Frelinghuysen Morris House and Studio

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.

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 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.

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 Windsor Mountain School was a private, co-ed boarding school for grades 9 through 12 located in Lenox, Massachusetts.

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).

Elm Court is a former Vanderbilt mansion located on Old Stockbridge Road, straddling the town line between Lenox and Stockbridge, Massachusetts. It is listed on the National Register of Historic Places and until July 2012 was owned and operated as a hotel by descendants of the original owners. Elm Court was built as the Berkshire summer home of William Douglas Sloane and Emily Thorn Vanderbilt, a member of the wealthy American Vanderbilt family. Designed by premier architectural firm Peabody and Stearns, with gardens and landscape design by Frederick Law Olmsted, Elm Court is the largest Shingle style house in the United States, with 106 rooms.

Shakespeare & Company is an American theatre company and venue complex located in Lenox, Massachusetts, in the Berkshires region of western Massachusetts. It was founded in 1978 by artistic director Tina Packer. The company performs plays by Shakespeare and new plays of "social and political significance", reaching over 75,000 patrons annually. It also conducts training programs for professional classical actors as well as education programs for elementary through high school students, the latter reaching over 50,000 students annually.

Lenox is a town in Berkshire County, Massachusetts, United States. The town is in Western Massachusetts and part of the Pittsfield Metropolitan Statistical Area. The population was 5,095 at the 2020 census. Lenox is the site of Shakespeare & Company and Tanglewood, summer home of the Boston Symphony Orchestra. Lenox includes the villages of New Lenox and Lenoxdale, and is a tourist destination during the summer.

Lenox School was an Episcopal independent, college-preparatory boarding school for boys in grades nine through twelve in Lenox, Massachusetts, in the United States.

Spring Lawn is an historic home on Kemble Street in Lenox, Massachusetts. Built in 1904 for John Alexandre, the mansion is considered a unique blend of Beaux-Arts and Classical Revival styles. Spring Lawn was designed by Guy Lowell who was also the architect of the Museum of Fine Arts, Boston and the New York Supreme Court courthouse. The property has seen many uses over the years, including acting as the home of the National Music Foundation and Shakespeare & Company. Today, there are plans to convert the mansion and its surrounding property into a luxury resort.

The Lenox Library is the principal public library of Lenox, Massachusetts. It is managed by the non-profit Lenox Library Association, founded in 1856, and is located at 18 Main Street, in a former county courthouse that is listed on the National Register of Historic Places.