1864:  Wolfville's first free school was built on the corner of Highland and Acadia Streets on what is now the school playground.  It was not highly thought of, being described as "rough and awfully dirty".  It shared the building with the town jail and also housed the firebell.

1893 saw completion of the MacKay School on Acadia Street.  It was named for the provincial superintendent of education, and considered one of the most modern in the county.  By 1897 it was educating students up to grade 10 and 11 level.

1907:  W.H. Chase, the apple king, gave books to the school library.

1909:  An anti-cigarette league was formed among the boys, who wore special maple leaf badges.

1920:  A night school began in the school building, for those who wished to improve their education.

1921:  The original 1864 school was torn down, and a new building, the Munro School, was erected.  The architect was a former teacher, Leslie R. Fairn, and it was constructed by Wolfville's foremost contractor, Charles H. Wright.  Primary classes continued in the MacKay School while grades 5 to 11 occupied the Munro.  B.C. Silver was principal from 1922 to 1940, and O. Rex Porter held the position for the next 30 years. The drama program at the school was popular and successful, as were track and field meets.

1926:  the original Wolfville School of 1864 was demolished to enlarge the primary playground.

1927:  for the first time the Compulsory Attendance Act was enforced in Wolfville.

1928:  School colours were adopted - powder blue (later royal blue), black and gold.

1935:  Local students won eleven of the eighteen prizes offered for English composition by the Ceylon Tea Company of Montreal, including first prize which went to Ernest Forbes Young.

1940s:  A cadet program was organized to train boys for the armed services and achieve proficiency in drill and marksmanship.  The cadet band was a popular feature of the program.

The post war baby boom meant that school boards everywhere had to prepare for the expected rise in the student population.  In the 1950s the Tabernacle building (now the Royal Canadian Legion on Main Street)  was purchased for Industrial Arts and Continuing Education. 

1955: the house next to the Munro Building on Acadia Street was purchased and renamed the B.C. Silver Building.  Continuing the eastward expansion along Acadia Street, the Longley property was bought and the house relocated.  This gave the needed space for the construction of a new high school.

1956: Wolfville High School built.

1964:   Gladys I. West  retired after teaching for 52 years in Wolfville, and was honoured by staff and students alike.  New offices, a library and teachers' room were added to the high school and another half million dollar extension voted.

1965: The B.C. Silver building was demolished making room for a gymnasium addition to the high school.  By the 1970s parents were urging the replacement of the venerable MacKay building as well as the Munro building to allow the building of a modern elementary school.

1972:  By late fall the older school buildings were gone and classes had begun in a new elementary school, designed by Leslie R. Fairn, and constructed by V.C. Woodworth.  It featured the new "open classroom concept".

1973:   The formal opening of the new school took place in January 1973.  After more than a century of building and rebuilding, the Wolfville School had achieved the form that it still has today.

1977:   Despite opposition that included a brief sit-in by the students, Wolfville became part of the amalgamated county school board and the high school classes ceased.  Students from grades 10 to 12 now attend Horton District High School in Greenwich.