Scenic Day Trip #3 - South Berkshires
South Berkshires Approx. 48 miles
Explore the countryside that inspired the likes of great thinkers like Thoreau and Emerson.
A driving tour takes you on meandering roads through hills carpeted in lush greenery, past fields
dotted with blooming flowers and under canopies of stately, towering oaks and maples into the
heart of the Berkshires' summer splendor. This particular driving tour, which spans approximately
48 miles of verdant countryside, begins in the center of Sheffield. The first town settled in
Berkshire County (1725), it opened the gates to settlement of the Housatonic Valley north to
Pittsfield. The dignified Old Parish Church in the center of town stands on the site of the first
meeting house, which was erected in 1735, and is a sterling example of New England church
architecture. Wonderful antique shops that feature authentic New England collectibles and rare
merchandise from all over the world line Rt. 7 through Sheffield. From this point, take Route 7
north to Great Barrington.
You'll come upon picturesque St. James Episcopal Church on Main Street in Great Barrington.
Throughout July and August, stop by to hear the strains of the lute and other antiquated
instruments as the Aston Magna Festival presents five concerts of 17th and 18th century music
performed on pe-riod instruments.
Retracing Route 7 for a short distance south, take a right hand turn onto Route 23 about half a
mile to the Newsboy Statue. This anonymous newsboy figure has maintained his vigil in the
small park for over 90 years. No one has been able to discover the name of the boy, but his
life-like image has captured the imagination and hearts of people the world over. The statue
was created by sculptor David Richards and presented to the town of Great Barrington in
1895 as a tribute to hard-working newspaper carriers everywhere. After paying homage to
this icon of the Protestant work ethic, continue on Route 23 to South Egremont, a quaint
municipality that was incorporated in 1731.
South Egremont was named in honor of Charles Windham, Earl of Egremont, a liberal and
friend of the American cause in the Revolution. South Egremont is also well known for its
For an optional but rewarding side trip on this Circle Tour retrace your path along Route 23.
Tucked in the fork of Routes 41 and 23 at the western edge of town is Smiley's Pond. At the
south end of Smiley's Pond, turn right at the Mount Everett-Bash Bish Falls signs and follow the
road west to the foot of the mountain. Follow Bash Bish Falls signs to the second parking area
on the western slope of the mountain where a foot path leads to the falls. Flowing through a
gorge cut 400 feet deep in solid rock, Bash Bish Brook plunges 50 feet into a deep clear rock
bottom pool to form the falls. If the light is right, you may be able to see the "Spirit Profile" of the
Native American maiden who, destitute in love, jumped to her death from the cliff above. The
falling water over the rocks still calls her name: Bash Bish, Bash Bish.
Retracing the road back up the mountain, follow the Mount Everest Reservation sign, turn left at
the Union Church in the village of Mount Washington, and right at the Mount Everett Reservation
sign, past Guilder Pond on the left, one of the highest lakes in the state, and up the mountain. A
magnificent view of western Massachusetts' rolling green expanse is afforded from the peak at
After coming back down the mountain, turn right at the Mount Everett Reservation sign and
follow the South Egremont signs back to Smiley's Pond and take a right on Route 41. On the
right is the entrance to the Berkshire School, summer home of the Berkshire Choral Festival,
whose concerts feature a chorus of over 100 voices pre-sented during July and August.
Continue south on the Berkshire School Road toward Sheffield. Back on Route 7 in Sheffield,
turn right and head south approximately three miles, then take Route 7A to Ashley Falls, a quaint
village in the township of Sheffield.
A right in the center of the village leads across the Housatonic River to Bartholomew's Cobble,
a jagged limestone out-cropping overlooking the rushing waters of the river. This National
Natural Landmark is renowned for its profuse ferns and wildflowers. Just beyond the Cobble is
one of the oldest and best preserved examples of early colonial homes in Berkshire County.
The Colonel Ashley House, built in 1735 for Colonel John Ashley, one of the town's first citizens,
was the site of the Sheffield Declaration of 1773. Now a museum, the residence is furnished
with 18th- and 19th-century antiques, including an impressive collection of Red Ware and early
industrial tools. This historic landmark, a property of the Trustees of Reservations, is open
Memorial Day to Columbus Day and offers guided tours. A small admission fee is charged.
Return to Ashley Falls, cross Route 7A and take the first right, cross Route 7 and continue to
Clayton, the southernmost set-tlement in the county. Taking a left in Clayton, follow the Konkapot
River Valley to Mill River. From Mill River north to Great Barrington, the winding road passes
Lake Buel. The Mill River Road joins Route 23 at the end of the East Mountain State Forest in
Great Barrington. Turn left on Route 23 and then left again on Route 7 for the return of the
Circle Tour to Sheffield.
Editor's note: For more information on this and eight other day trips,
pick up a copy of "Touring the Berkshires and the Mohawk Trail," available at the Berkshires
Visitors Bureau, Berkshire Common, Plaza Level, Pittsfield, (413) 443-9186. Or write to The
Mohawk Trail Association, P.O. Box 2031, Charlemont, MA 01339 or call (413) 664-6256.