WBEC-FM

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.

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.

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.

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.

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.

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.

Pleasant Valley Wildlife Sanctuary is a 1,405 acres (569 ha) wildlife sanctuary located in Lenox, Massachusetts owned by the Massachusetts Audubon Society. There are 7 miles of trails and a large pond on Yokun Brook. The Overbrook Trail leads to the summit of Lenox Mountain (2126 feet).Pleasant Valley has an outdoor summer day camp, seasonal special events, and year-round educational programs for preschoolers to adults.

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.

Arrowhead, also known as the Herman Melville House, is a historic house museum in Pittsfield, Massachusetts. It was the home of American author Herman Melville during his most productive years, 1850–1863. Here, Melville wrote some of his major works: the novels Moby-Dick, Pierre (dedicated to nearby Mount Greylock), The Confidence-Man, and Israel Potter; The Piazza Tales (a short story collection named for Arrowhead's porch); and magazine stories such as "I and My Chimney". The house, located at 780 Holmes Road in Pittsfield, was built in the 1780s as a farmhouse and inn. It was adjacent to a property owned by Melville's uncle Thomas, where Melville had developed an attachment to the area through repeated visits. He purchased the property in 1850 with borrowed money and spent the next twelve years farming and writing there. Financial considerations prompted his family's return to New York City in 1863, and Melville sold the property to his brother. The house remained in private hands until 1975, when the Berkshire County Historical Society acquired the house and a portion of the original 160-acre (65 ha) property. The Society restored most of the house to Melville's period and operates it as a house museum; it is open to the public during warmer months. It has been designated a National Historic Landmark and is listed on the National Register of Historic Places.

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.

Miss Hall's School is an independent school for grades 9-12 located in Pittsfield, Massachusetts. Founded in 1898 by Mira Hinsdale Hall, a graduate of Smith College, it was one of the first girls' boarding schools established in New England. It is recognized internationally for its experiential leadership curriculum, service and internship programs, and inclusive global community.