Taking a drive is not always about a highway or high speed run, but more concerning the scenery and winding roads.
The Berkshires region of western Massachusetts is known for its outdoor adventures like hiking and water sports, as well as cultural experiences. Home to several performance centers, including Tanglewood and Jacob’s Pillow, the Berkshires offers a variety of shows and events year-round. What’s more, there are also a plethora of museums that reel in history buffs and art lovers, including the Norman Rockwell Museum and “Moby Dick” author Herman Melville’s Arrowhead Home.
Western Massachusetts provides that opportunity along Route 7 from the southern boarder of Connecticut all the way to Vermont with plenty of side roads to explore. Route 7 provides a north/south drive from I95 in Connecticut all the way to the Canadian boarder heading to Montreal which is a popular drive for the motorcycle cruisers.
The Berkshires, throughout the seasons, presents an amazing world of contrasts for the classic car owner. Sophisticated pastimes blend harmoniously with pastoral scenery. High adventure is available with the plentitude of outdoor recreation opportunities, while a richness of history complements the area’s contemporary enlightenment.
Positioned in the rolling hills between two of the America’s best cities – New York and Boston – the Berkshires area plays out the best of two worlds. It will satisfy your yearning for the quiet, scenic countryside, yet also provide a treasure of culture, art, scenery, and hiking.
Charming lodgings, fine restaurants, excellent shopping, and an endless events calendar make every stay here unforgettable for the vintage car cruise.
This historic region offers a wealth of memorable events and activities framed by breathtaking natural beauty. The Berkshires feature year-round culture, recreation, and adventure in quaint towns like Stockbridge, Lenox, and Williamstown, while North Adams has the fabulous Museum of Contemporary Art. There is no shortage of places to stay , shop, and dine. Great ziplines and canopy tours are here; for all-day fun, visit Look Park with a zoo, lake, water spray park, 18 holes of miniature golf and six tennis courts. In winter, family-friendly skiing and other snow sports are just a short walk uphill.
Just a few of the things to do:
The Berkshire Mountains of western Massachusetts are considered one of the premier leaf peeping destinations in the United States. Every October, the trees put on a dazzling display of fall foliage to the delight of camera-wielding tourists like me. But what else is there to do in the Berkshires besides look at the leaves? Plenty! The area has long been a bastion for artists like Edith Wharton and Norman Rockwell, who found inspiration in the charmingly small town of Stockbridge. Read on to discover the some of the best attractions in western Massachusetts.
THE MOUNT, EDITH WHARTON’S HOME
Edith Wharton was an accomplished American writer and the first woman to receive the Pulitzer Prize for Literature. She was a prolific author, penning 40 books in 40 years, including her two most famous novels: The Age of Innocence and The House of Mirth. In both, Wharton examines the strict moral and social codes of 19th century New York high society. Born into that world of wealth and privilege, she grew increasingly frustrated with its strict rules and double standards, especially regarding women’s expected behavior. She preferred the quiet confines of The Mount, her private estate in Lenox, Massachusetts, where she could breathe in corset-free comfort. In fact, she did most of her writing in bed!
While The Mount looks lavish to my untrained eye, it was actually revolutionary for its lack of excess. Wharton created a home that was bright and airy, in stark contrast to the dark and heavy Victorian style that was popular at the time. She designed the gardens following the same unpretentious principles and was enormously pleased with the result, even bragging to friends about her landscape gardening skills.
NORMAN ROCKWELL MUSEUM
Norman Rockwell is another iconic American artist who called the Berkshires home. For fifty years, Rockwell presented his idealized vision of New England life as illustrated covers for the Saturday Evening Post. These scenes often featured freckle-faced boys getting into mischief and quintessential American activities like baseball and family vacations. But Rockwell also tackled more serious issues facing the nation, such as entry into WWII and de-segregation. Many of his magazine covers and paintings are on display at the Norman Rockwell Museum in Stockbridge, where he lived and worked for 25 years.
STOCKBRIDGE
Stockbridge, Massachusetts was founded by English missionaries in the 1730s, but Norman Rockwell put the town on the map. His depiction of Stockbridge Main Street at Christmas became an instant classic. Today, aside from the cars and tour groups, the town appears little changed since being immortalized in 1967. The white-washed shops exude country charm and rocking chairs on the front porch of the Red Lion Inn beckon the weary.
MOHAWK TRAIL
The Mohawk Trail is a scenic drive through Massachusetts’ so-called Pioneer Valley. It follows Route 2 over a Native American trade route, hence the name. The trail’s symbol is a large bronze sculpture of a Native American called “Hail to the Sunrise,” but I somehow drove past without seeing it. I did stop for the “Elk on the Trail,” a WWI memorial erected by the Order of the Elks. The Mohawk Trail stretches for 63 miles through the Berkshire foothills, past charming towns, and breathtaking scenery. All the remaining attractions I mention below can be found on or near the trail.
MOUNT GREYLOCK
The Mohawk Trail begins in the Berkshires near Mount Greylock, the highest peak in Massachusetts. From the summit of 3,491 feet you can supposedly see five states, though they all looked the same to me. The drive to the top was much more exciting, with gorgeous scenery around every turn. I was stunned to find myself nearly alone on the road, especially in peak foliage season.
BRIDGE OF FLOWERS
My favorite stop on the Mohawk Trail is the Bridge of Flowers. In 1908, a trolley bridge was built across the Deerfield River connecting the towns of Shelburne and Buckland. But by 1927, automobiles had rendered the trolley obsolete. Rather than see the bridge torn down, the local women’s club decided to turn it into a public garden. The bridge has been covered with flowers ever since. I visited in October when the dahlias were out in all their glory.
GLACIAL POTHOLES
A short walk from the Bridge of Flowers is another interesting sight, the glacial potholes of Salmon Falls. These rock formations were carved 14,000 years ago during the last Ice Age, when water flooded the area and eroded the bedrock. Today it looks like a river of marble. The Deerfield River still flows but has been dammed near the potholes. The salmon that gave the site its name are long gone.
FRENCH KING BRIDGE
Continue driving east on Route 2 and you will cross the French King Bridge. This iron span was erected in 1932 and promptly named one of the most beautiful bridges in America. But it is the view of the Connecticut River you really want to see. There is a small parking lot on the western end and a pedestrian walkway so you can safely access the bridge.
WHERE TO STAY IN THE BERKSHIRES
There is an abundance of hotels and Inns all along the route which provide accommodations from luxury hotels to spas and bed-n-breakfasts.
Love to join you on these road trips. keep us posted!
Gary and Linda Speckman
Northville, NY
ERA Cobra #804
We should be back at the trips in the spring so will post up as we go.
Thank you