The Appalachian Trail passes through the southern Berkshires within easy reach of Great Barrington. Several access points within a short drive of town provide entry to the trail, which here runs through mature hardwood forest, across open ridge lines, and past excellent viewpoints.
The most popular section for day hikers from Great Barrington is the stretch to Jug End, which offers panoramic views across the Housatonic Valley and into Connecticut. Race Brook Trail, about 8 kilometres south of town off Route 41, leads to a series of waterfalls and on to open ridgeline views. The full AT through the southern Berkshires covers about 90 kilometres of Massachusetts before crossing into Connecticut.