Upper North Street Commercial District

Saint Joseph Central High School was a private, college preparatory, Roman Catholic high school in Pittsfield, Massachusetts. Saint Joseph offered a co-educational intensive college preparatory curriculum to students in grades 9 through 12. SJCHS had a strong international student community with students from Korea, China, Austria, and Spain, but did not offer boarding facilities. International students live with local host families. Former principal Francis X. Foley announced his resignation in June 2013, and has been replaced with Dr. Amy Gelinas. The School closed in June 2017.

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.

Holy Family Parish, designated for Polish immigrants in Pittsfield, Massachusetts, United States, was founded in 1912. It is one of the Polish-American Roman Catholic parishes in New England in the Diocese of Springfield in Massachusetts. The parish closed in 2008.

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.

Barrington Stage Company (BSC) is a regional theatre company in the Berkshires of Western Massachusetts. It was co-founded in 1995 by Artistic Director Julianne Boyd, and former Managing Director Susan Sperber in Sheffield, Massachusetts. In 2004, BSC developed, workshopped, and premiered the hit musical The 25th Annual Putnam County Spelling Bee. Following the successful Broadway run, which nabbed two Tony Awards for Best Book and Best Featured Actor, BSC made the move to a more permanent home in Pittsfield, Massachusetts. The company which was previously housed in the Consolati Performing Arts Center at Mount Everett High School in Sheffield, Massachusetts, purchased and renovated the Berkshire Music Hall in downtown in 2005. The venue was renamed the Boyd-Quinson Mainstage after its renovation. The 520-seat Mainstage Theatre is now located at 30 Union Street. In 2012 the company purchased an old VFW building on Linden Street in Pittsfield, turning it into the Sydelle and Lee Blatt Performing Arts Center . The Blatt Center includes the St. Germain Stage (formerly known as Stage 2) and a 99-seat space dubbed Mr. Finn's Cabaret. Additionally, the company acquired the Wolfson Theater Center which serves as the company's administrative offices and a rehearsal space in the center of Pittsfield today. BSC's scenic departments operate out of a 22,100 square-foot facility, located at 34 Laurel Street, referred to as the Production Center (PC). The PC was purchased in 2019 in order to more conveniently construct and pre-assemble scenic elements before being loaded into BSC's performance spaces. Before purchasing the PC, BSC operated out of a warehouse at Fenn and Fourth streets in order to construct their sets.

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 Frank Howard Building is a commercial building at 124–132 Fenn Street and 67–71 Federal Street in Pittsfield, Massachusetts. The 1916 Classical Revival building was designed by Joseph McArthur Vance, a prominent local architect, and is the best preserved of his works. It was listed on the National Register of Historic Places in 2012.

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.

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 Old Central High School is a historic school building at 99 2nd Street in Pittsfield, Massachusetts. Built in 1898, it is one of the most architecturally elaborate school buildings in the city. The building was listed on the National Register of Historic Places in 1980. It is now residential housing.

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 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.