Frank Howard Building

The Old Central Fire Station is a historic fire station at 66 Allen Street in Pittsfield, Massachusetts. Built in 1895, it is the city's oldest surviving fire station, and a prominent local example of Romanesque architecture. The station was listed on the National Register of Historic Places in 1977, and was included in an expansion of Pittsfield's Park Square Historic District in 1991. It now houses offices.

The Allen Hotel is an historic hotel building in Pittsfield, Massachusetts. Built in 1915 and first operated as the Park Hotel, it is a significant local example of Renaissance Revival architecture, designed by the prominent local architect Joseph McArthur Vance. It was individually listed on the National Register of Historic Places in 1975, and included in an expansion of Pittsfield's Park Square Historic District in 1991. It no longer houses a hotel, and has been repurposed for other uses.

The Wollison–Shipton Building is a historic commercial block located at 142-156 North Street in Pittsfield, Massachusetts. Designed by architect H. Neil Wilson, it was built in 1888 when the area north of Park Square developed as a commercial and retail part of downtown Pittsfield.

The Old Town Hall is a historic building on Park Square in the heart of downtown Pittsfield, Massachusetts. This 1832 building served for 135 years as the center of municipal government. Built in the Federal style to serve as the town hall, it became City Hall when Pittsfield became a city in 1891, serving in that role until 1968. It is the city's oldest municipal building. The hall was listed on the National Register of Historic Places in 1972, and included in the Park Square Historic District in 1975.

Pittsfield is the largest city and the county seat of Berkshire County, Massachusetts, United States. It is the principal city of the Pittsfield, Massachusetts Metropolitan Statistical Area which encompasses all of Berkshire County. Pittsfield’s population was 43,927 at the 2020 census. Although its population has declined in recent decades, Pittsfield remains the third-largest municipality in Western Massachusetts, behind only Springfield and Chicopee.In 2017, the Arts Vibrancy Index compiled by the National Center for Arts Research ranked Pittsfield and Berkshire County as the number-one medium-sized community in the nation for the arts.

The Park Square Historic District is a historic district in Pittsfield, Massachusetts. The district is centered on the historic heart of Pittsfield encompassing a number city blocks adjacent to Park Square, which is at the junction of North, South, East, and West Streets. When first listed on the National Register of Historic Places in 1975, the district encompassed the park and eight buildings that faced it, including the Old Town Hall, the county courthouse, the Berkshire Athenaeum, and the First Church of Christ. In December 1991, the boundaries were expanded to the area roughly bounded by East Housatonic, South, North and Fenn Streets, and Wendell Avenue, adding 39 buildings to the district. Notable buildings included in this extension include the present City Hall (a repurposed post office building), the Berkshire Life Insurance Company Building, the Allen Hotel, the Berkshire Museum of Art and Natural History, and the Masonic temple. Pittsfield was settled in the 1740s, and was incorporated as a proprietary settlement in 1753. It was given a town charter in 1761. Park Square, the heart of the city, was laid out in 1790 on land donated by John Chandler Williams. It was located near the town's first colonial meeting house, which was erected in 1762. The square was the site of the nation's first agricultural fair, held in 1810. In the first half of the 19th century, the community began to develop industrially, principally in the area of paper manufacturing. It became a regionally important hub due to its railroad connections in the mid-19th century, and became the shire town of Berkshire County in 1868, spurring further growth. The commercial districts around the square developed in the late 19th century as a result of this growth.

The original Berkshire Athenaeum, now known as the Bowes Building, is a nineteenth century building that still stands on Park Square in Pittsfield, Massachusetts in the Berkshires. Like many New England libraries, the Berkshire Athenaeum started as a private organization. The private Public Library Association was founded in 1850. The group's name was later changed to the Berkshire Athenæum. Later still, Thomas F. Plunkett, Calvin Martin and Thomas Allen, were "instrumental in forming it into a free library". The Berkshire Athenaeum is now also known as the Pittsfield Public Library at 1 Wendell Avenue in Pittsfield, containing a collection of more than 150,000 items. The library's special collections on local history, genealogy, author Herman Melville and other local authors are some of the best in the northeast.

Samuel Harrison House is a historic house at 82 Third Street in Pittsfield, Massachusetts. Built about 1850, it was for many years home to Rev. Samuel Harrison, a regionally-prominent African-American minister (1818–1900) who served as chaplain to the 54th Massachusetts Infantry Regiment during the American Civil War. It was listed on the National Register of Historic Places in 2006.

The Berkshire Natural Resources Council (BNRC) is a non-profit land conservation and environmental advocacy organization formed in 1967 that protects and maintains more than 50 properties and 10,000 acres (4,000 ha) of conservation restrictions around the Berkshires in western Massachusetts. The mission of the BNRC is "to protect and preserve the natural beauty and ecological integrity of the Berkshires for public benefit and enjoyment."BNRC has been active in preserving natural landscapes and resources on Mount Greylock, Yokun Ridge, and the South Taconic Range. It maintains hiking trails at its Steven's Glen preserve in West Stockbridge, Basin Pond in Lee, Olivia's Lookout in Lenox, and Bob's Way in Monterey, Massachusetts. It has also been active in advocating for environmental protection and remediation of the Housatonic River watershed.

The Joseph Scelsi Intermodal Transportation Center (often referred to as the ITC or the Scelsi ITC) is a transit facility located in downtown Pittsfield, Massachusetts. The $11 million facility is named after Joseph Scelsi, a longtime State Representative who represented Pittsfield. Owned by the Berkshire Regional Transit Authority (BRTA), it is serviced by local BRTA bus services, Amtrak intercity rail service, and Peter Pan intercity bus service. The second floor of the building houses two classrooms used by Berkshire Community College and Massachusetts College of Liberal Arts.Railroad stations have been located in downtown Pittsfield since the Western Railroad opened in 1841. The original station burned in 1854; after its replacement proved inadequate, a union station was constructed in 1866 to serve the Western plus the Housatonic Railroad and the Pittsfield and North Adams Railroad. A second, larger union station replaced it in 1914. The New Haven Railroad and New York Central Railroad moved to smaller depots in 1960 and 1965, and Union Station was demolished in 1968. Rail service to Pittsfield ended in 1971 but returned in 1975 and moved to a new shelter downtown in 1981. The facility ITC opened in 2004 to combine local and intercity bus and intercity rail operations into one location.

The Berkshire Museum is a museum of art, natural history, and ancient civilization that is located in Pittsfield in Berkshire County, Massachusetts.

Berkshire Life Insurance Company Building is a historic commercial building at 5-7 North Street in Pittsfield, Massachusetts. It is located in the heart of downtown Pittsfield, facing Park Square across North Street. Built in 1868, it is one of a trio of Second Empire buildings designed by Louis Weisbsein, a Boston architect, whose style influenced later construction in the city. The building was listed on the National Register of Historic Places in 1986, and was included in an expansion of Pittsfield's Park Square Historic District in 1991.