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Riding The Berkshires

March 14, 2018
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Berkshire County offers fantastic roads for the motorcyclist and a rich past for the history buff

Story by: Ron Keys
Photos by Ron Keys and Berkshire Tourism

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…

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