Ski Butternut

Eagleton School was a residential treatment facility located in Great Barrington, Massachusetts for boys ages 9–22 who have a variety of emotional and behavioral problems. It was privately owned by Bruce Bona. It was the host of the Great Barrington Christmas party.

Kutsher's Sports Academy (KSA) is a summer sleepaway camp in Monterey, Massachusetts, for children ages 7–17. It was originally "conceived and developed by Milton and Joseph Kutsher and legendary basketball coach Clair F. Bee in 1968." The land was originally the Harmony Country Club. The Kutsher family owned and operated the academy until 2005 when they sold the camp to Marc White, the longtime Executive Director. Until 2007 it was located in Monticello, New York. The camp moved to the Berkshires at the start of 2008, and is now located on Lake Buel, just outside Great Barrington, Massachusetts. The former site in Monticello is being leased by an Orthodox Jewish camp.Part of the reason for the move may be because the site was considered for a casino before the deal between the Kutsher family and the St. Regis Mohawks was cancelled in favor of another site.Campers choose from a variety of sports, tailored to their own interests, either to increase their skills in a particular sport(s) or to try a sport they have not tried before. There are also opportunities for campers to play sports on a purely recreational level. Ten of the camp’s coaches have been there for more than 20 years. In 2007, Wil Cordero spent the whole summer there as a coach and has stayed with KSA ever since; other famous athletes have come to participate in a clinic for a day. Creative and performing arts activities were available as well. Mike Gilberg, a former camper and baseball coach, took over as Director of Kutsher's Sports Academy in 2016. As seen in the Times-Herald Record on December 26, 2007, the Sullivan County site was leased to a Satmar group for five years beginning in 2008. The reputation was so stellar among athletes that Joe DiMaggio and Wilt Chamberlain trained here in the off season. Wilt Chamberlain and Kareem Abdul Jabbar (then Lew Alcindor) faced each other for the first time in the Maurice Stokes Game, which was held each summer at the KSA Field House.

Camp Half Moon is a co-ed sleepover camp on Lake Buel in Monterey, Massachusetts. Camp Half Moon was established as a boys camp in 1922. The Mann family, originally from Lititz, Pennsylvania, currently own and operate Half Moon and purchased it from Dr. Ed Storey in 1967, who had owned and operated it for over 25 years. "Doc" Storey had been a history teacher in Pelham, New York, and many campers during the 1950s and 1960s came from Pelham and surrounding communities of southern Westchester County. For many years a large number of the boys attending Half Moon came not only from the northeastern United States but also from all across Latin America. Within just a few years after the 1959 Cuban Revolution numerous families who escaped from the Communist takeover of the island and resettled in Puerto Rico were sending their sons to Half Moon to have a broader experience with American youngsters from the mainland. The camp is now for both boys and girls.

Lake Buel is a 196-acre (0.79 km2) great pond in Berkshire County, Massachusetts just south of Route 57 and east of Great Barrington. It is surrounded by over one-hundred summer homes and a few dozen year-round homes in about a dozen separate, tight-knit neighborhoods, each with its own private or semi-private road. The roads do not interlink.The lake is named after Samuel C. Buel of Tyringham, Massachusetts who saved people from drowning on the lake (called at the time Six Mile Pond) on July 23, 1812.The northern shore of the lake is in the town of Monterey and the southern shore is in New Marlborough. There is a paved boat ramp on the northwest shore owned by the Public Access Board and managed by Forests and Parks and Fisheries and Game. A portion of the Appalachian Trail crosses over a breached mill dam along the northern inlet.

Searles High School was a public high school located in Great Barrington in the Berkshire Hills of western Massachusetts. Students attended the school from Great Barrington, the villages of Housatonic, Van Deusenville and other communities in the southern Berkshire region. Searles High School was founded in 1898 and closed in 1968, when its students transferred to a new regional high school.

The Wheeler Family Farmstead is a historic farm complex at 817 South Main Street in Great Barrington, Massachusetts. The farmhouse has elements dating to the 1730s, including evidence of building methods used by Dutch settlers of the Hudson River valley, and has been successively modified in each of the following centuries, with the last significant work occurring in the 1920s. All of the surviving farm buildings in the complex are at least 90 years old, and some date to the 19th century. The property was listed on the National Register of Historic Places in 2011, and is now the museum and headquarters of the Great Barrington Historical Society.

WSBS (860 kHz) is a commercial AM radio station in Great Barrington, Massachusetts. It is owned by Townsquare Media and has a full service adult contemporary radio format, mixed with local news, talk and sports. World and national news is supplied by ABC News Radio. WSBS is an affiliate of the Boston Red Sox Radio Network.

The Searles Castle is a French chateau-style castle-style house in Great Barrington, Massachusetts. Built in the 1880s, the romantically imagined structure has seven stories and includes a "dungeon" basement. The castle was initially designed by Stanford White of McKim, Mead and White, a famous New York architectural firm at the time. There are 40 rooms containing 54,246 square feet (5,039.6 m2) of floor space, as well as 36 fireplaces.

The Society of the Congregational Church of Great Barrington (also known as First Congregational Church of Great Barrington) is an historic church building and parish house located at 241 and 251 Main Street in Great Barrington, Massachusetts. It is the fourth church of a congregation whose first meetings were held in 1743.

US Post Office–Great Barrington Main is a historic post office at 222 Main Street in Great Barrington, Massachusetts. It was designed by architect Lorimer Rich and completed in 1936. Its design is unusual, because the United States Postal Service was at that time trying to economize on building costs in part by using standardized plans; this building is a notable deviation from this. The building was listed on the National Register of Historic Places in 1986.

The Mahaiwe Block is a commercial and theater building in the heart of downtown Great Barrington, Massachusetts. In addition to smaller businesses, it houses the Mahaiwe Performing Arts Center, the town's only major performance space. It has been in virtually continuous operation since its construction in 1905. The building is located at 6-14 Castle St. and 314-322 Main St, and is listed on the National Register of Historic Places. The building's condition and fate in the 1990s was a major contributing factor in the establishment of local preservation ordinances. The building takes its name from an earlier structure on the site, which its owner called "Mahaiwe House".

Great Barrington is a town in Berkshire County, Massachusetts, United States. It is part of the Pittsfield, Massachusetts, Metropolitan Statistical Area. The population was 7,172 at the 2020 census. Both a summer resort and home to Ski Butternut, a ski resort, Great Barrington includes the villages of Van Deusenville and Housatonic.