Downtown Bennington Historic District

The Old Bennington Post Office is a historic government building at 118 South Street in Bennington, Vermont, United States. Also known at one time as the U.S. Federal Building, it is a Greek Revival building built in 1914, and now houses the Bennington Police Department. It was listed on the National Register of Historic Places in 1976 for its architecture.

The Ritchie Block is a historic commercial building at 465-473 Main Street in downtown Bennington, Vermont. Built in 1895-96, it is a high quality example of Classical Revival architecture, with a distinctive pressed metal entablature. The building was listed on the National Register of Historic Places in 1986.

Bennington station is a historic former railroad depot at 150 Depot Street in downtown Bennington, Vermont. Built in 1897-98 by the Bennington and Rutland Railroad, it is the only Richardsonian Romanesque railroad station in the state of Vermont. It was listed on the National Register of Historic Places in 1988 as Bennington Railroad Station, and since then housed a restaurant, which closed in 2018. It now is an office space for MSK Engineering and Design and Goldstone Architecture.

The Julius and Sophia Norton House is a historic house at 300 Pleasant Street in Bennington, Vermont. Its main block, completed in 1846, is one of the state's finest examples of Greek Revival architecture. It was listed on the National Register of Historic Places in 2021.

The Pratt-McDaniels-LaFlamme House is a historic house at 501-507 South Street in Bennington, Vermont. Built about 1800, this Federal period building encapsulates the changing residential trends in the town over a 200-year historic, starting as a farm house, then that as a businessman, and eventually subdivided into worker housing. It was listed on the National Register of Historic Places in 2002.

The School Street Duplexes are a pair of historic two-family worker houses at 343-345 and 347-349 School Street in Bennington, Vermont. Built about 1916, they are well-preserved examples of typical worker housing units of the 1910s. They were listed on the National Register of Historic Places in 2007.

The Frederick Squire House is a historic house at 185 North Street in Bennington, Vermont. Built about 1887, it is one of the town's finest examples of Queen Anne Victorian architecture. It was listed on the National Register of Historic Places in 1992.

The Holden–Leonard Workers Housing Historic District encompasses a collection of mill-related tenement houses, plus a former mill store, in Bennington, Vermont. They are located on Benmont and Holden Avenues, near the former Holden–Leonard Mill Complex, Bennington's largest employer in the late 19th century. The district was listed on the National Register of Historic Places in 2011.

Bennington is a census-designated place (CDP) in Bennington County, Vermont, United States. It is located entirely within the town of Bennington. The population of the CDP was 9,074 at the 2010 census, or 57.6% of the population of the entire town.

The Former Bennington High School is a historic school building at 650 Main Street in Bennington, Vermont. Built in 1913 and enlarged several times, it is architecturally significant as an excellent example of Beaux-Arts architecture, and is historically important for its role in local education. The building, closed in 2004, was listed on the National Register of Historic Places in 2005. Bennington's high school educational services are now provided by Mount Anthony Union High School.

The Holden–Leonard Mill Complex, also known colloquially as the Big Mill and now as Vermont Mill Properties, is a historic industrial complex at 160 Benmont Avenue in Bennington, Vermont. Built of many parts between about 1865 and 1925, it is one of the largest and most architecturally distinctive 19th-century mill complexes in the state, and was a major regional employer for many years. Now redeveloped into a variety of commercial and industrial uses, it was listed on the National Register of Historic Places in 1988.

Mount Anthony Union High School is the public high school serving Bennington, Vermont, as well as the towns of Shaftsbury, Woodford, and Pownal, Glastenbury, and Bennington County. As of the 2023-2024 academic year, the school has about 1,200 students enrolled in grades 9-12 and has a faculty of nearly 130.It is easily accessible from US Route 7, VT Route 279, and the Green Mountain Express Red Line bus. Mount Anthony is the third-largest school in the state of Vermont. The average graduation rate is eighty-five percent. The school yearbook is officially known as the Patriot Ledger, and the school newsletter is called Mount Anthony Connections. Additionally, the school runs a bi-weekly sports newsletter, The Patriot Press, which reports on the school's athletic teams. The sports teams in their athletic program are collectively known as the Patriots. Led by head coach Brian Coon, the Patriots wrestling team holds the national record for most consecutive state titles won as of 2023 (34). Under the guidance of 1st year head coaches Frank Gaudette and Corey Greene, MT. Anthony won their 34th consecutive title, which is the longest current state championship streak in the country including all high school sports.The Mount Anthony Football team is also very successful being state champion runner-ups in the 1986–1987, 1992–1993 and 2021-2022 season and state champions in the 1974-1975, 1994–1995 and 2022-2023 seasons. The Patriots won the state championship in Division II by defeating Bellows Falls in double overtime. As of 11/6/2021 they play in Division II in the state of Vermont. They host home games at Spinelli Field. The Southwest Tech campus is housed on the school's campus.