Charles Whittlesey Power House

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.

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.

Temple Anshe Amunim (Hebrew: אנשי אמונים, lit. 'Men of Faith') is a Reform Jewish congregation and synagogue located at 26 Broad Street, in Pittsfield, Berkshire County, Massachusetts, in the United States. The congregation was founded by German Jewish immigrants in 1869 as Orthodox, and adopted Reform practice in 1879. It is the second-oldest Reform congregation in the United States and its temple is the oldest synagogue building in Western Massachusetts. In 1904, Anshe Amunim joined the Union of American Hebrew Congregations. It is also affiliated with the Jewish Federation of the Berkshires.

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 Colonial Theatre is located at 111 South Street, Pittsfield, Massachusetts, in the Berkshire Mountains of western Massachusetts. Built in 1903, the theater was host to many theater greats including George M. Cohan, Sara Bernhardt, John Barrymore, Eubie Blake, Douglas Fairbanks Sr., Billie Burke, John Philip Sousa and the Ziegfeld Follies. The theater was designed by Pittsfield architect Joseph McArthur Vance along with J.B. McElfatrick. Its ornate turn-of-the 20th century interior has been well preserved by its various owners. Although the theater was closed in 1951, its grandeur had been protected through the years by George Miller and his son, Steven. Miller preserved many features of the Colonial during its conversion from a theater to the Miller's Art Supply Store, making it possible to eventually restore the theater back to its earlier grandeur, a process documented in photographer Nicholas Whitman's The Colonial Theatre: A Pittsfield Resurrection.The Colonial Theatre was named by First Lady Hillary Clinton as a National Historic Treasure in 1998. She later visited the theatre as a U.S. Senator in 2000. Following this announcement, the community invested more than $22 million to refurbish the 100-year-old Colonial Theatre, one of the only theaters of its kind from the Vaudeville age, described as "one of the finest acoustical theaters in the world." The Colonial Theatre Restoration completed work in 2006 and it is now open to the public. Many notable performers have since performed here, including James Taylor, the Lovin' Spoonful, and other musical and theater acts.

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 Berkshire Museum is a museum of art, natural history, and ancient civilization that is located in Pittsfield in Berkshire County, Massachusetts.

The Berkshire Natural Resources Council (BNRC) is a non-profit land conservation and environmental advocacy organization formed in 1967 that protects and maintains more than 50 properties and 10,000 acres (4,000 ha) of conservation restrictions around the Berkshires in western Massachusetts. The mission of the BNRC is "to protect and preserve the natural beauty and ecological integrity of the Berkshires for public benefit and enjoyment."BNRC has been active in preserving natural landscapes and resources on Mount Greylock, Yokun Ridge, and the South Taconic Range. It maintains hiking trails at its Steven's Glen preserve in West Stockbridge, Basin Pond in Lee, Olivia's Lookout in Lenox, and Bob's Way in Monterey, Massachusetts. It has also been active in advocating for environmental protection and remediation of the Housatonic River watershed.

The original Berkshire Athenaeum, now known as the Bowes Building, is a nineteenth century building that still stands on Park Square in Pittsfield, Massachusetts in the Berkshires. Like many New England libraries, the Berkshire Athenaeum started as a private organization. The private Public Library Association was founded in 1850. The group's name was later changed to the Berkshire Athenæum. Later still, Thomas F. Plunkett, Calvin Martin and Thomas Allen, were "instrumental in forming it into a free library". The Berkshire Athenaeum is now also known as the Pittsfield Public Library at 1 Wendell Avenue in Pittsfield, containing a collection of more than 150,000 items. The library's special collections on local history, genealogy, author Herman Melville and other local authors are some of the best in the northeast.

The Park Square Historic District is a historic district in Pittsfield, Massachusetts. The district is centered on the historic heart of Pittsfield encompassing a number city blocks adjacent to Park Square, which is at the junction of North, South, East, and West Streets. When first listed on the National Register of Historic Places in 1975, the district encompassed the park and eight buildings that faced it, including the Old Town Hall, the county courthouse, the Berkshire Athenaeum, and the First Church of Christ. In December 1991, the boundaries were expanded to the area roughly bounded by East Housatonic, South, North and Fenn Streets, and Wendell Avenue, adding 39 buildings to the district. Notable buildings included in this extension include the present City Hall (a repurposed post office building), the Berkshire Life Insurance Company Building, the Allen Hotel, the Berkshire Museum of Art and Natural History, and the Masonic temple. Pittsfield was settled in the 1740s, and was incorporated as a proprietary settlement in 1753. It was given a town charter in 1761. Park Square, the heart of the city, was laid out in 1790 on land donated by John Chandler Williams. It was located near the town's first colonial meeting house, which was erected in 1762. The square was the site of the nation's first agricultural fair, held in 1810. In the first half of the 19th century, the community began to develop industrially, principally in the area of paper manufacturing. It became a regionally important hub due to its railroad connections in the mid-19th century, and became the shire town of Berkshire County in 1868, spurring further growth. The commercial districts around the square developed in the late 19th century as a result of this growth.