Great Barrington, Berkshires

Tucked away in the Berkshires of Western Massachusetts sits Great Barrington—dotted with its postcard perfect brick-clad storefronts and circa 1905 theatre. For well over 100 years artists, writers and other creative types have turned the town into a four season destination where visitors and locals alike can enjoy hiking, skiing and an award-winning restaurant scene.

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1. The Skiing

With easy in-town access, as well as the surrounding Berkshires, Butternut offers 11 lifts across 110 acres of variable terrain suited for beginners to the advanced. Check out the Twisted Terrain Park loaded with natural features, like log rides and rock jibs, and two impressive jump lines ranging from small tables, to more classic 30 foot step-downs.


2. The Art

Housed in the historic Mahaiwe Bank, The Vault Gallery is a hidden jewel on trendy Main Street showcasing a creative take on the picturesque beauty of the Berkshires. What's your favorite?


3. The Cocktails


After exploring the picturesque scenery and culture that makes Great Barrington a charming destination in the Berkshires, stop by John Andrews Farmhouse for one of their unique handcrafted cocktails—we can't help to recommend the prohibition-era "Bee's Knees," concocted with botanist gin, lemon, honey and lavender. If you're enjoying the view of the circa 1700s farmhouse's original ice house you've tallied yet another reason to stay for dinner. Led by Chef-Owner Dan Smith and inspired by international flavors using seasonally sourced ingredients—the restaurant holds a strong commitment to locavore principles supporting local farmers and artisan food makers in the Berkshires, Hudson Valley and Northwestern Connecticut. Signature favorites include Trout Filet stuffed with spinach, Seared Duck Breast and house-made Ricotta Gnocchi.


4. The Hiking

From the 1,642 foot summit of Squaw Peak, you’ll enjoy views from Mount Greylock to the Catskills of New York. The nearly 2 mile loop Indian Monument Trail brings hikers past more than 300 years of history—the remains of ancient Native American trails, stone walls of former sheep pastures, cart paths that brought hemlock bark to tanneries, hearths of charcoal makers, and you might even see the occasional bald eagle soaring gracefully above the serene Housatonic River Valley spreading below.


5. The Theatre

In continuous operation since 1905, the elegant Mahaiwe Performing Arts Center offers an exciting night out in the Berkshires with live performances throughout the year—including everything from ballet, cinema, opera, musical acts and so much more.