The Mahican Indians called the area Mahaiwe, meaning “the place downstream”. It lay on the New England Path, which connected Fort Orange near Albany, New York, with Springfield and Massachusetts Bay.

The first recorded account of Europeans in the area happened in August 1676, during King Philip’s War. 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. According to reports at the time, Talcott’s troops killed twenty-five Indians and imprisoned another twenty. Today, a plaque for John Talcott marks the spot where the massacre is believed to have happened.

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. The Konkapot River in southwestern Massachusetts is named after him.

The village was first settled by colonists in 1726 and from 1742–1761 was the north parish of Sheffield. In 1761, it was officially incorporated as Great Barrington, named after the village of Great Barrington in Gloucestershire, England.

In the summer of 1774, 1,500 men shut down the Berkshire County Court in response to British oppression. In the winter of 1776, Henry Knox passed through Great Barrington while transporting the cannon from Fort Ticonderoga to the Siege of Boston. Due to his time in the area, he established an agricultural interest in the area of Great Barrington.

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.

Among the earliest estates was one built by New York City banker, industrialist and art patron David Leavitt, who built an elaborate 300-acre (1.2 km²) estate, and was soon followed by those of his sons nearby. Leavitt was instrumental in the development of the local Housatonic Railroad, serving as its president.

Later estates included Searles Castle, commissioned in 1888 by the widow of Mark Hopkins together with her second husband, Edward Francis Searles, and “Brookside”, built for William Hall Walker. 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.

Great Barrington is the birthplace of W. E. B. Du Bois, an African-American academic and civil rights activist, most known for being one of the co-founders of the National Association for the Advancement of Colored People (NAACP) in 1909. Du Bois was born on February 23, 1868, at a house later replaced by where present-day Route 23 would run. As a child, Du Bois attended the Congregational Church. Many of these church members donated the funds needed for Du Bois to attend college. Du Bois lived in the town until he was seventeen. The W.E.B. Du Bois Boyhood Homesite has interpretive trails and a walking tour.

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. Stanley felt AC was an improvement over the direct current system being used by Thomas Edison, and Stanley was trying to get Westinghouse to adopt it. Stanley had developed a series transformer he thought would make AC practical. 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. Stringing the power lines from tree to tree down the street, in March 1886 Stanley powered the system up and was able to expand it to the point where it could light 23 businesses along Main Street with very little power loss over 4,000 ft (1,200 m). The system’s 500 AC volt current was stepped down to 100 volts using the new Stanley transformer to power incandescent lamps at each location. This was the world’s first practical demonstration of a transformer/alternating current system and the basis of the AC systems Westinghouse would begin installing later that year.

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.

On October 18, 1990, Richard Stanley purchased the old Miller Hotel, also known as the Barrington House. Stanley started to upgrade the building, evicting tenants who had been involved in drugs. He removed the 1960s aluminum facade and returned the historic building through renovation to its 1929 appearance.

The town was the site of an F4 tornado around 7:00 PM on Memorial Day, May 29, 1995. The tornado killed three people and caused damage in the area.

On November 15, 1995, Richard Stanley and Joseph Wasserman opened The Triplex Cinema in the heart of Great Barrington. This contributed to further developments in the town, changing the economy and enhancing its desirability by providing a place for community events. With increased appeal as a destination, the town attracted new restaurants and retail shops, which opened on both Main Street and Railroad Street. Both streets previously had many vacant shops. The Berkshire Eagle reported Great Barrington had 50 places to eat in a town of 7,700 people.

On July 24, 2009, Great Barrington was named an Appalachian Trail Community by application and acceptance by the Appalachian Trail Conservancy.

On June 1, 2010, a new fire station was opened for the Great Barrington Fire Department, located on Route 7. The new fire station replaced the old one, on Castle Street. It had deteriorated and was too small for the growing needs of the fire department. The new $9.1 million facility was planned as a center for community events such as elections. It serves as the hub for emergency operations in southern Berkshire County.

The town celebrated its 250th anniversary with a large parade on July 10, 2011. Other events celebrating the 250th anniversary were held throughout the year as well.

The “Main Street Reconstruction Project” was launched in 2011, involving major improvements along Main Street between Saint James Place and Cottage Street. 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. The project had finished its design phase as of 2012, and construction was to be completed in 2016.

As of the census of 2000, there were 7,527 people, 3,008 households, and 1,825 families residing in the town. By population, the town ranks fifth out of the 32 cities and towns in Berkshire County, and 202nd out of 351 cities and towns in Massachusetts. The population density was 166.6 people per square mile (64.3/km²), ranking it eighth in the county and 268th in the Commonwealth. There were 3,352 housing units at an average density of 74.2 per square mile (28.6/km²). The racial makeup of the town was 94.74% White, 2.09% Black or African American, 0.16% Native American, 1.25% Asian, 0.03% Pacific Islander, 0.70% from other races, and 1.04% from two or more races. Hispanic or Latino people of any race were 2.07% of the population. 17% were of Irish descent, 12% Italian, 11% German, 10% English and 9% Polish.

There were 3,008 households, of which 27.3% had children under the age of 18 living with them, 45.8% were married couples living together, 11.5% had a female householder with no husband present, and 39.3% were non-families. 32.6% of all households were made up of individuals, and 13.3% had someone living alone who was 65 years of age or older. The average household size was 2.28 and the average family size was 2.89.

In the town, the population was spread out, with 22.6% under the age of 18, 9.0% from 18 to 24, 23.5% from 25 to 44, 26.2% from 45 to 64, and 18.8% who were 65 years of age or older. The median age was 42 years. For every 100 females, there were 87.2 males. For every 100 females age 18 and over, there were 83.8 males.

The town’s median household income was $95,490, and the median family income was $103,135. Males had a median income of $68,163 versus $49,474 for females. The town’s per capita income was $42,655. About 2.4% of families and 5.2% of the population were below the poverty line, including 3.6% of those under age 18 and 2.5% of those age 65 or over.

Great Barrington employs the open town meeting form of government, and is led by a board of selectmen and a town manager. Great Barrington has its own public services, including police, fire and public works departments. The town has two libraries, with the main branch, Mason Library, at 231 Main Street in Great Barrington, and a branch library, Ramsdell Library, at 1087 Main Street in the village of Housatonic, both of which are part of the regional library network. The town is home to Southern Berkshire District Court, as well as Fairview Hospital, the largest hospital in the southern end of the county (based on the number of beds).

On the state level, Great Barrington is represented in the Massachusetts House of Representatives by the Fourth Berkshire district, which covers southern Berkshire County, as well as the westernmost towns in Hampden County. In the Massachusetts Senate, the town is represented by the Berkshire, Hampshire and Franklin district, which includes all of Berkshire County and western Hampshire and Franklin counties. The town is patrolled by the Great Barrington Police Department which is a 24/7/365 service.

On the national level, Great Barrington is represented in the United States House of Representatives as part of Massachusetts’s 1st congressional district. Democrat Richard Neal of Springfield has represented the district since 2012.

Great Barrington has a paid by call Fire Department, The Great Barrington Fire Department (GBFD), consists of about 40 members and five pumpers, one tower ladder, two rescue vehicles, and one brush truck. Most members are trained to the First Responder level; some are trained to the EMT-Basic level. The Fire Department responds to about 600 calls per year, which vary but are mainly fire alarm activations and medical emergencies.

Great Barrington’s Emergency Medical Services are covered by Southern Berkshire Volunteer Ambulance Squad Inc. (SBVAS), operated from the grounds of Fairview Hospital. The service provides 24/7/365 paramedic level service to the towns of Great Barrington, Housatonic, Alford, Egremont, Sheffield, Ashley Falls, Monterey, and Mount Washington. SBVAS is the primary paramedic intercept service for ambulances going into Fairview, including New Marlborough, Sandisfield, and Otis. The squad consists of a mix of full-time EMTs, paramedics, and volunteer EMTs. The squad responds to 3,000 to 5,000 calls a year.

Great Barrington offers the use of its own local currency, called BerkShare notes. There are about 844,000 BerkShare notes in circulation worth about $801,800 at the exchange rate of one BerkShare to 95 U.S. cents, according to program organizers. The paper money is available in denominations of one, five, ten, twenty, and fifty. Proponents say the currency gets residents to shop at local stores. Local areas may have their own currencies as long as they do not resemble the United States dollar and are in paper only.

Great Barrington is served by the Berkshire Regional Transit Authority, which offers bus transportation throughout Berkshire County. Peter Pan Bus Lines and Greyhound Lines have stops in Great Barrington for long-range bus transportation. 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. The nearest international airports are Bradley International Airport in Windsor Locks, CT, and Albany International Airport in Colonie, NY.