The first school in Stockbridge was opened in 1737 under the direction of John Sergeant, a missionary to the local Mohican Indians.
 It served as a school for the Christian education of Indian children.
 During the pre-American Revolutionary War years, several small schools were established to serve the children of new settlers scattered further outside the village.
The founding of the semi-private Academy after the Revolutionary War marked the beginning of a more structured commitment to secondary education in the town.
 Three of the four students in the first graduating class of Williams College in 1795 were alumni of the Academy.

In the early and mid-1800s Stockbridge schools earned the distinction of educating three Associate Justices of the Supreme Court of the United States who served on the high court at the same time.
All educated in Stockbridge, Stephen Johnson Field, Henry Billings Brown and David Josiah Brewer served together as Associate Justices from 1891 to 1897.

Students from Stockbridge, its small villages of Interlaken, Glendale and Larrywaug, and from the nearby town of West Stockbridge attended the town's Williams High School, established in 1872.
 In April 1968 the school closed after nearly a decade of contentious school regionalization debates and failed ballot measures.
After the state refused in 1964 to help fund a new high school building, Stockbridge voters approved a regionalization plan to join Great Barrington and West Stockbridge in a consolidated school district.
 In 1968 Stockbridge students joined those from Great Barrington's Searles High School in transferring to a new regional high school located in Great Barrington.

The building of the former Stockbridge Plain School, completed in 1914, was shared by the elementary school and Williams High School, until the opening of Monument Mountain Regional High School in 1968.
Stockbridge Plain School for several years then became one of the elementary schools in the new Berkshire Hills Regional School District.
A renovation of the building was completed in 2008, and it now serves as the new town offices.

Today, Stockbridge, along with West Stockbridge and Great Barrington, remain members of the Berkshire Hills Regional School District.
All students in the district attend school in Great Barrington, with elementary students attending Muddy Brook Regional Elementary School, middle school students attending Monument Valley Regional Middle School, and high school students attending Monument Mountain Regional High School.
In addition to public schools, there are private and religious schools located in the neighboring towns.

The nearest community college is the South County branch of Berkshire Community College in Great Barrington.
The nearest state college is Massachusetts College of Liberal Arts in North Adams, and the nearest state university is the University of Massachusetts Amherst.
The nearest private college is Bard College at Simon's Rock, also in Great Barrington.
 Less than an hour's drive away, in Albany, New York, is a state university, University at Albany, SUNY, and also several private colleges.
The first school in Stockbridge was opened in 1737 under the direction of John Sergeant, a missionary to the local Mohican Indians.  It served as a school for the Christian education of Indian children.  During the pre-American Revolutionary War years, several small schools were established to serve the children of new settlers scattered further outside the village. The founding of the semi-private Academy after the Revolutionary War marked the beginning of a more structured commitment to secondary education in the town.  Three of the four students in the first graduating class of Williams College in 1795 were alumni of the Academy.
In the early and mid-1800s Stockbridge schools earned the distinction of educating three Associate Justices of the Supreme Court of the United States who served on the high court at the same time. All educated in Stockbridge, Stephen Johnson Field, Henry Billings Brown and David Josiah Brewer served together as Associate Justices from 1891 to 1897.
Students from Stockbridge, its small villages of Interlaken, Glendale and Larrywaug, and from the nearby town of West Stockbridge attended the town's Williams High School, established in 1872.  In April 1968 the school closed after nearly a decade of contentious school regionalization debates and failed ballot measures. After the state refused in 1964 to help fund a new high school building, Stockbridge voters approved a regionalization plan to join Great Barrington and West Stockbridge in a consolidated school district.  In 1968 Stockbridge students joined those from Great Barrington's Searles High School in transferring to a new regional high school located in Great Barrington.
The building of the former Stockbridge Plain School, completed in 1914, was shared by the elementary school and Williams High School, until the opening of Monument Mountain Regional High School in 1968. Stockbridge Plain School for several years then became one of the elementary schools in the new Berkshire Hills Regional School District. A renovation of the building was completed in 2008, and it now serves as the new town offices.
Today, Stockbridge, along with West Stockbridge and Great Barrington, remain members of the Berkshire Hills Regional School District. All students in the district attend school in Great Barrington, with elementary students attending Muddy Brook Regional Elementary School, middle school students attending Monument Valley Regional Middle School, and high school students attending Monument Mountain Regional High School. In addition to public schools, there are private and religious schools located in the neighboring towns.
The nearest community college is the South County branch of Berkshire Community College in Great Barrington. The nearest state college is Massachusetts College of Liberal Arts in North Adams, and the nearest state university is the University of Massachusetts Amherst. The nearest private college is Bard College at Simon's Rock, also in Great Barrington.  Less than an hour's drive away, in Albany, New York, is a state university, University at Albany, SUNY, and also several private colleges.
Stockbridge, Massachusetts