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REAL NEW ENGLAND TRAVEL: The Scenic, Welcoming Berkshires of Western Massachusetts

Williamstown, Massachusetts
 Williamstown, Massachusetts in the fall.

Article by Eric Hurwitz, as well as photos unless otherwise noted. Updated 8/18/17.

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The Berkshires, located in western Massachusetts, feels like home. The quaint, close-knit classic Massachusetts 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. This is real New England travel, at its finest.

It's 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 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. Recently, I traveled back to the Berkshires while writing a book, Massachusetts Town Greens, that features the most beautiful, significantly historic town commons in the state. The Berkshires have so many nice town commons that fit in perfectly with the region...

Williamstown town common in Massachusetts
Town common in Williamstown.

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. Sometimes, a nice Sunday drive is enough...

Scenic Route 2 drive in the Berkshires of Western, Massachusetts
Somewhere on Route 2 in the Berkshires.

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 Lee, Stockbridge, Great Barrington, North Adams (a work in progress but very appealing) and West Stockbridge.

Downtown Lee, Massachusetts, is one of the most charming towns in the Berkshires.
Downtown Lee, Massachusetts.

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.

Hairpin Turn, Berkshires of Western MassachusettsHairpin Turn, Charlmont, Massachusetts.

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.

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, Berkshires of Western Massachusetts
Tanglewood. Photo credit Massachusetts Office of Travel and Tourism Flickr page at

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 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!

Red Lion Inn, Stockbridge, Mass. Red Lion Inn, Stockbridge, Massachusetts. Photo credit: Massachusetts Office of Travel and Tourism at

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.

Berkshires dining spots we love:
While writing my newest book, Best Diners in New England at 85 Center St. in Lee, we came across Joe's Diner. Unassuming in appearance with a plain "Joe's Diner" sign and an old-time Pepsi sign above, American flags in the window, a wooden bench and flowers near the entrance, we then stepped inside to another time and place where local customers and waitresses conversed over big ´┐╝portions of classic comfort foods like burgers, turkey sandwiches, pancakes, corned beef hash and signature drinks like coffee, root beer and milkshakes. Looking around the room suggested a sense of history and community pride. Colored drawings from elementary school students saturated one side of the wall. Photos of celebrity visitors -- the DiMaggio brothers and U.S. Secretary of State John Kerry, to name a few -- lined another wall. Most prominently, that famous Saturday Evening Post drawing known as The Runaway -- a friendly policeman talking with a small would-be runaway boy at a diner -- stood out from everything else on the wall, given its legendary pop culture status. You see, Joe's Diner was reportedly once part of the inspiration for Norman Rockwell to come up with that masterpiece.

The chance to be introduced to a very nice town, connect with the community in the diner and have seasoned waitresses --as opposed to disinterested employees serving you in between their texting and social media empires -- is a modern day revelation. Joe's Diner taps into that nostalgia by slowing down the pace from our higher speed highway routes, and getting down to the basics. It is part of the America we used to know, and that, happily, still exists in some neighborhoods to this very day.  I highly recommend  it!

Joe's Diner in Lee, Massachusetts
Joe's Diner in Lee.

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!best pizza is the one you like the most.

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The Berkshires of Western Massachusetts is ideal for a vacation filled with mountain and lake scenery, relaxation, quaint small towns and culture.

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Books by Publisher Eric Hurwitz

Massachusetts Town Greens -- Discover New England's first travel attractions: town commons!

The Best Diners in New England -- If you love classic diners, New England has them! In my book, I write in detail on 50 top local diners.

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