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Biking in the Berkshires

By Kenzo

New England inspiration

Exploring the hills of western Massachusetts

Moby Dick is crowned by a lighthouse, not Ishmael’s harpoon, although what the great white whale and a lighthouse are doing so far from the sea are two separate stories that become one only because I’m here.

The Berkshire Region of Massachusetts lies west of the Connecticut River and extends to the New York border. Although lower in elevation, the Berkshires are the southern extension of Vermont’s Green Mountains and cutting through them from Greenfield to Williamstown is the most popular motorcycle-touring road in The Bay State: Route 2, The Mohawk Trail.

I approached from the north, riding down the twisting North River Valley to Shelburne Falls, a village rich in industrial history but that now is better known for its Bridge of Flowers, an abandoned trolley bridge that was transformed into a botanical garden in 1929.

The Mohawk Trail follows the Deerfield River west to the base of the Hoosac Range and then climbs over the mountains, where a scenic pull-off at the eastern Summit Gift Shop offers an expansive view of mountains fading into the distance. Deep beneath my feet lies the 25,031-foot long Hoosac Tunnel, the longest railway tunnel east of the Rocky Mountains and reputedly the most haunted place in New England. Twisting down the western slope and through the famous hairpin I continue my descent to the former mill town of North Adams. There are few major highways that are this much fun to ride.

Long-idle utilitarian factories are being converted into condominiums and artist studios as this staid mill town becomes transformed into a hip urban oasis that includes the Massachusetts Museum of Contemporary Art, the largest contemporary art museum in the world.

Williamstown is called “The Village Beautiful,” where gracious homes and spacious lawns bespeak of old money spread across the extensive campus of Williams College. The Sterling and Francine Clark Art Institute has a world-famous collection of work by French Impressionists, 19th century American artists, European paintings and early photographs. All this culture is tucked into the northeast corner of the state only three miles from the Vermont and New York borders.

I’ve established my base of operations on Route 7, south of Williamstown in one of the five tastefully furnished suites at the 1896 House. Dropping off my gear, I continue down the highway and turn onto Greylock Road.

The summit of Mount Greylock at 3,489 ft. is the highest point in the state and a magnet for riders touring the region. The narrow, winding roads through the state reservation are a delight despite the 25 mph speed limit. Two buildings grace the summit: the gorgeous Bascom Lodge built by the Civilian Conservation Corps during the Great Depression, and the Massachusetts War Veteran Memorial. The latter was designed for the Charles River Basin in Boston, but a bit of politics caused the 93-foot-high granite lighthouse to be erected here. The 360-degree panoramic view from the observation level of the war memorial is stupendous.

On this lofty mountain Henry David Thoreau underwent a personal transformation that led to Walden Pond, and it was here that Herman Melville met his mentor Nathaniel Hawthorne. The snow-covered mountain as seen from his home, Arrowhead, in Pittsfield, gave Melville the inspiration for his great white whale, Moby Dick. The only inspiration I receive is not literary, but to discover whether or not I can coast all the way from the summit to North Adams.

A private chef is on hand to prepare my breakfast, which doesn’t encourage getting on the road at an early hour! Somehow I manage to get rolling and a couple miles down the highway turn onto Route 43. Hancock Road follows a long, narrow valley through the Taconic Mountains and across the border into New York. Route 22 takes me south where I link up with U.S. Route 20 for a wonderful ride over the mountains on a road filled with sweeping corners that returns to Massachusetts.

The Hancock Shaker Village is located on U.S. Route 20 at the junction of Route 41. It’s one of the best-restored Shaker villages in New England. The great round barn was built in 1826, decades before the “modern” agricultural movement advocated the building of round barns for efficiency of labor. Tools are still in the original workshops, the Great House is furnished, there is livestock in the barns and the gardens are planted. The structure of their 19th century communal lifestyle was a promising social experiment; however, as someone once stated, any religion that’s against sex is going to be short lived.

Route 41 leads to Great Barrington and it’s a wonderful motorcycle road, but there’s a better one. Immediately after crossing over the railroad tracks I turn left onto Lenox Road. This brings me to Route 183 and Tanglewood, the summer home of the Boston Symphony Orchestra and site of famous music festivals. Nathanial Hawthorne and his family briefly lived on the Tanglewood estate—a replica of the “red house” is on Hawthorne Road—while writing The House of the Seven Gables.

There have been other writers, musicians and artists who have been inspired by the Berkshires. Continuing south on Route 183 to Glendale, I intend to visit the homes of two of them and a place made famous by a third.

Norman Rockwell lived in Stockbridge from 1953 until his death in 1978. The Norman Rockwell Museum has the largest and best collection of the artist’s work and his archives, but I’m more interested in his studio, a modest cottage that contains his personal effects—even his paints and brushes.

Just down the road is another artist’s home and studio, Chesterwood. Daniel Chester French is best known for his “Sitting Lincoln” in the Lincoln Memorial and the Minuteman statue in Concord, Massachusetts, but I never understood the essence of the American Renaissance until touring this national historic site.

Turning onto Division Street just north of Great Barrington I locate the Old Trinity Church. This was once the home of Alice and Ray Brock, a place that became a folk legend when one of Ray’s students at the Stockbridge School turned the story of a memorable Thanksgiving dinner into a ballad called Alice’s Restaurant Massacre and the subsequent movie. Today the church is a multi-denominational center funded by a foundation set up by Arlo Guthrie.

It’s not a pretentious town, but Great Barrington does have history to be proud of. In front of the town hall is a memorial that commemorates armed resistance against the British two years prior to the Revolutionary War. Another milestone took place in 1781 when slave Elizabeth “Mum Bett” Freeman successfully sued for her freedom in county court.

I head north on U.S. Route 7 through Stockbridge. The village is much smaller than its reputation would lead one to believe and some of its special attractions are easily overlooked. On the corner of Main and Elm water still flows in the horse trough built in 1881—although I’ve never seen anyone drinking from it—and the burial ground for the Mohican tribe is found next to the village green.

Lenox was once called the “Inland Newport” where over 75 “cottage” estates were built by the ultra-rich during the late 19th century. Some of these grand mansions, such as Bellfontaine and Elm Court, have been transformed into exclusive inns. Other estate properties have been converted for different uses: Shadowbrook is now the Kripalu Center and Highwood is Tanglewood. Edith Wharton’s estate, the Mount, is open to the public. However, my only stop is at Ventfort Hall, the mansion of George and Sarah Morgan, now the Museum of the Gilded Age that was portrayed as St. Cloud’s Orphanage in the movie The Cider House Rules.

Traffic dramatically increases as U.S. Route 20 merges with U.S. Route 7 outside of Lenox and continues to Pittsfield, the economic hub of the region. From here I have a number of highway options, but choose Route 8. Running along the valley between the Hoosac Range and Mt. Greylock the road leads north, taking me back into Vermont. There are hundreds of miles of great touring roads crisscrossing the Berkshires, but for now they just have to remain my secret.

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