Riding The Berkshires

Story by Ron Keys// Photos by Ron Keys and Berkshire Tourism
March 14 2018

Berkshire County offers fantastic roads for the motorcyclist and a rich past for the history buff

The Massachusett people, meaning “by the range of hills,” roamed these valleys, flanked by pitching mountains bursting with green and pristine streams brimming with fish for centuries. Then, in 1620, fleeing religious persecution, the Pilgrims arrived, and with them European diseases. With no immunity, 90 per cent of the Massachusett people died. In 1629, after some Anglicization, Massachusetts became the name of America’s second English colony.

As Europeans continued their migration westward, beautiful Berkshire County became the namesake of the shire in 1761, with the same moniker in England. The Berkshires, part of the Appalachians, run north to south through the county, and along with hundreds of kilometres of twisty motorcycle roads, 145 km of the famous Appalachian Trail also course through its beauty.

Into the Hills

Hancock Shaker Village Round BarnIt’s a windless, warm morning as Tony Fletcher – a friend from my old Yamaha racing days – and I leave the Harbour House B&B in Cheshire. Winding north through the green hills, we cautiously ride by the Massachusetts State Police Station on our way to Adams, then over to MA 116 on our way to Savoy. With no traffic, we languidly enjoy the sweeping curves. Savoy – a hamlet of a dozen homes, a store and a white, steepled church with peeling paint – is soon in our mirrors and the stone hedgerows blur by, a memorial to the blood, sweat and tears of the pioneers who cleared these wooded fields. Massachusetts 8A courses us through a lush valley along King Brook and then Chickley River to Hawley, a unique settlement of old trailers. I am sure I hear “Dueling Banjos” playing as we pass by. The tree-enveloped twisting blacktop demands our attention, and just over the bridge at Deerfield River we arrive at MA 2, the Mohawk Trail, a western Massachusetts scenic byway. We are surrounded by mountains, gleaming in varying hues of green, and I shout to Tony, “The A in 8A must stand for ‘Amazing!’”

The 104 km-long Mohawk Trail was for centuries a pathway used by native peoples, and today it has been designated as one of America’s scenic byways, following the same route alongside Miller River, Deerfield River and over Hoosac Mountain. Zoar Road careens alongside the Deerfield River and the railroad tracks, and then winds upward toward Hoosac Mountain. A bit lost, we meet two men in a pickup truck who are railroad workers, and they lead us the rest of the way to the tunnel. There will be no train this morning, because somewhere inside that 8 km of eerie darkness, repairs are underway. As we approach the eastern portal, a rush of cold air greets us: a west wind blowing through the tunnel is cooled to Mother Earth’s constant temperature of 14 C, and provides a welcome moment of relief for us.

Ghostly Sightings

house-in-berkshire-countyIn 1851, Hoosac Mountain was a formidable barrier preventing the movement of goods east and west. The tunnel was an 8 km-long battle between man and rock. The conflict lasted for 23 years and cost more than 200 lives. Black powder was initially used, and later nitroglycerine was invented. Its unpredictability took many lives. Most of the casualties were from explosions inside what was dubbed “the Bloody Pit.” Since those days, aberrations, strange lights and ghostly figures have been seen in and around the tunnel.

Backtracking to Whitcomb Hill Road, about 5 km of newly paved, peg-scraping delight scale us upward to the Mohawk Trail. At “the Hairpin,” the Golden Eagle restaurant sits on a cliff overlooking the Hoosac Valley, and farther down, entering North Adams, we stop at Gus’ Barber Shop, where I am fourth in line behind three bald-headed golden-agers. Gus, who is in his 80s, tells me why he still works: “I love my wife, but being with her 24 hours a day – not good,” he says with a chuckle.

It’s a bit ironic that with my grey locks lying on Gus’ floor, nearby Mount Greylock beckons us. So, after lunch at the Freight Yard Pub, we meander along the narrow Notch Road, 13 km upward through deciduous and boreal forest. At 1,064 metres of elevation, Mount Greylock is the highest point in Massachusetts, and we can see Vermont, Connecticut, New York and New Hampshire from its peak. The imposing Veterans War Memorial Tower stands 28 metres above the summit, honouring men and women from all wars. Mount Greylock became the state’s first wilderness park in 1898.

Great American Pastime

riding-across-berkshire-countyWith the Beamers’ exhaust reverberating against the mountainside, we thread downward through the lush maples and oaks of Greylock’s southern spine. At Lanesborough, we tool along Old Cheshire Road, flanked on the left by stone fences separating green pastures and on the right, the pristine Cheshire Reservoir. Rolling past white clapboard farmhouses with cupola-capped ochre-red barns, it is a scene revealing the harmonious blend of humans and nature.

Later that evening, we sit with the locals, enjoying an intercollegiate baseball game, chomping on burgers and watching the North Adams SteepleCats lose again to the Valley Blue Sox. The name “SteepleCats” appropriately came from the number of church steeples in North Adams. Ascribed as the “Great American Pastime,” the first record of baseball in the U.S.A. was a 1791 Pittsfield ordinance: “Citizens are not allowed to play ball close to buildings with glass windows.” Glass was an expensive luxury in 1791.

After another magnificent Harbour House breakfast, we mosey along MA 116, only this time we turn right onto MA 8A before Savoy and head south toward Windsor. Low forests and verdant pastures blur by, and with few homes and fewer cars, the route and the morning are perfect.

Memories Flood Back

At Windsor, we take a right toward Dalton, the home of the 1973 International Six Days Trial (ISDT) and many personal memories. Once upon a time, I spent six days of torturous riding, testing my machine and me. I now treasure the silver medal I won, my one and only attempt at the Olympics of motorcycling.

Cruising alongside the Housatonic River, MA 8 meanders into Hinsdale. Originally named Partridgeville in 1771, it was later renamed Hinsdale, after Reverend Theodore Hinsdale, who also owned the town mill on the Housatonic. Outside of town, a bright yellow sign in my peripheral vision says, “LOOK for Motorcycles,” with the two o’s being eyeballs. I think to myself, how clever. The tall June grass on the roadside sways in the breeze as Tony blasts by, and the green, leafy trees, like a bower over our heads, give us some shade as we hustle through the boundless curves.
In Becket, with a stone retaining wall on our right, Yokum Creek burbles its way through town, as do we. Becket Road construction crews wave us by on our way to County Road, where a right and then a quick left sets us on our way to Lee. County Road becomes Yokum Road then Becket Road, and is a plethora of curves carved through the lush forest. Turning onto MA 20, I hit the brakes and pull over. There sits a 2.5-metre-tall beaver on a wagon. It’s called Beaver Storage, and I chuckle and ask Tony if this might be Hugh Hefner’s summer place.

Skirting around October Mountain, this mass of rock and bush presented an insurmountable obstacle for some competitors in the 1973 ISDT, but today we are on a less arduous path. Lee was originally the territory of the Mahican Indians and was called Dodgetown for many years, but after the Revolutionary War, it was named Lee, after General Charles Lee. Like so many towns in the Berkshires, Lee was also a mill town unlike Lenox, which was better known as a place for summer homes of the country’s elite.

A Well-To-Do Town

It is obvious from its beautiful homes that Lenox was home to the affluent and well moneyed of the Gilded Age. Here, people like the Morgans, Nathaniel Hawthorne, George Westinghouse and the Vanderbilts lived at various times. Lenoxites of our generation would be James Taylor, Maureen Stapleton and Yo-Yo Ma. Lenox is also the home of Tanglewood, the summer residence of the Boston Symphony Orchestra and the Tanglewood Music Center. Frequent performers here include James Taylor, John Williams and the Boston Pops.

Leaving Lenox, we follow the curves winding upward through the maple forest on Richmond Mountain en route to historical Hancock Shaker Village. Destined for extinction because of their creed – complete celibacy – the Shaking Quakers, known as the Shakers, believed: “Hearts to God and Hands to Work.” The two last Shakers left in the world live at Sabbathday Lake Shaker Village in Maine. The Hancock Shaker Village displays what it would be like to live this Puritan lifestyle, and the innovative designs they came up with are still copied today. Shaker pegs, furniture and boxes are just a few of the simple, functional and durable legacies they gave us. Tony and I sit with rapt attention as a guide takes wood from a steam box and bends it around a form, making a genuine Shaker box before our eyes.

Whale of a Story

After lunch, we mount up in the heat and head across South Mountain Road to Holmes Road on our way to Pittsfield. Although he started his book in New York City, Herman Melville moved his family to Arrowhead and there completed his literary classic, Moby-Dick; or the Whale. From his studio on the second floor of his home, called Arrowhead, he had a clear view of Mount Greylock, which in winter can resemble a large whale. Melville, a very successful author at age 25, first released The Whale; or Moby Dick in Britain, where it was a huge failure. He then released it one month later in America, where it again flopped. He lost a fortune trying to promote the book and later moved back to New York, where he worked as a customs inspector until his death in 1885. It was not until some 40 years after his death that his epic novel became a masterpiece. And again, with refreshments in hand, Tony and I relax in our rocking chairs at the Harbour House Inn, quietly contemplating just a small sampling of the treasure trove of history that Berkshire County holds. Tomorrow, we know, will be a different sampling entirely.

A Collector and Restorer

Just east of Adams, Henry Wood Road take us up the hill to the home of Jim Hoellerich, one of New England’s most trophied riders and one of the primary organizers of the 1973 ISDT. Hoellerich is not only a great rider, he is also a well-known collector of Spanish motorcycles, namely Ossa and Bultaco, which, along with Montessa, were ranked among the best choices for motocross and enduro riding in the sports’ golden years. Although these marques are extinct today, he has professionally refurbished a phenomenal collection that is on display in his museum on his 400-acre farm. Hoellerich proudly takes us on a two-hour tour of his motorcycles and the paraphernalia he has collected over the decades. Even well-known politician John Kerry, an avid motorcyclist, has made the trek to Cheshire, to see Hoellerich’s collection and a who’s who of dirtbike racers of the era. After the tour, Hoellerich suits up and throws his 83-year-old leg over his Ninja 300 to show us some back roads. I try to keep track of where we are but lose all sense of direction, and suddenly we are stopping just outside of Dalton. Hoellerich points across a field where a couple of Holsteins are grazing to where the ISDE Parc Fermé and the start/finish line was. I stand quietly and close my eyes, peering through the mists of time, envisioning how it looked on that cool September morning 44 years ago. A very special moment for me. Thank you, Jim. After a few more kilometres of his favourite roads, we bid farewell to him and hike it over to Stockbridge for a tour of the Red Lion Inn and dinner in Widow Bingham’s Tavern.

This was where our Canadian Yamaha Team stayed in 1973, and it looks much the same today – except now, it is a four-star hotel. What a great day, chock-full of personal nostalgia. Alice’s Restaurant However, a trip to Berkshire County would not be complete without a visit to one of its most celebrated citizens: Arlo Guthrie. Those of us who are mature enough can probably remember the tune “Alice’s Restaurant Massacree.” Back in the autumn of 1965 in Great Barrington, Massachusetts, Guthrie and his friend Richard Robbins thought they would help Alice and Ray Brock by taking some of the Brocks’ renovation garbage to the dump on the morning after Thanksgiving. The dump was closed, so they chucked the garbage in a ravine. Guthrie and his friend were arrested for littering, and the story is memorialized in the song, which was also an anti-Vietnam War statement. Alice didn’t actually live in the restaurant; she and her husband actually lived in a church nearby.

In 1991, Guthrie bought the old Trinity Church in Great Barrington where Alice and Ray lived and thus began the Guthrie Center in honour of his parents, Woody and Marjorie. It’s an interfaith church and is used for meeting other needs of the community. Evenings have musicians of all stripes dropping in to jam, and this evening finds Tony and me listening to four different musicians who have come in for the Thursday night Hootenanny. I will never forget Peter Lehndorff, a talented songwriter and musician, as he gave his personal account in song of how he lost his father, his uncle, cousins and finally his wife to the dreaded Huntington’s disease. There was not a dry eye in the house when he finished. If I knew then, what I know now I couldn’t change much of anything, anyhow. It was 50/50. Life’s a coin toss. When you have to dance the Huntington’s Waltz. Peter Lehndorff On this melancholy note, Tony and I have spent our final evening in Berkshire County. But the positive spin of Lehndorff’s song is to live life to the fullest. And with a sense of completeness, our Berkshire County adventure has drawn to a close.


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