Beware the common misconceptions about identifying Western Massachusetts. The first is that Western Mass. is synonymous with the Berkshires or the Berkshire Mountains. Not true. “The Berkshires” generally refers to rolling hills in the southern and southwestern area of Massachusetts.
The other is that it begins only west of Springfield, which rests along the Interstate 91 corridor from Connecticut to Vermont, so the distinction doesn’t matter much anyway.
All you really need to know is that Western Mass. encompasses everything that lies west of that I-91 corridor, and that there are many ways to get there.
From east or west: I-90, or the Massachusetts Turnpike, is faster and more direct, though there are tolls (but, crucially, no toll plazas anymore since the state switched to all-electronic tolling in 2016). You can avoid tolls and take the scenic route on U.S. 20, but it will be a slower slog with twists and turns. State highways 2 and 9 cross Western Mass. in an area that the faster roads simply don’t service. They are generally very scenic too.
From north or south: If you’re coming from the north or south, you have the choice of I-91 or U.S. 7, with I-91 offering speed and U.S. 7 offering scenery and a toll-free ride.
This is going to be your cheapest option. There are Greyhound stops all over western Mass. coming from Boston and from outside of Massachusetts, including in Amherst, Deerfield, Great Barrington, Lee, Stockbridge, and Williamstown.
Peter Pan buses also roll through the region from various points, including to Great Barrington, North Adams, and Pittsfield.
There are actually a few options, all of which will require another mode of transportation (most likely a car) after the flight: The Worcester Regional Airport in Worcester, about 30 minutes west of Boston; Boston-Logan International itself, which is about a two-hour drive from Western Mass.; Bradley International Airport in Windsor Locks, Connecticut, about 25 minutes south of Springfield; and Albany International Airport, about one and a half hours west of the Massachusetts line.
Ticket prices vary, of course, depending on carrier and destination. The best bets for flight deals likely require flying into Boston or Albany, simply because they’re bigger and serve the most airlines.
While this is the most scenic option, it’s also the most cumbersome. Amtrak’s Lake Shore Limited departs daily from Boston’s South Station and stops at Springfield and Pittsfield in Western Mass. on its way to Chicago. But the ride from Boston to Springfield alone can take two-plus hours.
There is also Amtrak’s Adirondack from New York to Montreal, which stops in Hudson, New York, and in Albany; from there, a visitor could travel via car or bus to Western Mass. The route along the Hudson River to Albany is absolutely gorgeous.
Amtrak’s Vermonter offers a similar scenic experience. That route from Washington, D.C., to St. Albans, Vermont, stops in Springfield, Holyoke, Northampton, and Greenfield, on the eastern edge of Western Mass.