Tanglewood
The summer home of the Boston Symphony Orchestra since 1937: orchestral weekends, chamber recitals and big-name concerts on a rolling lawn in Lenox, best enjoyed with a blanket and a picnic.
Massachusetts
The Berkshires
The Berkshires are western Massachusetts at its most generous: an orchestra playing to a picnicking lawn at Tanglewood, the largest collection of Norman Rockwell originals in Stockbridge, one of the biggest contemporary art museums in the country in a North Adams mill, an Impressionist treasure house in Williamstown, Gilded Age gardens in Lenox and the highest peak in the state above it all.
Add dance in a hillside barn, Shakespeare under the pines, waterfalls, a literary hike and a rocking-chair porch on Stockbridge Main Street, and you have a region where culture and countryside sit a few minutes apart. This guide covers the headline sights, the hotels from Lenox to Great Barrington and practical guides to seasons, itineraries and where to base yourself.
Don't miss
Tanglewood
The summer home of the Boston Symphony Orchestra since 1937: orchestral weekends, chamber recitals and big-name concerts on a rolling lawn in Lenox, best enjoyed with a blanket and a picnic.
Norman Rockwell Museum
The world's largest collection of original Norman Rockwell art, set on a hillside in Stockbridge with the painter's relocated studio, a gallery of Saturday Evening Post covers and the Four Freedoms.
MASS MoCA
One of the largest contemporary art museums in the United States, set in a former mill complex in North Adams, with enormous installations, Sol LeWitt wall drawings and a busy calendar of concerts.
Clark Art Institute
A world-class art museum in Williamstown with a famous Impressionist collection, Renoir and Degas, a landscaped campus with walking trails, and a quiet, uncrowded atmosphere.
Things to do in The Berkshires
Hand-picked: every experience here has strong traveler reviews and a verified booking link.
Norman Rockwell Museum
The world's largest collection of original Norman Rockwell art, set on a hillside in Stockbridge with the painter's relocated studio, a gallery of Saturday Evening Post covers and the Four Freedoms.
MASS MoCA
One of the largest contemporary art museums in the United States, set in a former mill complex in North Adams, with enormous installations, Sol LeWitt wall drawings and a busy calendar of concerts.
The Mount, Edith Wharton's Home
Edith Wharton's Gilded Age country estate in Lenox: a Classical Revival mansion she designed and wrote in, with formal Italian and French gardens, house tours and an evening ghost-story tradition.
Clark Art Institute
A world-class art museum in Williamstown with a famous Impressionist collection, Renoir and Degas, a landscaped campus with walking trails, and a quiet, uncrowded atmosphere.
Jacob's Pillow Dance Festival
America's longest-running international dance festival, held each summer on a Becket hillside, with ticketed performances in historic theatres and free outdoor shows on the grounds.
Naumkeag House and Gardens
A Gilded Age Shingle Style estate in Stockbridge with a landmark landscape by Fletcher Steele, including the famous Blue Steps, a birch walk and a Chinese-inspired garden.
Chesterwood, Daniel Chester French Estate
The summer home and studio of Daniel Chester French, creator of the seated Lincoln at the Lincoln Memorial, with a sculpture-filled woodland walk and gardens in Stockbridge.
Hancock Shaker Village
A living-history museum near Pittsfield on a former Shaker community, with the famous Round Stone Barn, craft demonstrations, heritage farm animals and Shaker design on 750 acres.
Mount Greylock State Reservation
The highest point in Massachusetts at 3,491 feet, with a summit war memorial tower, an auto road in season, Bascom Lodge and long views across five states from the Appalachian Trail ridge.
Berkshire Botanical Garden
A 15-acre public garden at the crossroads of Stockbridge and West Stockbridge, with display beds, a hosta collection, a herb garden, a greenhouse and a summer calendar of plant sales and festivals.
Berkshire Museum
A family-friendly museum in downtown Pittsfield that combines art, natural history and science, with an aquarium of local species, a fossil gallery and exhibits for children.
Where to stay
Hotels we would book ourselves, from splurges to good-value bases.
Wheatleigh
Lenox
A Gilded Age palazzo-style mansion on a Lenox hillside near Tanglewood, run as an intimate luxury hotel with fine dining, quiet grounds and a country-house feel.
Check rates →Cranwell Spa and Golf Resort
Lenox
A full-service resort in a Gilded Age estate in Lenox, with a golf course, spa, restaurants and grounds close to Tanglewood and the center of the village.
Check rates →The Red Lion Inn
Stockbridge
A classic New England inn on Stockbridge Main Street, with a long front porch lined with rocking chairs, antique-filled rooms and walking distance to the village and the Rockwell connection.
Check rates →The Porches Inn at MASS MoCA
North Adams
A row of restored Victorian mill-worker houses facing MASS MoCA in North Adams, with a heated pool, hot tub, and playful modern design in the northern Berkshires.
Check rates →Hotel on North
Pittsfield
A boutique hotel in the heart of downtown Pittsfield, near theatres, restaurants and the Berkshire Museum, and a handy base for central Berkshire sightseeing.
Check rates →Canyon Ranch Lenox
Lenox
A wellness resort in a historic Lenox mansion, with a large spa, fitness classes, healthy dining and programs for visitors who want a restorative Berkshires stay.
Check rates →The Williams Inn
Williamstown
A traditional inn at the center of Williamstown, steps from Spring Street and the college, and a short drive to the Clark Art Institute and MASS MoCA.
Check rates →Brook Farm Inn
Lenox
A friendly bed and breakfast in Lenox known for its poetry library, afternoon tea, home-baked breakfasts and a quiet setting a short drive from Tanglewood.
Check rates →The Briarcliff Motel
Great Barrington
A simple, budget-friendly motel on the Route 7 corridor in Great Barrington, close to the town's restaurants, Monument Mountain and the southern Berkshires.
Check rates →Tour + stay
Ready-made pairings: a top sight and a hotel that suits it. Add both to your trip and book each when you are ready.
Do
TanglewoodStay
WheatleighLenox
Do
Norman Rockwell MuseumStay
The Red Lion InnStockbridge
Do
MASS MoCAStay
The Porches Inn at MASS MoCANorth Adams
The Berkshires guides
The Berkshires for First-Timers: What to See, Where to Base Yourself and How It All Fits Together
A practical first-visit guide to the Berkshires: how the towns fit together, the headline sights, how to plan around Tanglewood and the foliage, and which hotels suit which trip.
The Berkshires in Three Days: Music, Museums, Gardens and a Mountain View
A three-day Berkshires itinerary that sequences Stockbridge, Lenox and the northern Berkshires with a minimum of driving, with rainy-day swaps and timing tips.
Where to Stay in the Berkshires: Lenox, Stockbridge, North Adams, Pittsfield and Great Barrington Compared
A guide to choosing a base in the Berkshires, comparing the main towns by atmosphere, price and distance to the sights, with hotel ideas for each.
Summer in the Berkshires: Tanglewood, Jacob's Pillow, Shakespeare and Company and More
How to plan a Berkshires summer of music, dance and theatre, with advice on tickets, picnics, timing and combining festivals in a single trip.
The Best Time to Visit the Berkshires: Seasons, Foliage, Festivals and Winter Calm
A season-by-season guide to visiting the Berkshires, covering summer festivals, October foliage, winter sports, spring mud and how crowds and prices change.
The Berkshires Art Trail: Rockwell, MASS MoCA, the Clark and the Gilded Age Estates
How to plan an art-focused Berkshires trip, linking the Rockwell Museum, MASS MoCA, the Clark and the historic estates, with tips on timing and pacing.
