The Shires of Vermont is a point-to-point race from Bennington to Manchester Center, Vermont. The course follows mainly secondary roads through the villages of North Bennington, Shaftsbury, and Arlington, the campus of Bennington College, and rural countryside.
The course has a net elevation loss of 160 feet; however, the course is challenging with lots of rolling hills.
Approximately eight miles of the course consists of hard-packed dirt.