Scenic Driving Tour: Southern Berkshire

Approx 48 miles

One of the best ways to view our memorable fall foliage is to take a leisurely drive. Here is a drive suggestion that will allow to discover some back rounds in the southern part of Berkshire County. Enjoy and be sure to stop along the way and snap some photos.

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 antique’s 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.

If you prefer a pdf of this to take on the road with you then click here.