Stockbridge Bowl

Shadow Brook Farm Historic District is located in Stockbridge, Massachusetts. It is a historic district that includes six re-purposed farm buildings related to the former 'Shadowbrook' mansion destroyed by fire in 1956. Designed by architect H. Neill Wilson with landscaping by Frederick Law Olmsted, the mansion and farm buildings were built for Anson Phelps Stokes in 1893. Andrew Carnegie acquired Shadowbrook in 1917 and died there in 1919. It served as a Jesuit novitiate from 1922 until 1970. Following the fire, a non-equivalent structure of the same name took its place and currently is home to the Kripalu Center. Today the historic district primarily encompasses Berkshire Country Day School, which acquired its campus from the Stokes family in 1963. The historic district was added to the National Register of Historic Places in 1988.

Tanglewood is a music venue and festival in the towns of Lenox and Stockbridge in the Berkshire Hills of western Massachusetts. It has been the summer home of the Boston Symphony Orchestra since 1937. Tanglewood is also home to three music schools: the Tanglewood Music Center, Tanglewood Learning Center, and the Boston University Tanglewood Institute. Besides classical music, Tanglewood hosts the Festival of Contemporary Music, jazz and popular artists, concerts, and frequent appearances by James Taylor, John Williams, and the Boston Pops Orchestra.

The Tanglewood Music Festival is a music festival held every summer on the Tanglewood estate in Stockbridge and Lenox in the Berkshire Hills in western Massachusetts.The festival consists of a series of concerts, including symphonic music, chamber music, choral music, musical theater, contemporary music, jazz, and pop music. The Boston Symphony Orchestra is in residence at the festival, but many of the concerts are put on by other groups. It is one of the premier music festivals in the United States and one of the top in the world.

The Kripalu Center for Yoga & Health is a nonprofit organization that operates a health and yoga retreat in Stockbridge, Massachusetts. Its 160,000-square-foot (15,000 m2) facility is a former Jesuit novitiate and juniorate seminary built in 1957.

The Tanglewood Jazz Festival was a summer music festival, featuring contemporary jazz artists. In 2012, the event was cancelled. It was held every year on Friday, Saturday, and Sunday of Labor Day weekend, in Lenox, Massachusetts. The festival was held since the early 1990s, at Tanglewood, which is a beautiful outdoor festival grounds, and the summer home of the Boston Symphony Orchestra during June, July, and August, and given over to the jazz festival on the final weekend of the season. Friday night's concert by tradition featured Latin jazz music. Saturday afternoon usually featured pianist Marian McPartland and her guest, and also another concert as well. Saturday night usually featured the contemporary greats and is held in the main venue, known as the "shed". Sunday featured two concerts, one in the afternoon, and on in the evening, often featuring Dave Brubeck. Artists who appeared include Miles Davis, Diana Krall, Wynton Marsalis, Natalie Cole, Ahmad Jamal, Donal Fox, Nancy Wilson, Roy Haynes, Roy Hargrove, Jimmy Smith, Freddie Hubbard, Ray Charles, Hiromi Uehara, and many more. The festival is world-renowned and famous for its contributions to jazz culture.

The DeSisto School were a pair of therapeutic boarding schools founded by Michael DeSisto, DeSisto at Stockbridge School in Massachusetts (from 1978 to 2004) and the DeSisto at Howey School in Florida (1980 to 1988). It closed in 2004 amid allegations by state authorities that the school endangered the health and safety of its students.

Stockbridge School was a progressive co-educational boarding school for adolescents near the Interlaken section of Stockbridge, Massachusetts and which operated from 1948 to 1976.

The Tanglewood Music Center is an annual summer music academy in Lenox, Massachusetts, United States, in which emerging professional musicians participate in performances, master classes and workshops. The center operates as a part of the Tanglewood Music Festival, an outdoor concert series and the summer home of the Boston Symphony Orchestra (BSO).

Wheatleigh is a historic country estate on West Hawthorne Road in Stockbridge, Massachusetts, United States. Built in 1893 to a design by Peabody and Stearns, it is one of the few surviving great Berkshire Cottages of the late 19th century, with grounds landscaped by Frederick Law Olmsted. Its estate now reduced to 22 acres (8.9 ha), Wheatleigh was listed on the National Register of Historic Places in 1982. It is now operated as a hotel.

The Frelinghuysen Morris House and Studio is a historic house museum and former art studio in Lenox and Stockbridge, Massachusetts. The house and studio were home to American Abstract Artists George L.K. Morris and Suzy Frelinghuysen. The studio was built in Bauhaus style in 1930 by Morris and his friend George Sanderson. The house was added in 1941, designed by John Butler Swann. The house and studio were entered onto the National Register of Historic Places in 2016.The house contains furnishings and decorations unchanged since the couple's lifetime. The art collection includes cubist frescoes and paintings by Morris and Frelinghuysen, as well as works by Pablo Picasso, Juan Gris, Georges Braque, Joan Miró and Henri Matisse.

Yokun Ridge consisting mainly of West Stockbridge Mountain and the Lenox Mountain massif, is a ten-mile stretch of the Taconic Mountains south of Pittfield, Mass. The term was invented in 1971 by a conservation group to draw attention to a perceived geographical continuity. The name was accepted in 2009 by the United States Board on Geographic Names. The area is notable for its recreational and scenic value, as well as its conserved land and proximity to the tourist attractions of Lenox and Stockbridge. Yokun Ridge is in West Stockbridge, Stockbridge, Lenox, Richmond, and Pittsfield, Massachusetts. Approximately one-third of the zone is protected as open space reserve, municipal watershed, and wildlife sanctuary.

Citizens Hall is a historic municipal building at 13 Willard Hill Road in Interlaken, a village of Stockbridge, Massachusetts. Built in 1870 as a schoolhouse and community meeting center, it is a well-preserved local example of Second Empire architecture. The hall was listed on the National Register of Historic Places in 1972, and included as a contributing property in the Old Curtisville Historic District in 1976. It now houses Berkshire Art Center (IS183, INC).