Bennington County is a county in the U.S. state of Vermont. As of the 2020 census, the population was 37,347. The shire towns are jointly Bennington and Manchester, and the largest municipality is Bennington. Bennington is the only county in Vermont with two shire towns. Thus, it the only county in the United States to have two "shire towns" within its boundaries. The county was created in 1778.