Bard Academy at Simon's Rock

Bard College at Simon's Rock (more commonly known as Simon's Rock) is a private liberal arts college in Great Barrington, Massachusetts. It is part of Bard College in Annandale-on-Hudson, New York. The school is an "early college", designed for students to enroll immediately after completing the tenth or eleventh grade, rather than after graduating from high school. Simon's Rock is the only accredited four-year early college to date and still the only college or university to take this approach with all of its students. It is one of a number of early college entrance programs that provide opportunities for students to enter college one or more years ahead of their traditional high school graduation date. A majority of students transfer to larger institutions after receiving an Associate of Arts degree after two years, although many stay for four to receive a Bachelor of Arts.

On December 14, 1992, a mass shooting occurred at Bard College at Simon's Rock in Great Barrington, Massachusetts, United States. A student and a professor were killed, and four others were injured, before the gunman, Wayne Lo, surrendered to police. He is currently serving two life sentences without the possibility of parole plus 20 years.

WBCR-LP is a low power FM radio station with office and studio located in Great Barrington, Massachusetts, broadcasting on the 97.7 FM frequency. The organization's legal name is "Berkshire Community Radio Alliance," and is also known as "Berkshire Community Radio" or "BCR." WBCR-LP is a 501(c)(3) non-profit, volunteer-run, non-commercial, community radio station with over 70 locally produced shows currently on the air. With a broadcast radius between 8 and 15 miles, depending on terrain, it serves the southern portion of Berkshire County, Massachusetts. WBCR-LP also streams live on the internet.

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

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.

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

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.

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.

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.

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 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.”

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.