Berkshires

The Berkshires occupy a particular place in the New England imagination — the place where Bostonians and New Yorkers have both always gone to escape, a meeting ground of high culture and rolling rural landscape that doesn’t quite belong to either state’s dominant character. Edith Wharton lived here. Herman Melville wrote Moby-Dick partly here, within sight of Mount Greylock (which he compared to a whale’s hump). Nathaniel Hawthorne lived in Lenox and was close friends with Melville. The Boston Symphony Orchestra has summered at Tanglewood since 1937. Jacob’s Pillow has been the birthplace of American dance since 1933. The density of cultural history in these hills is genuinely extraordinary.

I’ve been to Tanglewood twice. The first time was a July Saturday to see the BSO perform — I bought lawn tickets ($25), brought a blanket and a picnic, and spent three hours under the stars listening to Beethoven while the fireflies competed with the outdoor lights. The second time was a Sunday morning rehearsal — open to the public, essentially free, with the orchestra in the Shed working through the program at a fraction of the Saturday night performance cost and atmosphere. Both were excellent in completely different ways. Tanglewood is one of those places that would justify a whole trip on its own.

MASS MoCA in North Adams is the other anchor, and the contrast with Tanglewood is instructive. Where Tanglewood is elegant pastoral Americana — white linen tablecloths on the lawn, Boston Brahmin summer colony — MASS MoCA is industrial and contemporary, housed in a 26-building factory complex where the contemporary art installations are often building-scale. James Turrell’s light art, Sol LeWitt’s massive wall drawing (the largest in the world), and Laurie Anderson’s multi-floor installation have all lived here. The museum’s scale allows artists to work at ambitions that other museums can’t accommodate.

The drive from Pittsfield south through Lenox and Stockbridge on Route 7 in October is legitimately one of the finest fall foliage drives in New England — rolling hills, church steeples, farm stands selling cider and mums, and the whole landscape looking like a Norman Rockwell painting (which is appropriate, since his studio is in Stockbridge). This is the Berkshires moment that most people are imaging when they imagine the Berkshires.

Why the Berkshires belong on your New England itinerary

The Berkshires are New England’s cultural countryside — a region where the arts infrastructure is so strong that you can see world-class performances in converted factories, on concert lawns, and in dance barns, while staying at 18th-century inns in villages that still look substantially as they did when Edith Wharton was their most prominent summer resident.

The arts calendar is extraordinary. Tanglewood runs from late June through August. Jacob’s Pillow Dance Festival runs late June through late August. The Williamstown Theatre Festival (Williamstown, in the northern Berkshires) runs late June through August and regularly sends productions to Broadway. Shakespeare & Company in Lenox performs summer through fall. The Clark Art Institute in Williamstown has one of the finest collections of French Impressionism outside Paris. This level of cultural programming in a rural landscape is genuinely unusual anywhere in the world.

The fall foliage in the Berkshires peaks about a week later than the White Mountains — typically late October — and the combination of rolling hills and mixed hardwood-conifer forest produces a more sustained color display than the more dramatic but briefer mountains to the north. Route 7 through Lenox and Stockbridge, and the secondary roads between Sheffield and Great Barrington, are among the most beautiful fall drives in Massachusetts.

What should you do in the Berkshires?

Tanglewood — The Boston Symphony Orchestra’s summer home in Lenox is one of America’s great musical institutions. Lawn seats run $25-$35 and give you the same music (and the outdoor experience) as the $120 Shed seats. Bring a blanket and a picnic, arrive an hour before the performance for good lawn position, and plan your trip around a Saturday evening BSO program in July or August. The Sunday morning open rehearsals are a budget alternative — check the schedule at tanglewood.org.

MASS MoCA — Massachusetts Museum of Contemporary Art, in a 26-building 19th-century factory complex in North Adams, is the largest contemporary art museum in the United States and one of the most innovative in the world. The Sol LeWitt retrospective (a permanent installation of 105 wall drawings) fills an entire building. James Turrell’s light installation occupies another. Budget a full day. $25 adults.

Norman Rockwell Museum — In Stockbridge, the museum holds the largest collection of Rockwell’s original paintings and is housed in a building designed by Robert A.M. Stern. Rockwell’s actual studio was moved to the museum grounds. The collection makes the case for Rockwell as a genuine American master rather than a commercial illustrator — a case that’s increasingly accepted. $22 adults.

Mount Greylock — The highest peak in Massachusetts (3,491 feet) has a paved auto road to the summit, a summit lodge (Bascom Lodge, run by AMC), and views into four states on clear days. In October, the summit view over the color display in the Hopper amphitheater below is extraordinary. The Appalachian Trail crosses the summit. $5 vehicle fee.

Clark Art Institute — In Williamstown, the Clark has one of the finest collections of French Impressionism and American art outside major metropolitan museums. The Renoirs, Monets, and Sorolla holdings are particularly strong. The building complex by Tadao Ando (2014 expansion) is architecturally significant. $20 adults; free November through May.

Stockbridge Village — The village that Norman Rockwell painted repeatedly is preserved in a condition that makes the paintings make sense. The Red Lion Inn (1773, still operating) on Main Street is the center of town. Walk Main Street in any season and understand why Rockwell chose this place.

Jacob’s Pillow Dance Festival — America’s oldest international dance festival, running from late June through late August in a converted barn complex in Becket. Free outdoor performances on the natural stages most afternoons; ticketed evening performances in the Ted Shawn Theatre from $35-$85. The most important summer dance venue in the US.

Where should you stay in the Berkshires?

Budget ($60–$100/night) — The Berkshires Hostel in Lenox is a rare budget option in an expensive region. Chain motels on Route 7 in Pittsfield run $70-$90. Great Barrington has some Airbnb options at lower rates than the more polished Lenox and Stockbridge areas.

Mid-Range ($130–$220/night) — The Porches Inn at MASS MoCA in North Adams is directly adjacent to the museum in converted mill-worker row houses — an excellent choice if MASS MoCA is the priority. The Briarcliff Motel in Lenox is unexpectedly charming at $120-$160 in shoulder season. The Williams Inn in Williamstown is reliably excellent.

Luxury ($300+/night) — Wheatleigh in Lenox is a 1893 Florentine palazzo on 22 acres, a Relais & Chateaux property with outstanding cuisine — the most prestigious address in the Berkshires. Canyon Ranch in Lenox is a full wellness resort that draws celebrities and executives for weeks at a time.

Where should you eat in the Berkshires?

• Mezze Bistro & Bar (Williamstown) — The best restaurant in the northern Berkshires, with a farm-to-table menu and excellent wine list. Worth the drive from anywhere in the region. $45-$65 per person.
• Prairie Whale (Great Barrington) — The most creative restaurant in the southern Berkshires, with an excellent natural wine list and locally sourced menu. $40-$60 per person.
• Red Lion Inn (Stockbridge) — The 1773 inn still serves a solid traditional American menu in the most atmospheric dining room in the Berkshires. Good for the experience as much as the food. $35-$55 per person.
• Allium (Great Barrington) — Excellent farm-to-table in a casual setting. The brunch is outstanding. $35-$50 per person.
• Bizen (Great Barrington) — Exceptional Japanese cuisine from a restaurant that sources Japanese ingredients and techniques with complete seriousness. $40-$65 per person.
• Public (Pittsfield) — The best casual restaurant in Pittsfield, with a good tap list and creative American food. Under $30.

When is the best time to visit the Berkshires?

July–August (Arts season) — Tanglewood, Jacob’s Pillow, Williamstown Theatre Festival, and Shakespeare & Company are all at full operation. Hotels book out on Tanglewood weekend evenings — reserve weeks ahead. This is the Berkshires at its most culturally alive.

October (Foliage season) — The rolling hills along Route 7 and the secondary roads through Sheffield and Monterey display some of the finest sustained fall color in Massachusetts. Peak usually arrives in mid-to-late October, about a week after the White Mountains. The cultural venues wind down but the landscape is at its most spectacular.

Avoid: The Berkshires in November and December are quiet to the point of emptiness — most cultural venues are closed, many restaurants and inns reduce hours or close for the season.

The Berkshires are best approached as a three-day minimum destination — one day for the southern Berkshires (Stockbridge, Great Barrington, Norman Rockwell Museum), one day for Lenox and Tanglewood, one day for North Adams and MASS MoCA. This gives you enough time to get into each area’s character without rushing. A Tanglewood lawn evening in late July, with the fireflies and the BSO and the smell of the summer evening, is one of New England’s genuinely great experiences. Plan your complete Berkshires and New England itinerary at the destinations guide and Plan Your Trip.