U.S. Route 7 passes through the center of town, and was once part of New England Interstate Route 4 (also known as the New York-Berkshire-Burlington Way). Massachusetts Route 23 passes from west to east through town, combining with Massachusetts Route 41 and U.S. Route 7 in the western part of town and Massachusetts Route 183 in the eastern part of town, which also follows part of the path of Route 7 northward from Route 23 before splitting towards the village of Housatonic. Great Barrington is approximately south of Exit 2 of Interstate 90 (the Massachusetts Turnpike), the nearest interstate highway.