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Massachusetts Travel >>> The Berkshires of Western Massachusetts

Ideas on How to Plan a Vacation in the Berkshires of Massachusetts
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Berkshire Scenery. Photo Credit: Ogden Gigli

Article by Eric H.

The Berkshires, located in western Massachusetts, feels like home. The quaint, close-knit classic New England towns, the gentle rolling hills and mountains, and the laid-back way of life create a scene that most people love to visit and, ultimately, find hard to leave.

It's really a "you had to be here" scenario as words cannot fully describe the feeling of traveling in the Berkshires. At first inspection, the Berkshires might be lacking in what other New England destinations have: the mountains are not as high as those in New Hampshire and Vermont and there are no really high-profile vacation towns with myriad outlets, souvenir shops, mini golf and ice cream places. Sure, you'll find a high peak like Mt. Greylock (at a modest 3,491 ft. elevation, and plenty of vacation attractions, but what stands out most about the Berkshires is the authenticity and purity of each town. Some are wealthy and upscale like Lenox and Stockbridge, others with a Mayberry RFD "every town" look like Lee, and communities that are struggling to make ends meet.  But whether rich or poor, almost all areas of the Berkshires offer splendid rural scenery, a classic New England scene in the form of a town common or tall white steeple church, and the opportunity to not be encumbered by too many hyped-up vacation towns. Perhaps that's why American artist and illustrator Norman Rockwell captured small town American life, through the paint, brush in this region. 

I remember first vacationing in the Berkshires, in the late 1960s, with my parents -- just north of Pittsfield at the Springs Motel and Restaurant. The Springs is no longer there, but what remains intact, to this very day, is the fresh mountain air, friendly hospitality and a geographical sense of purity and solitude that felt so nice as a child. Life was simple vacationing in the Berkshires as a kid: swim in a pool, take a nice Sunday drive with mountain views, dine at a restaurant with great food and friendly service, watch the sun go down in the big country sky, and get some sleep in the still and quiet night. Some things never change.

Having periodically gone back to the Berkshires in my young adult to middle-aged life brought more travel joys including spectacular fall foliage drives, going to fall festivals at several Berkshire town commons and relaxing by one of the most beautiful lakes at my uncle's condo further validated my love for this pristine, natural area.

The Berkshires really force one to relax, and who doesn't want that? Visitors may indeed choose to revel in the art of doing nothing, but, no doubt, have the option of experiencing wonderful outdoor recreation, cultural, and dining opportunities. 

There are so many ways to plan a Berkshires Mountains vacation -- there's really something for everyone of all ages. For starters, the Berkshires feature around 90 lakes and 90,000 acres of recreational land (golf, skiing, parks, etc.). Wow, what a great start! But wait, that's not all. The Berkshires of Massachusetts is home to the famous Tanglewood Music Festival in Lenox and prototypical charming Norman Rockwell-type Main Streets in Stockbridge, Great Barrington, North Adams (a work in progress but very appealing) and West Stockbridge.

Railroad St., Great Barrington. Photo Credit: Tim Grafft/MOTT

The aforementioned Mount Greylock boats the highest point in Massachusetts at a modest 3,491 feet, but the height just begins to tell the story: the "Hairpin Turn" affords absolutely spectacular 100-mile views of Massachusetts, Vermont, New York, Connecticut and New Hampshire. 

The Berkshires is equally appealing for all four seasons. The summer brings great lake swimming at places like Laurel Lake on Route 20, on the Lenox-Lee border. There's hiking at Mt. Greylock State Reservation in Lanesborough with 45 miles of trails, including the famous Appalachian Trail (also some biking and picnic opportunities). Fall time brings spectacular foliage no matter where you look -- and, as mentioned -- some really great town and village fall festivals and celebrations.  The experience is particularly impressive in the leafy town of Stockbridge and the hills and mountains around the Mt. Greylock area around Route 7. The Ashuwillticook Rail Trail is a 10-foot wide paved, 11.2-miles bike, roller blades and walking trail spanning from Lanesborough to Adams. In the winter, you'll find some impressive skiing at many ski resorts like Jiminy Peak in Hancock, Mass., with a decent vertical rise of 1,150 ft.  The spring brings a rebirth, of sorts, after a long cold winter  -- it's a great time to stroll the local towns when the crowds are fewer. The aforementioned Ashuwillticook Rail Trail can be used for cross country skiing, skiing and snowshoeing in the winter, according to the Massachusetts Department of Conservation and Recreation Web Site.

Art and culture remain an integral part of the Berkshires way of life, including the

Norman Rockwell Museum in Stockbridge celebrating "all things Norman Rockwell."

Mass Museum of Contemporary Art (MOCA), in North Adams, featuring a renowned, comprehensive and beautifully laid-out display of contemporary art.

The Berkshire Theater Festival, of Stockbridge, Mass., is one of the oldest professional regional theaters in the United States.

Hancock Shaker Village, an outdoor living history museum, in Pittsfield, wonderfully brings the Shaker story to life and to find meaning in the Shakers’ beliefs and culture.

The Berkshire Museum in Pittsfield offers a grand mix of arts, history and the natural world exhibitions, galleries, and attractions for the whole family.

And of course, Tanglewood...

Tanglewood Music Festival photo, Lenox, Mass.

Photo Credit: Kindra Clineff, MassVacation (MOTT)

The Berkshires also offers many shopping opportunities, including antiques, and locally-owned downtown service stores, boutiques and galleries in Lenox, Pittsfield, Great Barrington, Williamstown (wonderful, picture-perfect small town, home of Williams College), Stockbridge and Pittsfield. For the outlet shopping fan, you'll find the Prime Outlets in Lee, Mass. featuring more than 65 outlet stores, including Cole Haan, Michael Kors, Nike Factory Store, and Under Armour. Not the highest profile outlet complex, but quite serviceable.

Of course, you'll find some classic New England inns, resorts, hotels and wellness facilities, including:

The Wagon Wheel in Lenox is affordable, family-oriented and a delightful throwback to the motels we grew up with in the 1960s and 70s. The value and its central location make the Wagon Wheel a good choice for lodging in the Berkshires.

Wheatleigh, also in Lenox, offers an upscale lodging experience, combining the "perfect marriage of the grandeur of a 16th century Florentine palazzo with the elegance and comfort of the 21st century."

The Red Lion Inn, in Stockbridge, features a great, big-old front porch to relax and old world hospitality. From the slight elevation of the porch, you can seem true America at its best --the charming little shops, the wide sidewalks and street, kids riding their bikes, the lovely churches, and the splendid diverse New England architecture of the town, to name a few. The inn dates back to 1773!

A Berkshires dining spot we love:
The Elm Street Market at 4 Elm St. in Stockbridge will bring you into small-town America with its informal luncheonette -- complete with stools and counter -- in an old time market that hearkens back to a previous generation. Nothing fancy, but great sandwiches and lots of local conversation!

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