The Berkshires Blog

Not to be Missed – Breathtaking Foliage Drives

By Lauren R. Stevens

The south end of Berkshire County is laced with highly drivable, colorful, quiet country roads. Folks coming to the area from New York, via the Taconic Parkway, will find themselves on those back roads as they enter the county. Great Barrington and its coterie of towns—Alford, Egremont, Sheffield, New Marlborough, Monterey and Tyringham—provide loops galore, most of them hooked into Routes 7, 41, 23 and 57. So it is hard to get lost if you have a general idea of where the numbered routes run—basically north and south except for 23. The colors of autumn will hit here a bit later than farther north but look for the red maples along bogs or brooks, as on Rte. 7 just north of Great Barrington or along lakes Buell and Garfield in Monterey.

This fall will be a good occasion to check on the Monterey General Store, on Rte. 23, which may have reopened. Another worthwhile stop is Rawson Brook Farm, New Marlborough Rd. in Monterey, for dairy, eggs and the specialty, Chevre (goat) cheese.

Take in the sights.Richmond, Lenox, Washington and Becket also have their foliage charms, with many brilliant sugar maples at the higher elevations. With a simplicity of road patterns: Routes 41, 7, Washington Mountain Rd. and Route 8, all you really need to know to feel comfortable exploring is that they tend north-south —with a special shout out to Rte. 20, Jacob’s Ladder Trail, a Massachusetts Scenic Byway and the address of the Jacob’s Pillow Dance Festival. Bartlett’s Orchard on Swamp Rd., in Richmond, grows and squeezes its own apples into cider, tastefully served with doughnuts.

Breathe in the fresh air.Finding your way to the scenic roads in North County can be more confusing, so let me make a specific suggestion. For a 60-mile loop, begin on Quarry Road, at its junction with the road to the Mount Greylock Visitors Center, in Lanesborough. (You might want to stop at the Visitors center to pick up “Mount Greylock’s Hidden Treasures,” a guide to the last leg of today’s trip.) You are going to view Greylock in its autumn splendor from several angles and then drive over the range.

Skip the traffic.Follow up and over Lanesborough Mountain Road (gravel and steep) to Rte. 8, then duck quickly south on Lanesborough Road, essentially following the back side of Cheshire Reservoir. Before turning left on Summer Street, stop at Lakeview Orchards for the requisite cider and doughnuts, made the natural way—without preservatives. Jog right on Partridge before bearing left on Swamp Road, grazing a corner of Berkshire Mall. Cross Route 8 by the Arizona Pizza (in case cravings are on you) to follow Gulf Road (gravel) into Dalton. Congratulations. You have now driven two of the most obscure and forested roads in the county.

Grab a bite to eat on the way.But the ride isn’t over. Follow High Street to Routes 9 and 8-A, and on up the Berkshire Trail to Windsor, where you stick with 8-A as it makes its own way north. You are now into the area where trees change early, especially the gaudy sugar maples. Follow left on Route 116 in Savoy, then down off the Berkshire Plateau to a right on Stewart White Road. Your road becomes East Road in Adams, with startlingly dramatic views of Greylock—and the Specialty Minerals limestone quarry. Drive into North Adams on Church Street and left on another Scenic Byway, Route 2, the Mohawk Trail, west to Notch Road to the Mount Greylock Scenic Byway. Greylock and its subsidiary peaks are the highest in southern New England. Numerous pullovers provide leafy views on the ways up and down. Ascend all the way to the summit. Take a stroll around. The tower may be open for the ultimate long-range view. Or look east, directly down on the town of Adams. Stop by Bascom Lodge for hikers’ breakfasts, snack bar lunches and superb dinners (reservations required).

Descend (using low gear to save your brakes) until you come out where you began, having had an adventurous as well as a scenic experience.

Learn more about Berkshire scenic driving tours >>

A newspaper columnist, reporter and magazine writer, Lauren Stevens is the author of several books, including the enlarged 3rd edition of his Hikes and Walks in the Berkshire Hills and the 8th edition of The Berkshire Book. Stevens is also an environmental columnist for The Berkshire Eagle and an environmental planning consultant. He founded the Hoosic River Watershed Association in 1986 and has served on the board continually and as president several times since. Stevens taught English and environmental studies and served as Dean of Freshman at Williams College.