Home to Williams College and two nationally lauded cultural attractions—The Clark Art Institute (which now features a free, year-round outdoor exhibition, Ground/work) and an eponymous Theatre Festival—Williamstown, Massachusetts anchors an idyllic section of the Berkshire Mountains. Williamstown is more than a historic New England outpost surrounded by pastoral beauty; it’s the eye in a storm of exciting culinary explorations, hospitality ventures and world-class art—some of which can be found just across the border in Vermont or in neighboring Massachusetts towns. Perhaps, the ultimate joy of the Berkshires, however, is that each season is beautiful in its own way, too.
A wood-clad riverside design hotel, TOURISTS—in neighboring North Adams—offers stylish accommodations for all types of travelers. Due to the fact that the property contains only 48 rooms and the design embraces natural materials and includes rear windows to the Hoosic River, TOURISTS feels comfortable and calming. A wander over the river and along close-by paths reveals plenty of nature and some surprising sculptures. Also outdoors, community options like fire pits and heat lamps allow for safe gatherings over signature cocktails. Its location makes it an ideal central hub to explore the greater region, as well.
Mezze Bistro + Bar
Williamstown’s Mezze Bistro + Bar is a culinary highlight to any trip to the region. A pioneering voice in the region’s farm-to-table movement, the menu’s contemporary American cuisine emphasizes wholesome dishes with local ingredients. The bistro’s current location—where it’s been since 2010—sits on several acres of land that overlooks Sheep Hill. The restaurant itself brings to life a historic building from the 19th century. Outdoor dining is an option on the property’s charming (and heated) porch and lawn. A solid alternative, we’d also recommend eating and drinking at The Barn in the Williams Inn, which recently opened in a new location in town in an all new building with beautiful views.
A requirement for art adventures, North Adams’ MASS MoCA tends to attract visitors with its mesmerizing multi-work James Turrell installation or its mind-blowing, multi-floor commitment to the career development of Sol LeWitt. While these long-term installations may be the initial draw, it’s everything else (from Jenny Holzer’s poetic works to Victoria Palermo’s bus stand) and it’s impressive seasonal shows within this sprawling former factory that makes it an uncompromising contemporary art institution. Plan to stay for several hours—and book your Turrell appointments in advance. On the MASS MoCA campus, be sure to hit up A-OK BBQ or Bright Ideas Brewing for post-art snacks and beverages.
Formerly a cotton mill, and named after local Mount Greylock, the 240,000-square-feet of Greylock WORKS in North Adams now hosts a creative co-working space, food program incubator and a craft distillery (home of Forager Gin and Ski Bum Rum). It’s also an event space and residence. Be sure to check out the Berkshire Cider Project tasting room while there. The family-owned dry, sparkling hard cider brand produces from 100% Berkshire apples and they do not add extra sugar.
Purveyors of cannabis wellness products, Williamstown’s Silver Therapeutics is a locally owned and operated dispensary (with online orders accepted in advance). Their high-quality operation stocks everything from raw buds and pre-rolled joints to concentrates and edibles. Their “budtenders” also happen to be friendly and knowledgable. It’s a great way to discover Massachusetts’s legal cannabis products.
Taconic Crest Trail
No time in the Berkshires is complete without a hike and the Taconic Crest Trail is one of the Berkshire region’s finest. Remarkably, this 37-mile stretch straddles the New York State and Massachusetts border at times, and later New York and Vermont. You can enter from Williamstown, via the ascending Phelps Trail, and continue on or loop out.
Pownal + Bennington
From Williamstown, Route 7 crosses into Vermont and the Green Mountains. In only a matter of minutes, travelers pass through pastoral Pownal and ten minutes later into Bennington. The quaintness of downtown Bennington mirrors that of Williamstown—though in a relaxed manner. Take in the view from The Bennington Battle Monument and visit Bennington Potters and the Bennington Bookshop (Vermont’s oldest independent book store); both worth the side trip, too.
Hero image by Josh Rubin