Travel + Leisure is exploring America one three-day weekend at a time. Here’s what to do on a short trip to Massachusetts’ cultural mecca.
Perfect 3-Day Weekend in the Berkshires
Credit: Jessica Antola

For about 80 years, the Berkshires area has been known as New England’s premier summer spot for culture-driven travel. It all started when the Boston Symphony Orchestra began decamping to the Western Massachusetts countryside from June through August in the mid-1930s to host a season of open-air concerts at what’s become the Tanglewood Music Center—a series that alone draws a whopping 350,000 visitors annually. Along the way, the region’s earnest farm culture and collaborative community have also given it a fine reputation as a top destination for delectable country cuisine.

These days, the Berkshires is more than arts and eats—though it’s certainly still got that in spades. There’s been a much greater focus on improving outdoor access and highlighting the region’s offerings beyond summer. If you have a car and are looking for a weekend filled with culture and nature, with great food to boot, follow this itinerary.

Day One

Before checking into your hotel, grab a quick lunch in Great Barrington and see what the Berkshires’ agricultural fuss is all about. Try local butcher Meat Market for a protein-heavy sandwich or a lunch board with charcuterie, cheese, and accoutrements. It’s a great place to experience the food community’s bond, too—its menu features cheeses from Rubiner’s, a neighboring vendor that makes a few mean grilled cheeses of their own.

Make your home base in Lenox or Pittsfield, both of which have a solid concentration of restaurants and shops. For the classic Berkshires experience, Lenox is where you’ll find the area’s most iconic properties: Blantyre, a Relais & Chateaux country mansion, the 16th-century palazzo-style Wheatleigh, and luxury wellness retreat Canyon Ranch. Pittsfield has a slightly more modern vibe, with a new contemporary boutique—Hotel on North—alongside the New England bed-and-breakfasts.

Your long drive is the perfect excuse to stay in and enjoy your hotel for an hour or two. But if you’re feeling antsy, return to Lenox for some boutique browsing before dining at local favorite Nudel—a cozy restaurant with nightly changing menus using only ingredients from small Berkshires farms. For a nightcap, head to Brava, a wine bar open until 1 a.m.

Day Two

Bright and early the next morning, taste some of New England’s best sourdough bread at Berkshire Mountain Bakery, then get the ultimate farm experience at Hilltop Orchards. Snack on pillowy cider doughnuts, sample wines and ciders, and hit the onsite trails for a quick hike (or, in winter, cross-country skiing and snowshoeing).

The rest of the day is all about what first brought the Berkshires to fame: its culture. Spend a few afternoon hours at the Massachusetts Museum of Contemporary Art or the Clark Art Institute (buy a combo ticket to save money). The former is housed on an airy industrial campus, with a mix of large-scale installations and various media—as well as a notable 105-piece Sol LeWitt exhibit. The latter, known for its Renaissance artwork and American paintings, is an architectural wonder set on a 140-acre oasis with vast meadows and landscaped walking trails.

A Tanglewood concert under the stars is a must for any summer visit. Still need to stock up for your picnic? Pick up artisanal cheese from Cricket Creek Farms on the way back from the museums, then hit up Pittsfield’s Guido’s Fresh Marketplace—the ultimate one-stop shop for organic fruit, international wines, ready-to-eat dishes, and other gourmet fare. We recommend getting to the concert grounds by 5 or 6 p.m.

Otherwise, catch a play this evening at one of the Berkshire’s accomplished local theater groups: Barrington Stage Company, Shakespeare & Company, and Berkshire Theatre Group. Satiate your stomach beforehand with Spanish tapas at Mission Bar & Tapas, or hang out over cocktails and international bites at the hip Methuselah Bar & Lounge.

Day Three

On your last day, it’s time to get active. In warmer months, feel the high at Ramblewild, home to an eight-course aerial park with 100-feet-high zip lines, or get moving at Pleasant Valley Wildlife Sanctuary, with 1,000 acres of wildlife-filled trails for all levels (including wheelchair accessible ones). In winter, Berkshire East Mountain Resort has the country’s largest mountain coaster in addition to the typical ski and snow fun.

If you’ve got time to spare on a summer visit, drive south to Jacob’s Pillow. The well-regarded dance school hosts a popular summer festival featuring more than 200 local and international dance acts, talks, and other events.

End the trip with a romantic step back in time with supper at Old Inn on the Green, once an 18th-century stagecoach relay. Dinner here is fine American cuisine—sourced seasonally and locally, of course—in intimate Old World dining rooms that are illuminated entirely by candlelight.

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