REAL NEW ENGLAND TRAVEL: The Scenic, Welcoming Berkshires of
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
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...
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
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.
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
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
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,
Norman Rockwell Museum in
Stockbridge celebrating "all things Norman
Mass Museum of Contemporary Art (MOCA),
in North Adams, featuring a
renowned, comprehensive and beautifully laid-out display of
Theater Festival, of Stockbridge, Mass., is one of the
oldest professional regional theaters in the United States.
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
And of course, Tanglewood...
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!
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.
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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VisitingNewEngland.com Publisher Eric Hurwitz
Town Greens -- Discover New England's first travel attractions:
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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