Are We There Yet? – The Berkshires

Traveling to Western Massachusetts.

Jennifer Coxby Jennifer Cox

I love New England. It's quaint and charming and it's a great place to catch up on some R&R. The sights are beautiful, the accomodations are top-notch, and the food is nothing short of extraordinary (especially if you're a seafood lover).

The next place I'm definitely hitting up is the Berkshires. It’s the 75th anniversary of their world-renowned music festival Tanglewood, which is celebrating with a number of new digital initiatives where you can view streaming master classes and download historic performances throughout the past 75 years, as well as attend world premiere performances and events with appearances by celebrities (i.e. John Williams, James Taylor, Yo-Yo Ma, etc.). There’s a rich story about how this unknown outpost in the Berkshires grew to be one of the world’s most influential destinations for advanced study, making a $60 million impact on the Berkshires economy each summer. In addition to classical performers, Tanglewood drew leading artists of various generations including Bob Dylan to Janis Joplin to The Who, as well as Earth, Wind & Fire to Tony Bennett to Wilco. Visitors can have the best of country and culture at Tanglewood, located in the picturesque Berkshires (only 2.5 hours from NYC and Boston), from savoring an artisanal picnic basket under the summer stars on Tanglewood’s lawn while listening to legendary performers to visiting new exhibitions of cultural institutions such as the Norman Rockwell Museum, Clark Art Institute or Mass MoCA and more.

Here are some places where you can eat and stay in the Berkshires:

– Opened in August 2011, The Meat Market is the coolest new butcher in Great Barrington. It’s offering locally-sourced meats as well as sandwiches, snacks and homemade stocks. Great for picking up treats for your Tanglewood picnic basket.

– Another new hotspot is Crossroads Café, which opened in Hillsdale, NY (about eight miles from great Barrington and about 25 minutes from Tanglewood). Sort of farmhouse style, but casual and fun. Photogenic and very cool Butcher paper, communal tables, chalkboard menus, etc.

– Rubiners has a great cheese selection. They have a sandwich spot in the back, called Rubi’s, with amazing paninis, beer and coffee tpp.

– British couple Clare & Richard Proctor left their previous lives working in magazines in London in order to renovate the Briarcliff Motel in Great Barrington. It’s a classic 1960 motor lodge at the foot of Monument Mountain and is being turned into a hip hotel with 16 rooms. They will serve some food, and they’re developing the six acres behind the property into hiking trails. Low price point, high design.

Bon Voyage,



Jenn Cox is a Montreal-based freelance journalist. Visit her website or email her at