WUPE (AM)

Pittsfield Municipal Airport (IATA: PSF, ICAO: KPSF, FAA LID: PSF) is two miles west of Pittsfield, in Berkshire County, Massachusetts. The National Plan of Integrated Airport Systems for 2011–2015 categorized it as a general aviation facility.The first airline flights were Mohawk DC-3s, 1953 to 1958; Northeast DC-3s stopped at Pittsfield 1953-54 to 1962. Flights on commuter airlines like Command Airways and Precision Airlines lasted until 1983-84; Precision flew to Rutland, Vermont and New York City LaGuardia Airport.

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.

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.

Bousquet Mountain is a local ski area serving skiing and snowboarding located on a northern summit of Yokun Ridge in Pittsfield, Massachusetts within the Taconic Mountain Range. It is now owned by Mill Town Capital and shares a Summit pass with Berkshire East and Catamount Ski Area. Snowtubing is also offered with 10 lanes, 100 tubes, a magic carpet, and snowmaking on the tubing hill.

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.

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.

WBEC-FM (95.9 MHz) is a commercial station in Pittsfield, Massachusetts. It is owned by Townsquare Media and broadcasts a Top 40 radio format. WBEC-FM has an effective radiated power (ERP) of 1,000 watts. The transmitter is off Alpine Trail in Pittsfield, near South Street (U.S. Route 20).

Berkshire Community College is a public community college in Berkshire County, Massachusetts with its primary campus in Pittsfield. It also has a satellite campus in Great Barrington and classroom spaces in the city of Pittsfield. Established in the 1960s, it is the oldest college founded by the Massachusetts Community Colleges Executive Office.More than 3,000 students enroll annually in BCC's academic programs, which include associate degrees, certificate programs, and transfer programs. An additional 5,200 enroll in noncredit or workforce development courses. The majority of students are from Massachusetts, with 96% coming from Berkshire County. The student body is 61% female and nearly half of enrolled students are 23 years old or older. Berkshire Community College has been accredited by the New England Association of Schools and Colleges since 1964.

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.

The Morewood School is a historic one-room schoolhouse at 30 South Mountain Road in Pittsfield, Berkshire County, Massachusetts. Built in 1843, it was converted to a vacation cottage in the 1980s after serving for 130 years as a schoolhouse. It was listed on the National Register of Historic Places in 1984. Originally located on 4 acres (1.6 ha) around 1825, the lot has been reduced to 1 acre (0.40 ha).

The Tyringham Center School is a historic schoolhouse at 2 Church Road in Tyringham, Berkshire County, Massachusetts. Built in 1877, it is the town's only surviving 19th-century schoolhouse, and one of Berkshire County's only schoolhouses to survive from the second half of the 19th century. It was listed on the National Register of Historic Places in 2020.

South Mountain Concert Hall is a historic performance hall on New South Mountain Road in Pittsfield, Massachusetts. Founded in 1918 by Chicago native Elizabeth Sprague Coolidge, it has been home to a classical music summer performance series since then, featuring name performers including Leonard Bernstein, Rudolf Serkin, and major chamber music ensembles. The hall was listed on the National Register of Historic Places in 1973, and the extensive estate grounds are open to the public as a nature preserve.