The Berkshires feel like New England’s escape valve. Rolling hills, world-class arts (Tanglewood, MASS MoCA, Jacob’s Pillow), charming villages, and some of the best fall color in Massachusetts. Lenox and Stockbridge are the anchors.
Berkshires
Plan a Trip to Berkshires →Scroll
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Region
massachusetts
Best Time
Jun, Jul, Aug +2 more
Daily Budget
$55–$400 USD
Getting There
Drive from Boston (2.5 hours via Mass Pike). Drive from NYC (2.5 hours via Taconic Parkway). Peter Pan bus to Pittsfield or Lee.
Before You Go: Travel Insurance
Unexpected injuries on mountain trails or winter roads can lead to costly medical bills. We recommend SafetyWing for every trip — it's affordable, covers medical and evacuation, and you can sign up even after you've left home.
"We've thankfully never had to file a claim, but having it is peace of mind every time we board that plane." — Scott
Check SafetyWing Rates →Affiliate link — we earn a commission at no extra cost to you. Full disclosure.