On the western edge of Massachusetts, Berkshire County stretches north-south for 60 miles, from the Vermont border to the Connecticut state line. Its vast beauty is too much territory to cover in a long weekend—but thankfully, visitors don’t have to.

The excitement has been traditionally clustered at the southern end, framed by the four towns of Lenox, Becket, Great Barrington, and West Stockbridge. But now, so-called “North County” is equally as compelling.

Pointing the compass northward affords visitors a unique look at the natural splendor and history of the Berkshires. The geographical center of this up-county area is the sigh-inducing college hamlet of Williamstown, which is flanked by a pair of little cities, Pittsfield and North Adams, each artfully reborn out of a faded industrial past.

Photo: Hotel on North

Photo: Hotel on North

Begin your loop at the compact Pittsfield Municipal Airport—transfer there from your Tradewind flight to a well-appointed rental SUV, and in just minutes, you will have pulled up at Hotel on North, a 45-room boutique hotel that became the beating heart of Pittsfield’s downtown from the day it opened in 2015. A former menswear and sporting goods emporium, the building today is a tour de force of preservation-based remodeling, its good bones exposed and its interiors jazzed up with repurposed trim elements from the distant past. The hotel’s highly popular restaurant, Eat on North, is run by former White House chef Ron Reda.

Take the evening and part of the next day to ramble Pittsfield’s downtown and decide whether all those “Brooklyn of the Berkshires” claims are well-deserved. From District Kitchen and Bar on West Street up to Methuselah at the corner of North and Bradford to the tapas and wine bar Mission a block away, the town’s dining and drinking options invoke rustic-chic sophistication among old-city walkability. Boutiques and retro shops are in abundance, including such favorites as the décor-centric Dory and Ginger, Steven Valenti’s Clothing, and the Berkshire General Store. Morning coffee and first-rate baked goods are steps away at Dottie’s coffee shop, which also boasts the kind of meeting-place vibe that convinces people to move to resurgent communities like this.

Photo: Mission Berkshires

Photo: Mission Berkshires

Route 8 out of Pittsfield takes you along the eastern edge of the 12,000-acre Mount Greylock State Reservation. It’s named for the state’s highest peak and laced with upland trails that will carry a hiker deep into the heart of a New England summer. On this trip, you may want to stop by the visitor center and pick up a trail map, in case you’re inspired to plan an outdoorsy return to the area amid October’s cooler air and bonfire-hued foliage. If you opt to skip the park and cruise directly from Pittsfield to North Adams, you’ll be there in less than 30 minutes most days.

What you’ll find on arrival is a pocket-sized city, still somewhat in recovery from a mid-1980s economic blow — but blooming back to life with plenty of charm. Today, the largest museum of contemporary art in the U.S., the Massachusetts Museum of Contemporary Art (or Mass MoCA), occupies a 24-acre campus originally built by Sprague Electric, the space-mission contractor that supplied NASA and other federal agencies with advanced circuitry and components till its closure (leading to the town’s aforementioned economic downturn).

Photo: Mass MoCA via Grace Clark

Photo: Mass MoCA via Grace Clark

To display the works produced by contemporary art superstars like Sol LeWitt, Laurie Anderson, and Robert Rauschenberg takes vast amounts of inexpensive space — much more than the name-brand museums in big cities have available, but perfectly suited for this unlikely space in The Berkshires. Combine the need for acreage with creative vision, and you’ve got a gritty town fast on the rise whose principal industry is modern art. Odd as that may sound, Mass MoCA reportedly boosted local economic activity by $51 million in 2017 alone.

You soak up the “anything’s possible” zen of North Adams by staying at The Porches, a chic hotel on the Mass MoCA property, or perhaps at the brand-new Tourists, a self-styled “riverside retreat inspired by the classic American roadside motor lodge.” Investors from the California foodie scene designed and built Tourists and its food-and-beverage amenities, featuring a new lounge, The Airport Rooms, serving classic cocktails and a “creative roadhouse” menu. Its executive chef, Corey Wentworth, was recruited from Boston’s Flour Bakery.

Photo:  Tourists via Peter Crosby

Photo: Tourists via Peter Crosby

The artwork at Mass MoCA is vast in scale, which means you go through it more than past it, which makes the appreciation experience looser and more fun. Performing arts further increase the hip factor here — there are film screenings, rock concerts, comedy festivals, and other on-stage exuberance. The beloved and versatile band Wilco has a particular footprint at Mass MoCA, most notably thanks to its biennial Solid Sound Festival — this year, the Wilco event happens June 28th through 30th.

Also on campus is Bright Ideas Brewing, a craft brewery and taproom. Meanwhile, any left or right you take in the general vicinity of the campus will reveal some semi-pro mural or sculpture to echo the crown jewels of the museum. Admittedly, most of us lack the endurance to study art for entire mornings or afternoons — but that’s not the point here. A day in North Adams is actually akin to life inside a “60 Minutes” segment, with socioeconomic and cultural history being made in real time. (If you’re quiet, you can hear the property values rising.)

Fifteen minutes east is prim, prosperous Williamstown, where the top-ranked liberal arts college in the country (per U.S. News) seamlessly merges its verdant campus with the commercial layout of the town. In the summer, the cultural scene around Williams College is ever vibrant. This season, the Broadway-quality dramatic offerings at the Williamstown Theater Festival include one play that’s particularly easy to recommend. It’s a revival of Henrik Ibsen’s Ghosts starring Golden Globe and Academy Award nominee Uma Thurman, on stage through most of August. Meanwhile, the Clark Art Institute has a high-powered French Impressionist exhibit, titled “Renoir: The Body, the Senses,” devoted to Renoir’s unsurpassed achievement in the depiction of body figures.

Photo: Mezze Bistro & Bar via FED Guides

Photo: Mezze Bistro & Bar via FED Guides

Dining in Williamstown won’t disappoint—perennial favorites include Mezze Bistro & Bar as well as The ‘6 House and Pub, a few minutes outside of town in a rural setting. The Water Street Grill is just right for high-quality tavern fare and live music. Tucked around the corner from Spring Street's shops, pubs, and restaurants is one of the half-dozen best public golf courses in all of New England, Taconic Golf Club. An early-20th-century classic by Stiles and Van Kleek, Taconic is owned by the college, meticulously maintained at all times and recently renovated by Gil Hanse, the most renowned course architect working today.

When your three-stop tour is over, it’s time to head south down historic Route 7 toward Pittsfield, enjoying sublime Berkshires scenery plus endless roadside attractions, from antiques to ice cream to riverfront picnic grounds. An easy hour’s ride on an old country highway, it’s ideal for reflecting on the artsy, urban fascination you’ve encountered while letting the innocence of rural New England summertime float by.


Tradewind offers private charter flights to the Berkshires year-round on a fleet of Pilatus PC-12s. To reserve a charter, call us at 1-800-376-7922 or click here.

Featured Photo: Tourists via Nick Simonite