[3] Bennington is the oldest county in Vermont still in existence, created by the first general assembly on March 17, 1778.

[4] Vermont was organized into two original counties, with Bennington in the west and Unity (a few days later renamed Cumberland) in the east.

[6] On April 13, 1781, Bennington gained the gore east of the town of Bromley (now Peru) from Windham and Windsor Counties, now known as Landgrove.

As of the 2010 United States Census, there were 37,125 people, 15,470 households, and 9,767 families living in the county.

[22] In 1828, Bennington County voted for National Republican Party candidate John Quincy Adams and for Henry Clay in 1832.

From William Henry Harrison in 1836 to Winfield Scott in 1852, the county would vote for the Whig Party's candidates.

From John C. Frémont in 1856 to Richard Nixon in 1960, the Republican Party would have a 104-year winning streak in the county.

Following the Democrats' victory in 1964, the county went back to voting for Republican candidates for another 20 year winning streak starting with Richard Nixon in 1968 and ending with George H. W. Bush in 1988, who became the last Republican presidential candidate to win the county.

The main public transportation provider in Bennington County is the Green Mountain Community Network, whose Green Mountain Express bus system has five local bus routes in and around the town of Bennington and three commuter routes to Manchester; Wilmington; Williamstown, Massachusetts; and points in between as of September 29, 2014.

There are also commuter buses to Rutland from Manchester and a regional bus line to Albany, New York from Bennington via Marble Valley Regional Transit District and Yankee Trails World Travel, respectively.

Premier Coach's Vermont Translines (a partner of Greyhound) also stops in Bennington and Manchester on its intercity bus route between Albany and Burlington.

The Shires Connector, an Amtrak Thruway intercity bus route also operated by Vermont Translines, also links Manchester and Bennington with Albany, NY's train station in Rensselaer, New York, their Greyhound bus station and airport.