. This leads back to Route 7 in Sheffield. A right turn onto 7 South leads to the village of Ashley Falls, another area known for its historic preservation and nature trails. Cross Route 7A in Ashley Falls and take the first right, cross Route 7 and continue to Clayton. Once in Clayton, turn left, following the Konkapot River Valley to Mill River, an old New England farming village. From Mill River, follow the winding road north past Lake Buel until it intersects with Route 23, on the eastern side of Great Barrington. Turn left onto 23 West to Great Barrington’s center and then follow Route 7 South back to Sheffield.