Arrowhead (Herman Melville House)

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.

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.

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.

Canoe Meadows Wildlife Sanctuary is a 253-acre (1.02 km2) wildlife sanctuary located in Pittsfield, Massachusetts. The sanctuary, managed by the Massachusetts Audubon Society, is flanked by the Housatonic River on its southwestern border and contains hiking trails suitable for birdwatching, observing other wildlife, and scenic viewing. The sanctuary also contains a 4.5-acre (1.8 ha) community garden, from which local residents may rent garden plots measuring 300 square feet (28 m2).

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.

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.

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.

Pittsfield High School is a four year comprehensive public high school in Pittsfield, Massachusetts, United States. It serves the city of Pittsfield. The school dates its founding to 1844. It is administered by the Pittsfield Public Schools district and is the oldest of the district's two high schools. Enrollment for the 2014-2015 school year included 916 students. 51% of the student population was female and 49% were male. Students of African American, Asian, Hispanic, Native American, Native Hawaiian, Pacific Islander and Multi-Race, Non-Hispanic ethnicity and heritage comprised 21.8% percent of the student population.

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

Providence Court, previously St. Luke's Hospital, is a historic former hospital building at 379 East Street in Pittsfield, Massachusetts. The Colonial Revival building was constructed in 1926, and was the first Roman Catholic hospital in Berkshire County. St. Luke's merged with Pittsfield General Hospital in 1967 to form Berkshire Medical Center, in the nation's first mergers between religious and non-sectarian hospitals. The building was converted into elderly housing in 1978–1981. It was listed on the National Register of Historic Places in 1987.