Why Go to The Berkshires
YOUR DESTINATION AT A GLANCE
The Berkshires are New England countryside at its most inviting. This rural region of western Massachusetts, about 140 miles from New York City and roughly 120 miles from Boston, is full of winding roads, rolling mountains, farmland and charming small towns, making it a favorite escape for city dwellers.
Outdoor lovers come year-round for hiking, skiing, climbing and zip-lining in the mountains, plus paddleboarding, kayaking and fishing on the region's lakes. The Berkshires are also a cultural treasure. Visit the Norman Rockwell Museum in Stockbridge, the world-class contemporary art at MASS MoCA, and The Mount, Edith Wharton's elegant estate. In summer, enjoy outdoor concerts at Tanglewood, the summer home of the Boston Symphony Orchestra, and the dance at Jacob's Pillow.
Browse antique shops and cozy cafes in towns like Lenox, Great Barrington and Stockbridge, enjoy farm-to-table dining, and pick berries and apples at local orchards in season. Fall foliage here is spectacular. I'll find a charming inn or resort and plan a relaxing getaway around the seasons and events you love.
BEST FOR
Arts enthusiasts, hikers, couples and foliage seekers
BEST MONTHS
May–October
EXPLORE
Lenox is near Tanglewood; Stockbridge has a classic village center; Great Barrington offers shops and restaurants, and Williamstown is home to renowned museums.
SIX18 SIGNATURE DESTINATION GUIDE
The Berkshires
North America › Northeast › USA › Massachusetts
Wooded hills, celebrated arts and charming New England villages
Mountain & Alpine
Art
Culture
Autumn
SIX18 INSIDER TIP
Choose one northern and one southern Berkshires day rather than repeatedly driving the entire region.
Experiences Worth Exploring
THINGS TO DO
Check concert dates, ticket rules and lawn policies in advance.
Tanglewood
The Boston Symphony Orchestra’s celebrated summer music venue is set among lawns near Lenox.
Allow time for the grounds and changing exhibitions.
Norman Rockwell Museum
See the artist’s work and explore exhibitions in a scenic Stockbridge setting.
Budget several hours; gallery installations vary.
MASS MoCA
A major contemporary art museum occupies a sprawling former industrial complex in North Adams.
Check summit-road seasons and weather before heading up.
Mount Greylock State Reservation
Explore mountain landscapes around Massachusetts’ highest peak.
Pair a museum visit with a walk outdoors when weather permits.
The Clark Art Institute
Visit art galleries and landscaped grounds in Williamstown.
A wellness-focused resort in a historic estate setting, with a structured approach to spa, fitness and relaxation.
Canyon Ranch Lenox
Lenox
Hotel Tags
An adults-oriented wellness resort with guided experiences and a peaceful Berkshire setting.
Miraval Berkshires Resort & Spa
Lenox
Hotel Tags
A landmark historic inn near the village center and the Norman Rockwell Museum.
The Red Lion Inn
Stockbridge
Hotel Tags
An intimate luxury country-house hotel overlooking landscaped grounds near Tanglewood.
Wheatleigh
Lenox
Hotel Tags
A contemporary inn within walking distance of Williams College and local art museums.
The Williams Inn
Williamstown
Hotel Tags
Curated Accommodations
WHERE TO STAY
November in The Berkshires
High 46°F · Low 30°F · Rain 4 in
Quiet fall days, cozy inns and Norman Rockwell Museum visits.
Late spring through autumn suits hiking and cultural outings; summer is festival season and fall brings foliage.
Best Times to Visit The Berkshires
WHEN TO GO
06
Tanglewood and seasonal event parking
Build extra flexibility around tanglewood and seasonal event parking when visiting The Berkshires. Verify access, cancellations, road or sea conditions and the return journey before committing to an excursion.
05
Village center and estate trails
Plan time for village center and estate trails in The Berkshires. Check terrain, weather, accessibility and local restrictions; allow an alternate transfer where walking is impractical.
04
Rental cars for dispersed towns
For more flexible journeys, rental cars for dispersed towns may be relevant in The Berkshires. Use authorized providers, confirm the pickup location and agree on payment arrangements before travel.
03
Limited regional bus connections
Consider limited regional bus connections when organizing trips beyond your accommodation. Confirm the exact boarding location, advance booking requirements and any transfer between terminals.
02
Amtrak service in the region
For travel within The Berkshires, investigate amtrak service in the region. Verify route coverage, ticket rules, operating dates and the last return service before relying on it for sightseeing.
01
Albany and regional airports
Albany International Airport (ALB) is about an hour from much of the Berkshires, and Bradley International (BDL) near Hartford is a similar drive from the southern towns. A car is essential.
Driving is the easiest way to connect villages and trailheads. Check seasonal event calendars and reserve popular performances early.
Getting Around The Berkshires