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On the western edge of Massachusetts, bordering New York, is a region known as the Berkshires. It's actually a county comprising some of the prettiest forests, lakes, mountains and towns in New England. This drive will take you through the central Berkshires, an area filled with lush forests as well as quaint New England towns.
Your classic car road trip begins and ends in Pittsfield. Don't let the name fool you: it's a quintessential idyllic New England town. Before you start your drive, stop at the Berkshire Museum just off Park Square, the hub of Pittsfield's main roads. This art and natural-history museum also has an aquarium. The Berkshire Artisans Gallery in the Lichtenstein Center for the Arts features the work of local artists, and Wahconah Park is home of the Class A Pittsfield Mets; summer visitors may be lucky enough to catch a baseball game. Follow Rte. 7 north past Lanesborough and pick up Rte. 8 north to Cheshire. You won't need to look very carefully for Cheshire's claim to fame, a life-size replica of the 1,235-pound cheese local farmers presented to Thomas Jefferson in 1801. In the nearby town of Adams, visit the Old Quaker Meeting House, built in 1781 and now a memorial to the Society of Friends, who settled here in the early 19th Century. Next, take Rte. 116 east to River Road and Windsor State Forest, where you'll find Windsor Jambs, a gorge formed over the centuries by a brook - one of the most scenic parts of the Berkshires. Pick up Rte. 112 south to poet William Cullen Bryant's homestead just outside Cummington. The carefully preserved site features furnishings dating from the 18th Century.
Next, take Rte. 9 toward Windsor, past the Notchview Reservation, a 3,000-acre preserve with 15 miles of trails and plenty of opportunities for bird-watching and cross-country skiing. While you're there, don't miss Wahconah Falls, a beautiful waterfall at the foot of the Berkshire Trail. Continue on Rte. 9 to Dalton, home of Crane Paper Co.; visit its museum to learn about the history of papermaking in America. Continue on Rte. 9 to reach the end of the trip back in Pittsfield.
Classic Car Road Trip Stats
Starting Point:
Pittsfield, MA
Distance of Drive:
68 miles
Must Eat:
South Mountain Grille
1015 South Street
Pittsfield, MA 01201
Phone: 413-499-2075
Call ahead to confirm hours of operation.
Best Time of Year for Drive:
Early spring to late fall
Points of Interest on Drive:
Notchview Reservation
Wahconah Falls
Windsor Jambs
See also:
This Classic Car Road Trip was provided by
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