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Onota Lake is located in Pittsfield, Massachusetts. It is 617 acres (2.50 km2) in area, located entirely in the City of Pittsfield and is owned by it. It is divided into north and south basins due to the old roadway that marked to north end with minimal water exchange between them and empties via Onota Brook which flows southeast into the West Branch of the Housatonic River in Pittsfield. The "cottagers" of the late 19th century and early 20th century built large summer mansions along its shores. Onota Lake is popular for fishing, swimming, water skiing, jet skiing, and sailing. It is home to the famous Pittsfield event "Live on the Lake", a summer concert series consisting of local bands. Camp Winadu is located along its shores. The Williams Ephs men's and women's crews row on the lake.

Pittsfield Cemetery is a historic cemetery at 203 Wahconah Street in Pittsfield, Massachusetts. Established in 1850, it is good example of a rural cemetery, and is the resting ground of many prominent Pittsfield residents, with a number of architecturally significant elements. It also houses a number of Pittsfield's earliest burials, which were relocated here from a cemetery near the city center. The cemetery was listed on the National Register of Historic Places in 2007.

Taconic Vocational High School is a vocational high school in Pittsfield, Massachusetts, United States. Taconic was built in 1968 and opened in 1969, which serves as a high school of choice for students in Pittsfield. The school's primary focus is on vocational training and it offers such courses as auto mechanics, printing, drafting, electronics, carpentry, and others. In May 2016, J. H. Maxymillian Inc. broke ground on a $120.8 million plan to construct a new Taconic High School at the same location. The new building was completed in time for the start of the 2018 school year and the old school was demolished upon completion of the new one. An expanded parking lot and soccer field were built where the old school stood in 2019. The new building covers 246,520 square feet. Along with Pittsfield High School, it is one of two high schools in the Pittsfield Public School system. In March 2022, the Taconic Braves were renamed as the Thunder.

WRRS-LP (104.3 FM) is a radio station licensed to Pittsfield, Massachusetts, United States. The station serves the Pittsfield area and is currently a program of United Cerebral Palsy of Berkshire County.

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.

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.

Hillcrest Hospital is a 77-bed general hospital located at 165 Tor Court, Pittsfield, Massachusetts. It was founded in 1908 by Dr. Charles Harper Richardson, who saw the need for a surgical hospital in the community. This was the 2nd hospital in Pittsfield at the time.Hillcrest moved to its current location in 1951. In 1996 Hillcrest Hospital merged with Berkshire Medical Center, and is now (2021) the Hillcrest Campus of BMC.

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.

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.

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 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.