See pretty forests, lakes, mountains, and charming towns of New England, giant cheese, beautiful gorge, birds, an aquarium, and a lovely waterfall.
On the western side of Massachusetts, bordering New York, is a region known as the Berkshires. It’s actually a county comprising some of the prettiest lakes, forests, mountains and towns in New England. This trip will take you through the central Berkshires, an area filled with lush forests on top of quaint New England towns.
The exciting tour begins and ends in Pittsfield. Don’t let the name trick 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 major roads. This natural-history and art museum also has an aquarium. The Berkshire Artisans Gallery in the
Lichtenstein Center for the Arts features the accomplishment of local artists, and Wahconah Park is home of the Class A Pittsfield Mets; summer visitors may be fortunate enough to catch a baseball game. Follow Route Seven north past Lanesborough and pick up Route Eight north to Cheshire. You won’t need to look very carefully for Cheshire’s claim to fame, a life-size duplicate of the 1,235-pound cheese local farmers offered to Thomas Jefferson in 1801. In the nearby town of Adams, visit the Old Quaker Meeting House, constructed in 1781 and now a memorial to the Society of Friends, who settled here in the early 19th Century. Next, take Route 116 east to Windsor State Forest and River Road, where you’ll find Windsor Jambs, a gorge formed over the centuries by a brook–one of the most picturesque parts of the Berkshires. Pick up Route 112 south to poet William Cullen Bryant’s farmhouse just outside Cummington. The carefully preserved spot highlights furnishings dating from the 18th Century.
Next, take Route Nine toward Windsor, past the Notchview Reservation, a 3,000-acre preserve with 15 miles of trails and plenty of opportunities for cross-country skiing and bird-watching. While you’re there, don’t fail to see Wahconah Falls, a beautiful waterfall at the foot of the Berkshire Trail. Continue on Route Nine to Dalton, home of Crane Paper Co.; visit its museum to discover about the history of papermaking in America. Continue on Route Nine to reach the end of the trip back in Pittsfield.
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:
Wahconah Falls
Windsor Jambs
Notchview Reservation
Tagged with: best time:Fall • forest • Massachusetts
Filed under: Best Road Trips