The trail proceeds northward through the Housatonic River valley and hills to its west, veering northwesterly and, at Salisbury, ascending the southern Taconic mountains, at Lion's Head affording a view northeasterly towards Mt. Greylock and other points in Massachusetts, and at Bear Mountain, reaching over 2000 feet in elevation for the first time since Pennsylvania and yielding views across the Hudson River valley to the Catskills and across the broad expanse of the Housatonic valley and the Berkshire and Litchfield Hills to the east.