High Quality Content by WIKIPEDIA articles! Bennington is a town in Bennington County, Vermont, United States. It is one of two shire towns (county seats) of the county, the other being Manchester. The population was 15,764 at the 2010 census. By population, Bennington is the largest town in southern Vermont, the third-largest town in Vermont (after Essex and Colchester), and the sixth-largest municipality in the state (after Burlington, Essex, Rutland, Colchester, and South Burlington). Bennington is home to the Bennington Battle Monument, which is the tallest structure in the state of Vermont.