Destinations / The Berkshires
The Berkshires Travel Guide
Western Massachusetts hills with more culture per square mile than anywhere else in New England. I plan it as two halves: Lenox, Stockbridge and Great Barrington in the south for inns, Tanglewood and dinners, and Williamstown and North Adams up north for the Clark and MASS MoCA. You need a car, and summer and foliage weekends book up months out.
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Where I'm sending people now
Lenox for Tanglewood and the wellness resorts, Stockbridge or Great Barrington for small-town charm, and North Adams or Williamstown for museums.
Late June to early September for Tanglewood and summer theater, and late September to mid-October for foliage. Winter is quiet and cheaper, good for spa resorts and skiing, but several sites close or go weekends-only.
Wellness resorts are all-inclusive and pricey: Canyon Ranch starts around $1,125 per person a night and Miraval runs about $1,700 to $2,500 a night for two plus a service charge. The best inns run about $200 to $450 a night, more on Tanglewood and foliage weekends, plus roughly 11 to 12% room tax.
Two famous Lenox hotels are not taking guests as of November 2026: Wheatleigh stopped hotel operations in spring 2024 and is for sale, and Blantyre has been closed since late 2021 with no reopening date. The Mount Greylock summit road closed for the season on October 30 and reopens in mid-May.
Where I'm sending people now
Hawaii
Maui, Kauai, Oahu and the Big Island, and how to pick between them.
Italy
Rome and the Amalfi Coast, with the hotels and tours worth booking ahead.
Caribbean
Punta Cana, Turks and Caicos and Puerto Rico, all-inclusive and not.
Where I'm sending people now
Hawaii
Maui, Kauai, Oahu and the Big Island, and how to pick between them.
Italy
Rome and the Amalfi Coast, with the hotels and tours worth booking ahead.
Caribbean
Punta Cana, Turks and Caicos and Puerto Rico, all-inclusive and not.
Know before you go
Getting there
Most people drive: about 3 hours from New York City and 2.5 hours from Boston, with Albany International Airport about an hour from Lenox and Bradley in Hartford about 1.5 hours. International visitors usually fly into JFK, Newark or Boston Logan and rent a car, and Amtrak reaches Pittsfield on the daily Lake Shore Limited plus the summer-only Berkshire Flyer from New York.
Getting around
Rent a car. The towns are 15 to 45 minutes apart, local buses are sparse, and taxis and rideshares are thin, especially after dinner, so I only skip the car for a stay that never leaves Canyon Ranch or Miraval.
Money and tipping
Massachusetts charges a 5.7% state room tax plus a local tax of up to 6%, Miraval adds a service charge on cash rates, and Canyon Ranch and Miraval include meals, so compare them against an inn plus dinners out. To save, go midweek or in winter and early spring, when inn rates drop and minimum stays mostly disappear.
How I'd spend 3 days
Day 1 Arrive in Lenox, walk the village, then dinner at Alta or Bistro Zinc.
Day 2 Norman Rockwell Museum in the morning, The Mount after lunch, Tanglewood on the lawn in summer.
Day 3 Drive north to the Clark and MASS MoCA, with lunch in Williamstown.
Tip Book Tanglewood and Saturday dinners when you book the hotel; summer weekends sell out.
Hotels I'd book in the Berkshires
Things to do in the Berkshires
Where to eat in the Berkshires
Alta Restaurant & Wine Bar
Bistro Zinc
Once Upon a Table
The Red Lion Inn Main Dining Room
Prairie Whale
Number Ten
Mezze Bistro + Bar
RARE 297
Where I'm sending people now
Hawaii
Maui, Kauai, Oahu and the Big Island, and how to pick between them.
Italy
Rome and the Amalfi Coast, with the hotels and tours worth booking ahead.
Caribbean
Punta Cana, Turks and Caicos and Puerto Rico, all-inclusive and not.
The Berkshires FAQ
How far are the Berkshires from New York City and Boston?
Lenox is about 150 miles from Manhattan, roughly 3 hours by car, and Great Barrington is closer to 2.5 hours. From Boston it's about 2.5 hours west on the Mass Pike. Friday afternoon traffic in summer and foliage season can add an hour either way.
What is the best town to stay in the Berkshires?
Lenox is my top pick for a first trip: it's closest to Tanglewood, has the wellness resorts and is walkable for dinner. Stockbridge is the most classic village, Great Barrington has the best restaurant scene, and North Adams or Williamstown make sense if museums are the priority.
When is peak fall foliage in the Berkshires?
Color usually starts at higher elevations like Mount Greylock in late September and peaks in the valleys around the first two weeks of October. Columbus Day weekend is the busiest weekend of the year, so book hotels several months ahead or aim for midweek.
When is the Tanglewood season?
Tanglewood runs from late June to early September; the 2026 season ran June 21 to September 2. The 2027 lineup is usually announced in winter, and popular-artist shows and summer Saturdays sell out fast, so book tickets and hotels together.
Is the Berkshires worth visiting in winter?
Yes, if you want quiet, cozy inns, spa time and skiing at Jiminy Peak, Butternut or Bousquet, usually from late November or December to early April. Canyon Ranch, Miraval, the Clark and MASS MoCA stay open, but the Mount Greylock summit road and Hancock Shaker Village close, and The Mount is weekends-only until January 2.
Can you visit the Berkshires without a car?
It's possible but limiting. Amtrak's Berkshire Flyer runs from New York to Pittsfield on summer weekends (June 12 to September 13 in 2026), the daily Lake Shore Limited connects Boston and Albany with Pittsfield, and Peter Pan buses run from New York. Once you're there, taxis are scarce, so car-free works best at an all-inclusive like Canyon Ranch or Miraval.
What is the closest airport to the Berkshires?
Albany International Airport is the closest major airport, about an hour from Lenox and Pittsfield. Bradley International near Hartford is about 1.5 hours away, and international visitors usually fly into New York or Boston and drive about 3 hours.