A Brief Break in the Berkshires

It took us a very long time to visit the Berkshires, a rural region in the mountains of western Massachusetts that is popular for hiking, skiing, relaxing, fall foliage peeping and perhaps most famously, soaking up culture. The Berkshire region is noted as a center for the visual and performing arts.

Just a few hours from Fairfield and Westchester counties, the Berkshires make for a great weekend getaway. I am surely not an expert after spending just 48 hours there, but I think this weekend visit gave us a solid, basic overview of the area. 

Beginning from the town closest to home, below is a brief summary of the areas we visited in the Berkshires:

Great Barrington - This town is probably the most similar to the hip hotspots of the Hudson Valley. It’s got a nice, bustling and happening walkable downtown area. And it showcases a progressive, artsy spirit. We spent a few hours exploring the many adorable shops of Great Barrington. If visiting with your kids, a stop at Robin’s Candy is must do as well as Tom’s Toys. We adults loved Depart Wine and ogling over the vintage barware at Robert Lloyd Gallery. At least a handful of spots in Great Barrington have a second location in Hudson, Rhinebeck, etc, further strengthening the similarity between this town and the nearby Hudson Valley.

Stockbridge - Right nearby Great Barrington, Stockbridge feels small and quaint and more New England than Upstate NY. There isn’t too much of a downtown area in Stockbridge but what is there is very pretty (The Red Lion Inn is a popular place to stay and dine in Stockbridge; we’ll have to try it next visit) and this town is “must visit” as the location of the beautiful (but tiny) Norman Rockwell Museum.

Lenox - Lenox feels like the center of the Berkshires. It’s more built up, more adult oriented and more luxurious than the nearby towns (and most of the towns of the Hudson Valley). On the flip side, the Berkshires generally seem to attract an older crowd, and Lenox in particular was filled with folks at retirement age.

Lenox is the location of Tanglewood, a stunning, world class outdoor performing arts venue that houses the Boston Symphony Orchestra in summer. Also in town is The Mount, author Edith Wharton’s beautiful former home and garden.

We had a nice meal at Brava in Lenox before heading to Tanglewood - but it’s also really fun to pack a picnic to enjoy on the lawn along with your performance.

North Adams - Quite a bit north from the previously mentioned towns, North Adams is still rather run down and industrial. I wouldn’t recommend visiting for the town itself, BUT without a doubt, North Adams is worth visiting for MASS MoCA, one of the largest contemporary art museums in the world. A visit here was the impetus for our trip to the Berkshires and it did not disappoint.

We stayed at The Porches Inn for our weekend in the Berkshires and it is mere steps from MASS MoCA. The hotel is a set of former row houses, now refurbished and connected by a - you guessed it - large porch that overlooks the museum. The hotel is charming and distinct (but note that while it is nice, it is not a luxury hotel) and has a cozy pool, hot tub and indoor and outdoor sitting areas. In North Adams, we had a nice breakfast at The Break Room.

Williamstown - The location of prestigious Williams College, Williamstown is a small college town just west of North Adams. The Clark Institute is here, along with a lot of New England charm. We also had an incredible and special meal at Mezze Bistro + Bar in Williamstown.

The Berkshires are a great little getaway for the weekend!