Bennington is the oldest incorporated town in Vermont, and the area is one of the most historic parts of the state. The well-known story of Bennington's early days includes tales of the Battle of Bennington and the adventures of Ethan Allen and the Green Mountain Boys. Bennington carries the story of this community forward into the twentieth century. It pictures the town's development as a producer of textiles, paper, and a wide array of goods, including the town's famous pottery. At the same time, the area has remained a picturesque region that attracts artists, poets, and summer visitors.

Bennington explores the scenic town with more than two hundred vintage photographs from the Bennington Museum and private collections, many of which have never before been published. The area's growth and diversity are evident in views of the changing architecture, transportation, and recreational activities. Victorian estates of industrialists offset the row houses of the mid-1800s mill workers. The family horse is replaced by the trolley and then by the motor car, such as the Martin Wasp. Bennington tells a story that reveals the rich character of this historic Vermont town.