Just 2.5 hours north of New York City is Great Barrington, an eclectic, laid back town in the Berkshires of western Massachusetts. Do not make the mistake of comparing the Berkshires to the Catskills of upstate NY—the Berkshires have a unique vibe of their own. Here you’ll find rolling green hills, a deep sense of history (formerly known as the “Inland Newport”), fabulous art and music, and true farm-to-table restaurants that feel no need to label themselves “farm-to-table”.
There are a few quirky places to stay in the immediate area, such as the retro Briarcliff Motel, and the historic Red Lion Inn, just up the road in Stockbridge, offers a more refined stay. My recommendation, however, would be to rent one of the many beautiful old homes that the region is known for.
For food, Prairie Whale is a must, owned by famous (former) Brooklyn restaurateur Mark Firth. Most everything on the menu is from the immediate area (although it’s hardly advertised), and always features a staple (chicken, pork, veg) alongside a seasonal rotation of sides. The Saturday farmers market on Church Street runs from May-October, and here you’ll find everything from local coffee to handmade, wood-fired pizzas. 10-minutes from GB in the village of Housatonic is Berkshire Mountain Bakery, recently featured on Michael Pollan’s ‘Cooked’ and a rarity in that all Berkshire Mountain breads are naturally leavened with traditional sourdough fermentation.
Activity-wise, the hike up Monument Mountain is fairly difficult but quick, and well worth the views over the southern Berkshires and towards the Catskills that you’re rewarded with from the top.
And finally, if you can find the hidden Dream Away Lodge in Becket, you’re guaranteed an evening of great music.