The town was first settled in 1761 by four families from Hardwick and two from Amherst, Massachusetts.
First of the New Hampshire Grants, Bennington was chartered on January 3, 1749, by Colonial Governor Benning Wentworth and named in his honor.
It was granted to William Williams and 61 others, mostly from Portsmouth, New Hampshire.
The town has ready access to natural resources and waterpower, and a long history of manufacturing, primarily within wood processing.
The town is also recognized nationally for its pottery, iron, and textiles.
The average household size was 2.29 and the average family size was 2.88. For every 100 females age 18 and over, there were 82.6 males.
In the town, the population was spread out with 23.5% under the age of 18, 10.7% from 18 to 24, 26.1% from 25 to 44, 22.0% from 45 to 64, and 17.8% who were 65 years of age or older. The median income for a household in the town was ,765, and the median income for a family was ,489. Four representatives from Bennington's two voting districts currently represent the town in Montpelier.Abundant sunshine, along with heavy showers and thunderstorms, are frequent during the summer months. July is typically the wettest month, and February is the driest.Although tornadoes seldomly occur there, an F2 tornado did hit North Bennington on May 31, 1998 during an extremely rare tornado outbreak in the region. Bennington averages 60.77 inches (154 cm) of snow annually.).One such storm dumped very wet, heavy snow on October 4, 1987, catching many residents off guard because it occurred quite early in that year's fall season.The storm resulted in many downed trees and power lines, due in part to that year's fall foliage still being intact.Due to its location in the southernmost portion of Vermont, it is geographically closer to the capital cities of Albany, Hartford, and Concord than it is to its own state capital, Montpelier.