Visiting the Berkshires
A country of rounded hills and forests at the far western edge of Massachusetts, three hours from both Boston and New York. The great East Coast families built their "cottages" here at the end of the 19th century, and the artists followed. Today the region packs a rare density of festivals, museums and theatres into a countryside of small white villages.
The south, around Stockbridge and Great Barrington, has postcard main streets. The centre, around Lenox, lives to the rhythm of Tanglewood in summer. In the north, Williamstown and North Adams are home to two major art museums. You come for open-air music, autumn colours and gentle hikes, not for high mountains.
You will love it if
- You love classical music, dance and open-air theatre
- You want to see New England forests turn red in October
- You are after charming villages, farms and local-produce tables
Give it a miss if
- You want big peaks: the highest point is just 3,491 feet
- You are travelling without a car: the villages are scattered
- Your budget is tight: in summer and October, rooms are expensive
The must-sees
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The summer home of the Boston Symphony Orchestra, in Lenox, since 1937. You spread a blanket on the great lawn, open your picnic basket, and the music drifts over from the shed. Lawn tickets are the cheapest, and often the best.
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A former textile mill in North Adams turned into one of the largest contemporary art museums in the United States. Its vast galleries host installations that would fit nowhere else. Allow a full day: you walk for miles.
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In Stockbridge, the largest collection of the painter who told America's story in magazine covers. His studio was moved into the grounds. Afterwards, take a stroll down Main Street: it is the street in his famous Christmas painting.
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The roof of Massachusetts, at 3,491 feet, crowned by a granite tower. On a clear day you can see five states. The summit road closes in winter; the rest of the year, go up at sunset, or arrive on foot along the Appalachian Trail.
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5 Jacob's Pillow festival Festival
The oldest dance festival in the United States, hidden in the woods of Becket. From June to August, companies from around the world perform here, and the free outdoor shows take place facing the hills. Arrive early for a picnic.
The classic trap
Turning up on an October Saturday without a booking. The autumn colours draw half of New England, and the inns are full months ahead. Book in summer, or come midweek: the forests are just as beautiful, and the roads empty.
Our itineraries in the Berkshires
| Length | Itinerary | What you see |
|---|---|---|
| 2 days | Lenox › Stockbridge | Tanglewood, Rockwell, the Gilded Age mansions |
| 4 days | Great Barrington › Stockbridge › Lenox › Pittsfield | The southern villages, the music, the Shakers |
| 1 week | South to north, up to Williamstown and North Adams | The whole region, Mount Greylock and the great museums |
Start in the south, Great Barrington and Stockbridge, for the main streets and the Rockwell museum. Head up to Lenox for a concert at Tanglewood and Edith Wharton's house. Got a week? Carry on to the north, for Mass MoCA, the Clark in Williamstown and a climb up Mount Greylock.
When to visit the Berkshires
| Appeal | Season | Temperatures | The highlight | Crowds and prices |
|---|---|---|---|---|
| WinterDec. to Mar. | -10 to 2°C | Skiing and snowshoeing | Medium | |
| SpringApr. and May | 2 to 20°C | Maple syrup and waterfalls | Low | |
| SummerJune to Aug. | 14 to 27°C | Tanglewood and Jacob's Pillow | High | |
| AutumnSept. to Nov. | 2 to 20°C | The autumn colours | High |
Our advice
Come in July for the festivals, or in the first two weeks of October for the colours at their peak. September is a good compromise: Indian summer, fewer people, and the first red leaves on the heights. In April the region dozes between slush and mud; many places close.
Getting to the Berkshires
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By plane to Boston or New York The simplest
Direct flights link London with Boston and New York in seven to eight hours; from the rest of the United States, it is an easy domestic hop. Then allow about three hours' drive to Lenox or Stockbridge. Coming from abroad? Apply online for your ESTA before you leave: 40 dollars.
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By plane to Albany The closest
Albany's small airport, in New York State, is an hour from Pittsfield and Lenox. It is reached with a connection in the United States, and renting a car there is easy.
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By train to Pittsfield Car-free to start with
A daily train links Boston with Pittsfield in just under four hours, through the hills. You will still need a car once there, to reach the villages and festivals.
Rent the car at the airport: there is almost no public transport between the villages. Drive in daylight in winter, when snow falls on the hill roads, and keep an eye out for deer at dusk.
Getting around the Berkshires
A car is essential: the region stretches fifty miles from north to south along Route 7. Distances are short, half an hour between villages, but buses are rare. Park and walk the town centres, which are best explored on foot, and allow extra time on concert nights, when the roads around Tanglewood fill up.
Good to know
A UK or European driving licence is enough to rent and drive in the United States, and an International Driving Permit, cheap to get before you leave, avoids any discussion at a roadside check. On concert nights, the Tanglewood car parks empty slowly: leave before the encore if you are in a hurry, or stay and enjoy the night on the lawn.
What to eat in the Berkshires
- Farm-to-table cooking: restaurants list the names of the nearby farms that supply their vegetables and meat.
- Apple cider donuts: warm and sugary, sold at the orchards in autumn.
- Maple syrup: collected in spring at the sugar shacks, to pour over Sunday pancakes.
- Farmhouse cheeses: fresh and aged goat and cow cheeses, to taste on the region's farms.
- Craft beers: several local breweries have opened in old brick mills.
- The Tanglewood picnic: a basket of cheese, bread and wine, the tradition of summer evenings on the lawn.
To eat like the locals, stop at a roadside farm stand selling eggs, pies and vegetables on an honour system, or at a diner in Great Barrington for breakfast. Book your tables on Saturday nights in summer and October: the good places are stormed.
Where to stay in the Berkshires
| Area | What for | Good to know |
|---|---|---|
| Lenox and Lee | Tanglewood, Edith Wharton, spas | The heart of summer |
| Stockbridge | Rockwell, Naumkeag, postcard street | The most famous village |
| Great Barrington and the south | Restaurants, shops, skiing | The liveliest |
| Pittsfield | Shakers, Melville, gentle prices | The city, less charm |
| Williamstown and North Adams | Mass MoCA, the Clark, Mount Greylock | The museum north |
How much does a trip in the Berkshires cost?
| Trip | Length | Budget per person |
|---|---|---|
| Budget (motel, shared car, picnics) | 5 days | €700 to €1,000 |
| Comfort (inn, concerts, good restaurants) | 5 days | €1,400 to €2,200 |
| Luxury (spa, fine dining, best seats) | 5 days | €3,000 to €5,000 |
- Festivals: a lawn ticket at Tanglewood costs far less than a seat in the shed, and the sound is still beautiful.
- October weeks: room prices climb with the colours; a midweek stay often saves a third.
- Museums: Mass MoCA and the Clark charge admission; group them on the same day in the north.
- Minimum stays: in summer, many inns require two or three nights at weekends.
- Meals: you will eat well for less at lunchtime, and at the roadside farm stands.
Traditions and way of life in the Berkshires
The Berkshires were the countryside of America's Gilded Age rich: at the end of the 19th century, families from New York and Boston built dozens of mansions here, modestly called "cottages". Edith Wharton wrote in her house in Lenox, and Herman Melville wrote Moby-Dick in Pittsfield, facing the outline of Greylock, which reminded him of a whale.
Long before them, the Shakers, a religious community that lived by work and celibacy, had built a round stone barn at Hancock, still standing. The activist W. E. B. Du Bois was born in Great Barrington, and Norman Rockwell spent his last years in Stockbridge. Passing through in summer? Keep an evening for a show: the region has more stages than many cities.