Bennington is a town in Bennington County, Vermont, United States. It is one of two shire towns of the county, the other being Manchester. The population was 15,737 at the 2000 census. By population, Bennington is the largest town in southern Vermont, the third-largest town in Vermont, and the sixth-largest municipality in the state. Bennington is home to the Bennington Battle Monument, which is the tallest structure in the state of Vermont.