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Fairview Hospital is a private, non-profit 25-bed health care facility in Great Barrington, Massachusetts, owned by Berkshire Health Systems.

The Taconic and West Avenues Historic District is a largely residential historic district south of the downtown area of Great Barrington, Massachusetts. The roughly 117-acre (47 ha) district includes 172 contributing elements, most of which are houses or related buildings. Two thirds of the buildings were built between 1890 and 1910, and most of the rest were constructed in a historically sympathetic way.The southwestern corner of the district is the intersection of Maple and West Avenues. Its western boundary is a high wooded ridge that roughly parallels Castle Street, and follows Main Street and Maple Avenue on its eastern and southern boundaries. The housing in the district was built by Great Barrington's wealthier residents, and feature large houses built in a variety of popular styles of the period. The district features Georgian, Early Republic, and Mid 19th-Century Revival architecture. It was added to the National Register of Historic Places in 1998.Great Barrington was settled in the 18th century, and was the first county seat of Berkshire County. It developed around a major crossing of the Housatonic River, which also provided power for industry. Early development in this district occurred primarily along Main Street, where houses such as the Dwight–Henderson House were built, and Taconic Street, a major road leading northwest toward Alford. Development in the district was modest through much of the 19th century, only becoming more organized in the 1880s, when a number of cross streets were laid out for residential development.

The John Dewey Academy is a private, coeducational college preparatory therapeutic boarding school in Great Barrington, Massachusetts, formerly housed in Searles Castle. It was founded in 1985 by Dr. Thomas E. Bratter, who died in 2012. In May 2020, the school was purchased by its current head of school, David Baum. As of July 2022, the school was on hiatus for a "complete reboot" at a new location. It is coeducational and enrolls about 25 high school students, ages 15 to 21, typically in grades 10 to postgraduate. The student-teacher ratio is 3:1 and classes typically average about six students. On their website, the academy states that all graduates attend college.The John Dewey Academy has been cited to use Caring Confrontation Psychotherapy (CCP) as its primary form of treatment, a form of therapy created by Tom Bratter. CCP's critics refer to it as "attack therapy" and point to its consistent use in institutions that have been shut down for abuse, such as Synanon, CEDU, and the Elan School. A 2011 blog post from the John Dewey Academy addressed and criticized the closure of the Elan School, attributing its allegations and subsequent closure to "the corrosive influence of the rumor mill as well as misconceptions about programs fostered by gossip and false information" before promoting the academy itself as an option for those who were looking to attend a school like Elan. It is unclear whether the John Dewey Academy follows in this abusive pattern, as there have been no formal studies of the John Dewey Academy other than those done by its founder, Tom Bratter. These studies primarily consist of Bratter providing predominantly anecdotal evidence of the academy's successes and asserting that "the John Dewey Academy’s treatment results are the best of any residential program that provides intensive therapeutic and education for alienated adolescents who require residential placement."The school was listed in the Boston Globe's Spotlight study of abuse in private schools, which specifically identified lawsuits against founder Thomas Bratter and faculty Gwendolyn Hampton.In March, 2021, the Berkshire Eagle came out with an exposé about the abuse at the John Dewey Academy titled "Former students of Great Barrington prep school describe it as 'torture chamber'" In response, the school closed in 2022, with Baum stating "“Reboot, revise, re-staff — everything’s on the table.”

The Dwight–Henderson House is a historic house at 390 Main Street in Great Barrington, Massachusetts. It is the second oldest house in Great Barrington, built in 1759 for Joseph Dwight, a brigadier in the colonial militia, by local builder Daniel Allen. The saltbox home was originally built into a slope, and had three stories on the front and one in the rear. The house has been moved twice, but remains within 200 feet (61 m) of its original site. The second move, the foundation that formed the wall for the original first floor, so it now presents only two stories in front.The house is notable for several historical associations. In addition to General Dwight, who was also town moderator and selectman, and a county judge, the houses notable guests include British General John Burgoyne, who surrendered his army after the Battles of Saratoga in 1777, and spent several days here while en route to the Boston area as a prisoner. It is also the house where poet and newspaper editor William Cullen Bryant was married; he was a guest of the owner, Allen Henderson.Since then, the house has seen a variety of uses. It served for a time as housing for the nearby Berkshire Motor Inn, and now houses professional offices. The house was listed on the National Register of Historic Places in 1976, and included as a contributing property to the Taconic and West Avenues Historic District in 1998.

Great Barrington station is a former railroad station in Great Barrington, Massachusetts along the Housatonic Railroad Berkshire Line.

The Mahaiwe Performing Arts Center () is a major performance space in the town of Great Barrington, Massachusetts. The theater's name comes from the indigenous Mahican term for "the place downstream" in relation to the Housatonic River. The theater itself has hosted events for the Berkshire County community since it was built in 1905 and as the performing arts center since 2005, with offerings ranging from movies to live music, dance, drama, and comedy.

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".

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.

Great Barrington is a census-designated place (CDP) located in the town of Great Barrington in Berkshire County, Massachusetts, United States. The population was 2,231 at the 2010 census, out of 7,104 in the entire town of Great Barrington.

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.

The Clinton African Methodist Episcopal Zion Church is a historic church at 9 Elm Court in Great Barrington, Massachusetts. It was the first African American church in Berkshire County, and it was a place where noted Great Barrington native W.E.B. Du Bois is known to have attended services. The Shingle style church was completed in 1887, and continues to serve as a center of African American worship in southern Berkshire County.

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.