Pittsfield Municipal Airport (Massachusetts)

WUPE (1110 kHz) is a commercial AM radio station in Pittsfield, Massachusetts. It is owned by Townsquare Media and it simulcasts the classic hits format of 100.1 WUPE-FM. WUPE serves the Berkshire Mountains area. The station is a daytimer and must sign off the air at sunset, according to Federal Communications Commission rules. By day, WUPE transmits with 5,000 watts, using a directional antenna, but because 1110 AM is a clear channel frequency reserved for KFAB Omaha and WBT Charlotte, WUPE must be off the air at night, when radio waves travel further. Programming is also heard in Pittsfield on FM translator W277CJ at 103.3 MHz. That gives listeners three spots on the dial to hear WUPE, AM 1110, FM 100.1 and FM 103.3.

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.

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).

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.

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.

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.

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.

The Nichols–Sterner House is a historic house at 428 Swamp Road in Richmond, Massachusetts. Built about 1820, it is one of only two brick houses built in a Federalist-Greek Revival transition style in Richmond. It was listed on the National Register of Historic Places in 1987.

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.

The Charles Whittlesey Power House is a historic house located at 575 South Street in Pittsfield, Massachusetts. Built about 1912, this Tudor Revival house and its landscaped setting are a rare local example of the country house style propounded by the English architect Edwin Lutyens. The house was built for Charles Whittlesey Power, a local businessman who also served one term as mayor of Pittsfield. It was listed on the National Register of Historic Places on August 8, 1997.

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.