High School at the Head of Westport. The high school at the Head of Westport was locally referred to as the "Head School." In 1866 a committee of three was named to investigate the question of a high school. At Town Meeting 1868 the committee recommended building a high school at the Head of the East River for 18 weeks and that a tax levy of $1000.00 be imposed. The Town agreed to build the school provided that it be operated for the full school year "unless a good place was found at the Point."

The first curriculum for high school studies was drawn up in 1888 and was a two-year program. A four-year study course was established in 1922-23, 30 years later. The first class was graduated from Westport High School in June 1923 and had seven students.

Ca. 1890, the high school was moved from the Head of Westport to Westport Point for a time before moving to the old Town Hall in Central Village. The Head School was used for the Westport School Administration offices and as an elementary school. It now (2004) houses Westport's Council on Aging. (Roy et al. "Early Schooldays in Westport." 1989:pp. 49-50, 72-73.)