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. The county was created in 1778.

Windham County is a county located in the U.S. state of Vermont. As of the 2020 census, the population was 45,905. The shire town is Newfane, and the largest municipality is the town of Brattleboro.