Berkshires and Pioneer Valley are easy to visit by car
Auto Routes to the The Berkshires and Pioneer Valley
From Boston and points north and east, I-90 will take travelers through central Massachusetts and into the southern part of the region, including Springfield, Chicopee, Great Barrington, Stockbridge, and Lenox.
For a more northerly, scenic, and historic route, Massachusetts Route 2, from Boston, heads west across the top of the state, ending at Williamstown, near the Vermont and New York border. The 60 miles of the route between Orange and Williamstown is known as the Mohawk Trail, following a legendary Indian trail and passing some of the most scenic territory in the state.
From New Hampshire, Vermont and points due north, travelers should take I-91 south. The route passes through Greenfield, Amherst, Holyoke, Northampton, and Springfield before continuing on into Connecticut. I-90, Route 9 and Route 2 all intersect with I-91, allowing for travel further west.
From upstate New York and points west, I-90 travels to Western Massachusetts, passing near Great Barrington and Springfield. Further north, Massachusetts State Route 9 crosses the NY border near New Lebanon, NY, and goes through Pittsfield, finally meeting up with I-91 just outside of Northampton.
From Connecticut, Rhode Island, New York City, and points south and west, take I-95 to I-91 north (at New Haven). For a more westerly Route north, take CT Route 8, or U.S. Route 7 north from I-95. U.S. Route 7 runs directly through Great Barrington and Stockbridge, and continues north through Pittsfield.