The land in this area rises in elevation from the Connecticut Valley to heights of over 2,000 feet above sea level. Twenty to thirty miles wide in Massachusetts, the Western New England Upland is home to the Berkshire Hills and Mount Greylock, the highest point in Massachusetts at 3,487 feet above sea level.he land in this area rises in elevation from the Connecticut Valley to heights of over 2,000 feet above sea level. Twenty to thirty miles wide in Massachusetts, the Western New England Upland is home to the Berkshire Hills and Mount Greylock, the highest point in Massachusetts at 3,487 feet above sea level.