48 Hours In The Bucolic Berkshire Mountains Of Massachusetts

Internally, I have been waging my country mouse vs. city mouse debate since birth -it’s my personal ping pong game. I adore NYC yet it sure feels really fine when I am able to leave a vertical, stimulating, dense city and travel into the horizontal, pristine and spacious countryside. My eyes immediately welcome a greener world.

However, my mid August drive up to the Berkshires convinced me that I don’t necessarily have to make a choice…I can readily and very easily have both.

The Berkshire Mountains are not only a locale, but a mindset…true soul food for the mind and body. And by car, it’s an easy, uncluttered 3 hour drive into this peaceful, western corner of Massachusetts where no structure seems higher then two stories, and civility rules. Should you be looking for a get away- yet not far away – then head north for the brio and bravura of the Berkshires.

Photo Credit: http://blog.massdrive.com

How to Get There

Such a gorgeous, fun, easy drive, especially in the Fall with its magnificent colors…highly recommend you travel by car via the entire length of Taconic State Parkway North which you can pick up from the Saw Mill River Parkway off the Major Deegan (I 87 North). There is bus service (Peter Pan) from Manhattan, and taxi call service once there should you only wish to stay in one town.  But with so much to do, a car is your best bet.

Where to Stay

Cannot say enough good things about the calm, comfortable, reasonably priced Briarcliff Motel, on Route 7. This was a find!  Their location is ideal for your visit, situated between the picturesque, charming towns of Stockbridge and Great Barrington with the Monument Mountains in the forefront. Comprised of 16 ultra cool one story units, with a hip minimalist décor, this is the perfect launching point for any site you wish to visit during your stay.  The owners, Richard and Clare and their assistant, Kate, are sharp as cut glass, incredibly knowledgeable about this area, and helpful in any and every way possible. Their complimentary communal breakfast table – highlighted by flavor packed healthy home made scones and muffins – added a homey touch to my stay as well as encouraging informative, interesting conversation with fellow guests.

Photo Credit: http://thebriarcliffmotel.com

What to See

The question is not what to see, but where do I begin? The joy of this corner region of MA is the fabulous diversity of sites and events. There’s something for everyone.

If you crave culture, there is the legendary “Tanglewood” for classical music outdoors on a midsummer’s night.  “The Hedge” is the setting for the Boston Symphony Orchestra summer concerts with the “Ozawa Hall” for daring, modern classical music, and “Jacob’s Pillow” for dance performances.

Wind your way to “Shakespeare and Co.” or the “Barrington Stage Co.” should you desire some excellent repertory theater.

Photo Credit: Kevin Sprague

The “Norman Rockwell Museum” and “Chesterwood”- home to sculptor and artist extraordinare, Daniel Chester French – will well attend your artistic sensibilities.  (Our full Rockwell review can be read here.)

Photo Credit: http://www.wikipaintings.org

Should you wish to follow America’s literary thread, don’t miss “The Mount,” the cultured, softly groomed estate of Edith Wharton and my personal favorite, “Arrowhead,” the more down-to-earth, domestic homestead of Herman Melville.

Photo Credit: David Dashiell

Try to schedule visits to the gracious manor homes of the Gilded Age i.e. “Ventfort Hall” and “Naumkeag” and visualize a life of gardens, waltzes and fine country living at the turn of the century.  The historic inn, “The Red Lion,” located on Stockbridge’s notable Main Street and immortalized by Norman Rockwell in an iconic Christmas painting, merits a major stop. An oasis of antiques and country elegance, have a drink outside on their panoramic porch. Or better yet, cap off you day and extend your evening with a drink and some informal “join in the joy” music in “The Lion’s Den.”

Photo Credit: http://www.dispatch.com

What to Do

1. The summit of Mt.Greylock in Lanesboro beckons, by foot or by car. Start at the Visitor’s Center, which is also a compact museum representing the natural world and history of Mt.Greylock. Here you’ll also find maps and information on the hikes, amazing wildlife and natural world that awaits you, as well as the route of the parallel eleven mile stretch of the Appalachian Trail.  Should you prefer, you can slowly drive your car up (there are some hairpin turns) via the scenic road laid out in the 1930s by the admirable Civilian Conversation Corp. When you reach the summit, it is capped by an historic War Monument, and the legendary, albeit, closed, daring Thunderfoot Ski Trail. Enter the Bascom Lodge to savor a glorious view from some 3,400 feet up, then dine here with the clouds in the majesty of the mountains. Magnificent.

2. You’ll need as much time as possible at the huge Jiminy Peak Mountain Resort in Hancock, an affordable, action packed, outdoor adventure park. This is a family friendly, interactive experience. Enjoy “The Climbing Wall,” “The Scenic Chair,” “The Alpine Slide,” and “The Soaring Eagle.” Then challenge yourself with rope bridges, ladders, zip lines and scramble nets.  Close an adrenaline filled day with mountain dirt biking down an obstacle course out of an action movie. In winter, enjoy its ski and snowboard trails. This is one stop shopping — dining, homey accommodations and adventures galore.

Photo Credit: http://www.jiminypeak.com/

3. “One touch of nature makes the whole world kin” at Hancock Shaker Village.  Such a splendid, uncluttered site, spend an entire day here while exploring this lovingly restored village. Simplicity, practicality and a natural spirituality guided the Shaker sect; learn not only their pragmatic approach to daily life and worship, but relish the opportunity to interact with a self sufficient, working farm, complete with pigs, hens, sheep, chickens, dairy cows and goats. There are tours, demonstrations, and interactive exhibitions all surrounding village life. Crops, gardens and growth abound. Some 20 interesting Shaker buildings are open to visit, but don’t ignore the simple glory of a day outdoors on the grand grounds of this special, unique site.  (The full review can be read here.)

Visit the beautiful Berkshires in any season; it’s a true transcendental experience. Drive home rejuvenated, refreshed…and ready to return!


By: Joanne Theodorou


A very special thank you to the wonderful folks at the Berkshire Visitors Bureau!




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