Hebert Arboretum

Berkshire Medical Center is a private, non-profit 302-bed community teaching hospital in Pittsfield, Massachusetts affiliated with the University of Massachusetts Medical School.

The A. H. Rice Silk Mill is a historic textile mill in Pittsfield, Massachusetts. Built in 1876 to house a woolen mill, this multi-section brick building was purchased in 1887 by William Bainbridge Rice, who established his silk-processing operation here. The premises were expanded in 1895 after Rice acquired a New Jersey silkworks and moved its equipment here. The Rice Company was one of Pittsfield's largest business at the turn of the 20th century. It produced a number of highly specialized materials, including silk cords for parachutes, which they later also made out of nylon. The company was particularly known for its braided silk cord. The facilities were used in the production of silk cording until 2006. The property has since been converted residential use.The mill complex is located northeast of downtown Pittsfield, in the city's Morningside residential neighborhood. It is on 3 acres (1.2 ha), bounded on the north by Burbank Street, the east by Spring Street, and the west by Cherry Street. It consists of five interconnected brick mill buildings, erected between 1876 and 1947, all of which are between two and three stories in height. All exemplify the use of an insurance standard fireproof design, with brick exterior walls, and heavy timber frames inside. Windows are typically set in segmented-arch openings with quarry-faced granite sills. As part of the residential conversion, some ground-floor window bays have been converted into entrances.The mill was listed on the National Register of Historic Places in 2015.

Springside Park is a recreational city park on the north side of Pittsfield, Massachusetts. At 237.5 acres (96.1 ha) it is the city's largest park. Much of the park is wooded, providing for passive recreational opportunities such as hiking. The southwestern section of the park, nearest to North Street, is developed, with ballfields, a bath house, pond, and Springside House, an Italianate mansion whose early construction dates to c. 1856. Some of the parklands are also used for the Hebert Arboretum. Through the 1960s the City of Pittsfield operated a ski rope tow and provided ski lessons at the park. The park was listed on the National Register of Historic Places in 2008.

Wahconah Park is a city-owned baseball park located in Pittsfield, Massachusetts and nestled in a working-class neighborhood. One of the last remaining ballparks in the United States with a wooden grandstand, it was constructed in 1919 and seats 4,500. Through the park's history, 201 different Pittsfield players went on to the Major Leagues, and 100 different Pittsfield players already had some Major League experience. The park was listed on the National Register of Historic Places in 2005.In the July 23, 1990, issue of Sports Illustrated, author Daniel Okrent raved about the park in his column entitled Just A Little Bit of Heaven – Pittsfield's Wahconah Park is Baseball as it Oughta Be.In 2012, the stadium became the home field of the Pittsfield Suns, an expansion franchise of the Futures Collegiate Baseball League.

Pilgrim Memorial Church and Parish House is an historic church and parsonage at 249 Wahconah Street in Pittsfield, Massachusetts. The church was designed by H. Neill Wilson, and was completed in 1897. It is a good local example of Gothic and Romanesque architecture, and was the first church built to serve the mill workers in the city's north end. The property was listed on the National Register of Historic Places in 2005. The present church congregation is Presbyterian.

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.

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.

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 Upper North Street Commercial District is a historic district on the north side of downtown Pittsfield, Massachusetts, United States. Representing an expansion of Pittsfield's historic downtown area northward from Park Square in the late 19th century, the district encompasses primarily commercial buildings fronting on North Street between Columbus and Madison Avenues on the west side, and between Eagle and Maplewood Avenues on the east side. The notable exceptions are the Berkshire Eagle building, located on Eagle Street next to Sottile Park, and the St. Joseph's Church complex. The district features Colonial Revival and Renaissance style architecture. It was added to the National Register of Historic Places in 2002.

Silver Lake is a lake in Pittsfield, Massachusetts that has had environmental concerns and been subject to a clean-up effort by both the city of Pittsfield and the EPA.

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.

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.