Its history evolved from the town's earliest schools founded before and shortly after the American Revolutionary War.
[1] The first school in Stockbridge was erected in 1737 under the supervision of John Sergeant, a missionary to the local Mohican Indians.
Through the pre-Revolutionary War years several small schools were opened to serve the children of newly arriving settlers scattered between the distant boundaries of adjoining towns.
[2] 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.
All educated in Stockbridge, Stephen Johnson Field,[3] Henry Billings Brown[4] and David Josiah Brewer[5] served together as Associate Justices from 1891 to 1897.
In addition to traditional business and college preparatory classes, there was a strong Future Farmers of America (FFA) chapter that attracted students from outside the district.
Boys varsity sports included soccer, basketball, skiing, baseball, cross country and golf.
[13] In September 1963 Stockbridge voters overwhelming decided, by a 298 to 55 majority, to build a new facility for Williams High School.
A site was chosen in fields below the Naumkeag estate north of the town center on land controlled by The Trustees of Reservations.
Planning began for their primary and secondary schools to be located on adjoining campuses in Great Barrington.
[15] Helping to manage the closure and transition was Henry L. O'Connor, the last principal to lead Williams High School.
Pressure from the state, economies of scale for rural districts and fluctuating student populations had forced the closure of its high school, an outcome Stockbridge resisted for over a decade.
Additionally, the building provides space for the police department, regional school district administration and a community gymnasium.
Oh fling out old Williams banner, flash its green upon the breeze, let its gold gleam in the sunshine, high above the smiling trees.
So let the green then wave in triumph, let the gold flash in the sun, as a bold and brave defiance, that her loyal sons are one.
Though the years may fade her colors, fleck the green and dull the gold, yet our hearts will e’er be loyal to old Williams as of old.