Bennington is a town in Bennington County, Vermont, United States. It is one of two shire towns of the county, the other being Manchester. As of the 2020 US Census, the population was 15,333. Bennington is the most populous town in southern Vermont, the second-largest town in Vermont and the sixth-largest municipality in the state. The town is home to the Bennington Battle Monument, which is the tallest human-made structure in the state of Vermont.