The town is home to the Bennington Battle Monument, which is the tallest human-made structure in the state of Vermont.

First of the New Hampshire Grants, Bennington was chartered on January 3, 1749, by Colonial Governor Benning Wentworth and named in his honor.

Of these, Old Bennington is the original settlement, dating back to 1761, when Congregational Separatists arrived from Connecticut and from Amherst and Hardwick, Massachusetts.

Although the battle took place approximately 12 miles (19 km) to the west in what is now the state of New York, an ammunition storage building located in Bennington was an important strategic target.

German reinforcements under the command of Lt. Col. Heinrich von Breymann looked set to reverse the outcome, but were prevented by the arrival of Seth Warner's Green Mountain Boys, the Vermont militia founded by Ethan Allen.

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.

Its largest for-profit manufacturing employer is NSK Steering Systems America, Inc., with a workforce of 864 as of March 2013.

[24] Saint Gobain owns a plastic factory, the former ChemFab plant, which has contaminated the environment with Perfluoroalkyl and Polyfluoroalkyl Substances (PFAS).

Low interest loans, site-ready properties for manufacturing, R&D, Retail, and Technology are a few of the benefits available to new and existing industries.

Long time ski clothing company, CB Sports was headquartered in Bennington.

They operated a popular factory outlet store in town which closed in 2008, due to slow sales as a result of the Great Recession.

Bennington has a historic downtown with businesses that include a chocolatier, bakery, cafes, pizza parlors, Chinese restaurant, live theatre, breweries and distilleries, bookshop, men's and women's clothiers, jewelers, Vermont crafts and products, toy stores, antique stores, music shops, a hobby shop, a country store, an art shop, a museum, and several galleries.

[26] The downtown area is noted for its historically preserved architecture, outdoor seasonal dining, locally owned shops, cafés, Memorial Fountain Park, antique shops, and river walk paralleling the Walloomsac River.

In January 2005, the Select Board proposed a big box bylaw, primarily in response to Wal-Mart's plans to raze its existing 51,000-square-foot (4,700 m2) outlet and replace it with a 150,000-square-foot (14,000 m2) Supercenter.

Continuing education is supported by a diverse mix of colleges and career development centers.

[32] Bennington is home to the 35-time defending state wrestling champion Mount Anthony Patriots.

They are: U.S. Route 7, originating in Connecticut and continuing northward to the Canada–US border, enters Bennington from the town of Pownal.

This road forms a rough semi-circle shape around and north of the center of the town, loosely paralleling VT Route 9 while doing so.

Intercity bus service is provided by the weekday operating Yankee Trails World Travel's Albany-Bennington Shuttle,[37] as well as by Premier Coach's Vermont Translines, in its partnership with Greyhound, which operates its Albany to Burlington bus line daily.

[40] Also referred to as "Southwest Vermont's Airport", it sits near the northern flank of Mount Anthony and close to the Bennington Battle Monument.

The town also runs a recreation center on Gage Street, which contains a large indoor year-round swimming pool, softball fields, outdoor basketball court and weight room.

[42] Bennington also has a small network of mostly disconnected multi-use recreational trails; there are plans to better connect these paths in the future.

Bennington is the former home of the Chamber Music Conference and Composers' Forum of the East, a summer institute for amateur musicians.

The Symphony plays a challenging program of the traditional repertoire as well as commissioning a new work each year.

VAE hosts exhibitions, artist and community workspaces, and the Basement Music Series.

In addition to the Albany television stations, which include WRGB (CBS), WTEN (ABC), WNYT (NBC), WXXA-TV (Fox) and WMHT (PBS), Comcast carries WCAX-TV, the Burlington CBS affiliate, and Rutland Vermont PBS outlet WVER.

The radio stations WBTN-AM 1370 and VPR affiliate WBTN-FM 94.3 broadcast from, and are licensed to Bennington.

[52] Non-purchased surface and groundwater is supplied by the Bolles Brook in Woodford and the Morgan Spring in Bennington, respectively.

Comcast and Consolidated Communications also provide the town with landline phone and high speed Internet service.