With verdant landscapes and breathtaking views, the Berkshires trips follow the winding Appalachian Trail in the scenic Massachusetts countryside. Many trips will hike to the top of Mt. Greylock, which towers over the surrounding area at 3,491 ft, and admire the pristine forest and charming New England towns from the highest peak in Massachusetts.

This area is of medium difficulty, there are many ridges and peaks that offer great views, but it can be challenging. For more information on the AT in the Berkshires, please visit the Appalachian Mountain Club of the Berkshires.