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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.

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.

WBEC (1420 kHz) is a commercial AM radio station broadcasting a talk and sports radio format. It is licensed to Pittsfield, Massachusetts, and is owned by Townsquare Media.WBEC is powered at 1,000 watts. By day, it uses a non-directional antenna. But at night, to protect other stations on 1420 AM, it uses a directional antenna with a two-tower array. Programming is also heard on FM translator W230CP at 93.9 MHz.

WBRK-FM (101.7 MHz, "Star 101.7") is a commercial FM radio station in Pittsfield, Massachusetts. It is owned by WBRK, Inc. and broadcasts a hot adult contemporary radio format.

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.

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.

The Eaton, Crane & Pike Company Factory, once the Terry Clock Company Factory is a historic former factory complex in Pittsfield, Massachusetts. Developed over a period of years between 1883 and 1967, the complex was home to one of Pittsfield's major paper concerns, and a significant local employer. Now converted to mixed residential and light industrial use, it was listed on the National Register of Historic Places in 1990.

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.

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.

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.

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.