1703 First schoolhouse in the Westport area built on the commons in Green's Farms.
1810 Levi T. Downes builds a general store on Main St., which was later used as a schoolhouse, and is now Tavern on Main.
1812 Teachers required to pass an examination in English grammar.
1837 Ebenezer Banks Adams founds Adams Academy, a coed prep school, on land of David Coley. For the thirty years of its operation, the school attracted students from all over the east coast, who boarded with Westport families.
1884 April 26 The first Staples High School is built on Riverside Ave., and opens with enrollment of 16 students.
1887 The first graduation of students from Staples High School.
1909 Control of Staples High School transferred from the estate of Horace Staples to the town of Westport.
1916 New wing added to Bridge Street School.
1917 Bedford Elementary School built on Myrtle Ave., with a major financial contribution from Edward T. Bedford.
1924 The original Bedford Junior High built, which became King's Highway Elementary.
1925 Green's Farms Elementary built.
1925 October Mary E. E. Bolton opens Mrs. Bolton's School for Girls, in a three-story frame house on Church Lane across from Christ and Holy Trinity Church. The School began with four students, but by the spring of 1926 the enrollment had increased to eighteen students aged seven and under.
1953 Coleytown Elementary School built.
1957 Burr Farms Elementary School built.
1957 October 22 The Kathleen Laycock Country Day School, serving students from Sixth through Twelfth Grades, is incorporated.
1958 The new Staples High School opens at 70 North Ave.
1959 November The Kathleen Laycock Country Day School moves to 35 Beachside Ave.
1961 -1962 Hillspoint Elementary School built.
1963 Westport's first Summer School program opens.
1964 Green's Farms Pre-school opens, at 71 Hillandale Rd.
1964 Bert Chernow, artist and art teacher at Green's Farms Elementary launches the Westport Schools Permanent Art Collection (WSPAC), with the ideal that all Westport children should be surrounded by art in the schools.
1964 A year after president John F. Kennedy's death, an eight-foot long bronze plaque commemorating Kennedy is placed on the outside wall of the Staples High School administration building: "Ask not what your country can do for you. Ask what you can do for your country."
1965 Coleytown Junior High built.
1969 October 15 1,200 students from Staples High School march from Staples to downtown Westport to protest the war.
1970 The Kathleen Laycock Country Day School changes its name to Greens Farms Academy, and begins its transition to a fully co-ed school by admitting 23 boys to a group of approximately 300 girls at the school.
1984 Green's Farms Elementary School is converted to the Westport Arts Center.
1996 Westport reclaims Green's Farms Elementary school back from the Westport Arts Center.
1997 The Teen Coffeehouse opens at historic Toquet Hall, providing a gathering place for Staples and Green's Farms Academy students.
2000 The Kids' Wall project is initiated. The 6-foot by 44-foot wall is composed of 64 individual panels, each panel created by one of the 64 art classes in the Westport Middle Schools, and is installed at the children's pool at Longshore.
2000 The Staples Players, under the direction fo Judy Luster, are chosen to represent the United States at the Edinburgh Theatre Festival.