The Shires of Vermont Byway is named for the scenic region it passes through from Vermont’s southern border with Massachusetts in Pownal, through Bennington where it intersects with the Molly Stark Byway, to Manchester where it intersects with the Stone Valley Byway in the heart of town.
This ribbon of road, Route US7 from Pownal to Bennington, and Route 7A from Bennington to Manchester, is the historic stretch that has connected the communities of the north and south shires for centuries. Nestled between the Taconic and Green Mountains and enriched by the waters of the famous Battenkill, The Shires is a popular four season destination for those seeking the authentic Vermont experience.
The Shires of Vermont Byway winds its way from south to north through the towns of Pownal, Bennington, North Bennington Village, Shaftsbury, Arlington, Sunderland, Manchester Village and Manchester Center for approximately 75 miles including side trips and five historic covered bridges. It is the same road traveled by such notables as; Green Mountain Boys leader, Ethan Allen; presidential son, Robert Lincoln; writer, Dorothy Canfield Fisher; poet, Robert Frost and illustrator, Norman Rockwell all who called this beautiful region home.