Bennington is a town located in Bennington County in the southwestern part of Vermont. It has a population of approximately 15,800 and a median household income of approximately $40,000. Neighboring towns include Pownal, Shaftsbury, Wilmington, and Woodford. Bennington has 3 elementary schools. It shares its middle school with neighboring towns in 7th and 8th grade. It is part of the Mount Anthony Union High School. It is probably best known for being the namesake for the Battle of Bennington, which is still celebrated as a holiday in many towns in Vermont. Browse available Bennington VT real estate below.