It lay on the New England Path, which connected Fort Orange near Albany, New York, with Springfield and Massachusetts Bay.

[2] Major John Talcott and his troops chased a group of 200 Mahican Natives west from Westfield, eventually overtaking them at the Housatonic River in what is now Great Barrington.

[3] On April 25, 1724, Captain John Ashley of Westfield, Massachusetts, bought on behalf of himself and a committee of the Massachusetts General Court the land that became the towns of Great Barrington, Sheffield, Egremont, Alford, Mount Washington, and Boston Corner for £460, three barrels of "sider," and thirty quarts of rum from 21 Native American sachems headed by Conkepot Poneyote.

[5] In the summer of 1774, local colonists temporarily forced the closure of the Berkshire County Court in response to unpopular British policies.

With the arrival of the railroad in the late 19th century, Great Barrington developed as a Gilded Age resort community for those seeking relief from the heat and pollution of cities.

Wealthy families built grand homes called Berkshire Cottages here, as others would in Lenox and Stockbridge.

In 1895, Colonel William L. Brown, part owner of the New York Daily News, presented Great Barrington with a statue of a newsboy, now a landmark on the western edge of town.

[8] In November 1885 electrical engineer William Stanley, Jr., a sometime Great Barrington resident working for George Westinghouse, began installing a demonstration transformer based alternating current lighting system.

He built his components at the "Old Rubber Factory" south of Cottage Street and installed a Westinghouse steam engine powering a 500 volt Siemens generator.

[10] Arlo Guthrie's song "Alice's Restaurant," which runs for 18+1⁄2 minutes, is based on true-life events of the mid-20th century in Great Barrington and the adjoining towns of Stockbridge and Lee.

The Old Trinity Church, which was the home of Ray and Alice Brock at the time of these incidents, is now owned by Guthrie, and is at 4 Van Deusenville Road in Great Barrington.

The plan elements include new pavement, new sidewalks, sewer and utility improvements, and the removal of the large pear trees that span Main Street, to be replaced with a much wider array of trees of varying sizes and growth habits.

[17] In 2023 the town made national news after plainclothes police conducted a search of the WEB DuBois Regional Middle School based on an anonymous tip that someone in the school possessed a copy of the book Gender Queer: A Memoir.

The Appalachian Trail crosses through East Mountain State Forest in the southeast corner of town.

The Berkshire Humane Society operates animal welfare services and pet adoption facilities in the town.

Great Barrington's Emergency Medical Services are covered by Southern Berkshire Volunteer Ambulance Squad Inc. (SBVAS),[41] operated from the grounds of Fairview Hospital.

SBVAS is the primary paramedic intercept service for ambulances going into Fairview, including New Marlborough, Sandisfield, and Otis.

Local areas may have their own currencies as long as they do not resemble the United States dollar and are in paper only.

Originally at MIT, it relocated to the southern shore of Great Barrington's Long Pond in 1946.

In October 2020 the Institute held a meeting of epidemiologists, economists and journalists to discuss government responses to the COVID-19 pandemic.

The result was the Great Barrington Declaration, signed at the Institute's headquarters on October 4, 2020, and released to the public the following day, which advocated an alternative, risk-based approach to the pandemic involving "focused protection" of those most at risk and seeking to avoid or minimize the societal harm of lockdowns.

Muddy Brook Regional Elementary School offers pre-kindergarten through fourth grade classes and is off Route 7 in the northern part of town.

The town lies along the Housatonic Railroad line, which roughly follows Route 7 and the river through southern New England.

Walter J. Koladza Airport is in Great Barrington, and features a full service FBO for general aviation aircraft.