Holden–Leonard Mill Complex

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 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 Bennington Museum is an accredited museum with notable collections of art and regional history. It is located at 75 Main Street, Bennington, Vermont, USA. The museum's history dates to 1852 when the Bennington Historical Association was first incorporated. In 1923 the association acquired a former church, which it renovated and opened to the public in 1928 as the Bennington Historical Museum. The building was subsequently expanded in 1938, 1960, 1974, and 1999. In 1938 its name was revised to the Bennington Historical Museum and Art Gallery to reflect its holdings of artwork, and in 1954 it was renamed the Bennington Museum. The collections have a special focus on Vermont and adjacent areas of New York and Massachusetts. In 1972 the schoolhouse attended by Grandma Moses was moved to the grounds and included as part of the museum. It also includes a genealogy and history research library. Key aspects of the museum's permanent collections include: Grandma Moses Gallery - the largest public collection of paintings by noted local artist "Grandma Moses", Anna Mary Robertson Moses (1860-1961). Fine Art Gallery - including works by Ralph Earl, Oliver Tarbell Eddy, Erastus Salisbury Field, Ammi Phillips, William Morris Hunt, Frederick MacMonnies, Rockwell Kent, and Simon Moselsio. Bennington Modernism - avant-garde artworks from the early 1950s through the mid-1970s by artists including Pat Adams, Willard Boepple, Anthony Caro, Paul Feeley, Helen Frankenthaler, Patricia Johanson, Vincent Longo, Kenneth Noland, Jules Olitski, Dan Shapiro, David Smith, and Tony Smith. Gilded Age Vermont - focused on Bennington from the mid 1800s to mid 1900s. Exhibits include paintings by William Morris Hunt, Frederick MacMonnies’ portrait painting of May Suydam Palmer, and glass and metal works by Lewis Comfort Tiffany, as well as a parlor organ manufactured by the Estey Organ Company and the Martin Wasp, a luxury automobile made in Bennington in 1924-25. Military Gallery - focusing on the Revolutionary War's Battle of Bennington, and including an exhibit of Vermont-made firearms from 1760 to 1900. Bennington Pottery - featuring pieces by Norton Pottery (1785-1894), United States Pottery Company (1847-1858), Fenton pottery, and redware. Textile Gallery - the Bennington flag, one of the oldest “stars and stripes” in existence, a Green Mountain Boys flag belonging to John Stark, the Jane Stickle Quilt, and other textiles.The museum also displays temporary exhibits on a wide variety of subjects.

Bennington is a town in Bennington County, Vermont, United States. It is one of two shire towns (county seats) of the county, the other being Manchester. As of the 2020 US Census, the population was 15,333. Bennington is the most populous town in southern Vermont, the second-largest town in Vermont (after Colchester) and the sixth-largest municipality in the state. The town is home to the Bennington Battle Monument, which is the tallest human-made structure in the state of Vermont. The town has a long history of manufacturing, primarily within wood processing. The town is also recognized nationally for its pottery, iron, and textiles.

The Downtown Bennington Historic District encompasses the historic commercial heart of Bennington, Vermont. Centered on the junction of Main, South, and North Streets, it exhibits a variety of commercial architectural styles from the early 19th to mid-20th century. It was listed on the National Register of Historic Places in 1980, and was enlarged in 2008.

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 First Congregational Church of Bennington, also known as the Old First Church, is a historic church in Old Bennington, Vermont. The congregation was organized in 1762 and the current meeting house was built in 1805. The building, one of the state's best examples of Federal period religious architecture, was added to the National Register of Historic Places in 1973.

Old Bennington is a village in Bennington County, Vermont, United States. It is located entirely within the town of Bennington. As of the 2020 census, the village had a population of 156.The village and its surrounding area were added to the National Register of Historic Places in 1984 as Old Bennington Historic District. It is roughly bounded by the former Rutland railroad bed, Monument Avenue, West Road, Seminary Lane, Elm Street, and Fairview Street. The district is noted for its well-preserved Revolutionary War-era homes, and is significant as one of the earliest settlements in Vermont. The centerpieces of the district are the Old First Church (built in 1806 and restored in 1937) and the Bennington Battle Monument.

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 Catamount Tavern was a tavern in Old Bennington, Vermont, United States. Originally known as Fay's House, it is marked now by a granite and copper statue placed in 1896. It was built 1769 and burned in 1871. During the tavern's 102 years of existence, it was the site of many important events in Vermont's colonial and revolutionary history. It was, for instance, the site of the public hanging of New York grantee and member of the Queen's Rangers, David Redding. Arrested for horse-theft, he managed to escape while being transported to Albany, New York. But he was re-arrested very soon and taken to Bennington, where, after a trial in the tavern, he was sentenced to be hanged in a field adjacent to the tavern. A local merchant, John Burnham, delayed the execution by pointing out that Redding had been tried by six rather than twelve men. Colonel Ethan Allen advised the crowd depart to return the day fixed for the execution in the act of the governor and council, adding with an oath, and according to Dr. John Spargo who wrote a book on the hanging which can be found in the Bennington Museum library, "you shall see somebody hung, for if Redding is not hung, I will be hung myself." Upon this assurance, the uproar ceased and the crowd dispersed. Redding was sentenced to hang on June 11, 1778 and his bones, after many years of being used for research and being kept in a drawer, were laid to rest 200 years later in the Old First Church Cemetery. The name Catamount Tavern came about when Settlers from Bennington Vermont posted a stuffed catamount on the tavern's signpost to repel the New Yorkers who claimed their land. The Catamount served as headquarters for the Green Mountain Boys while making their plans against the New Yorkers and the British. Ethan Allen planned the capture of Fort Ticonderoga here; John Stark planned British General Burgoyne's defeat here, eventually leading to the Battle of Bennington. The Catamount was also the meeting place of Vermont's only form of government then, in 1775, the Vermont Council of Safety.

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.