The Boston Symphony Orchestra has spent its summers at Tanglewood since 1937. The Koussevitzky Music Shed seats around 5,000 people under a roof; the lawn behind it takes perhaps 10,000 more, and a lawn ticket costs a fraction of a seat. People arrive with blankets, folding tables, candles and full dinners, and the orchestra plays Mahler to a hillside of picnickers as the light goes.
It is the oldest arrangement of its kind in America and it is the reason the Berkshires have the cultural density they do. Jacob's Pillow, the dance festival, is nine miles away and has run since 1933. Shakespeare & Company, the Berkshire Theatre Group and Barrington Stage all work in the same few valleys.
The factory
MASS MoCA occupies twenty-six buildings of the former Sprague Electric works at North Adams — a complex that at its peak employed four thousand people making capacitors, including components for the Manhattan Project and later the Gemini programme. Sprague closed in 1985 and took the town's economy with it.
The museum opened in 1999 across about 250,000 square feet and is now the largest contemporary art space in the United States. The scale is the point: works that no conventional museum can house, including a Sol LeWitt wall drawing retrospective installed across three floors and scheduled to remain on view until 2033.
The valleys
Lenox and Stockbridge, in the south, hold Tanglewood, the Norman Rockwell Museum and the Gilded Age estates — the Berkshires were a summer colony for New York and Boston money before Newport took over.
North Adams and Williamstown, in the north, have MASS MoCA and the Clark Art Institute, which holds a major Impressionist collection in a rural setting that makes no sense until you learn it was sited there partly out of Cold War fear of a nuclear strike on a city.
Great Barrington and the south county have the restaurants and the smaller towns.
The eight below are grouped that way.
Lenox and Stockbridge
Tanglewood and the estates.
Wheatleigh occupies an 1893 house modelled on a Florentine palazzo, built by a Vanderbilt granddaughter as a wedding present, in twenty-two acres landscaped by Frederick Law Olmsted, with nineteen rooms and Tanglewood across the fields. It is the best hotel in New England's interior.
Wheatleigh
Lenox · 5★ · $$$$
An 1893 palazzo copy in an Olmsted landscape, nineteen rooms
Check availabilityBlantyre sits on 110 acres in a 1902 Tudor-style mansion with formal gardens, a spa and a dining room of considerable formality.
Blantyre
Lenox · 5★ · $$$$
A 1902 Tudor mansion on 110 acres with formal gardens
Canyon Ranch Lenox occupies a former Gilded Age estate as an all-inclusive wellness property with fitness, hiking and medical programmes.
Canyon Ranch Lenox
Lenox · 5★ · $$$$
A Gilded Age estate run as an inclusive wellness programme
Miraval Berkshires sits nearby as a second wellness resort with an adults-only policy, a large spa and a programme-led rate.
Miraval Berkshires
Lenox · 5★ · $$$$
Adults-only with a large spa and a programme rate
Check availabilityThe Red Lion Inn occupies a 1773 inn on the Stockbridge main street, the subject of a Norman Rockwell painting, with a porch and rocking chairs facing the road.
Kemble Inn sits in a Lenox mansion with a small room count, a garden and a short drive to Tanglewood.
North Adams and the north
MASS MoCA and the Clark.
Tourists occupies a reworked 1960s motor lodge across the river from MASS MoCA, with a suspension footbridge to a wooded trail and a shop selling records and flannel.
Tourists
North Adams · 4★ · $$$
A reworked motor lodge with a footbridge to the woods
Check availabilityPittsfield
The centre.
Hotel on North sits on the Pittsfield main street in a restored building with a good restaurant and the best value in the county.
Hotel on North
Pittsfield · 4★ · $$
A restored main street building at the county's best value
Check availabilityWhat we have left off
The inns and bed and breakfasts across the Berkshire towns are excluded, and there are a great many in nineteenth-century houses. They are guest houses rather than hotels.
What to do
Buy a lawn ticket for Tanglewood and bring a proper picnic. It is the correct way to do it and the locals will out-cater you regardless.
Give MASS MoCA half a day. The Sol LeWitt building alone takes an hour and the scale of the Turrell and Kusama installations does not reproduce.
See the Clark, then walk the trails behind it — the institute owns 140 acres and the hilltop pasture above the galleries is part of the experience.
Visit The Mount, Edith Wharton's house at Lenox, which she designed herself according to the principles in her own book on decoration.
Drive the Mohawk Trail in October, and accept that everyone else has had the same idea.
Practical notes
Albany is an hour away, Boston and New York around two and a half. A car is essential.
The summer season runs late June to early September and Tanglewood weekends fill the county. October is foliage and books equally far ahead. Winter is quiet with skiing at Butternut and Jiminy Peak.
Book Tanglewood and the restaurants before the hotel on a festival weekend.
Every hotel bookable in the Berkshires
What is a lawn ticket?
Admission to the grass behind the Tanglewood shed, at a fraction of a seat price, where people bring dinner and listen to the orchestra outdoors.
What is MASS MoCA?
Twenty-six buildings of a former electronics factory converted into the largest contemporary art space in the United States.
Lenox or North Adams?
Lenox for Tanglewood and the estates, North Adams for the art and much lower prices. Forty-five minutes apart.
How many nights?
Three. One for music, one for art and one for the towns.
