Bernardston lies along the path of Interstate 91 and U.S. Route 5, both of which pass from Greenfield through town towards the Vermont state line. Bernardston is the northernmost town along both I-91 and U.S. 5 in Massachusetts, which then both cross into Vermont. Massachusetts Route 10 leaves its concurrency with Route 5 in the southern part of town, before passing eastward towards the Connecticut River and New Hampshire. The town also lies along the north-south portion of the Springfield Terminal railway, which roughly follows the path of Route 10. The nearest regional bus service is in Greenfield, with the nearest general aviation airport in Montague. The nearest Amtrak station is in Greenfield, and the nearest national air service is at Bradley International Airport in Windsor Locks, Connecticut.