In 1935, during the depths of the Depression, Wellesley was faced with a challenge. Within the previous forty years the town had built two high schools. The first, built in 1894 at 322 Washington Street, to accommodated 150 students was soon outgrown. The second, built in 1907 at 50 Kingsbury Street, to accommodate 350 students was also outgrown and proved inadequate for meeting educational needs. Wellesley would again have to build a new school and start from scratch on a new site. In early 1936, a survey of sites for a new school took into account the importance of a central location in town, access to existing play fields, and removal from hazards posed by traffic. (See Proposed Site Plan.) Five locations were proposed. Pro’s and con’s were listed for each one. The former Kingsbury Park on Rice Street (site E on the plan) was selected, and it is there the 1938 High School stands today. The capacity of this new building was set at 750 students.

“The physical characteristics of the site had an important bearing in the selection of a building plan because the long mound of relatively high ground on which the building is placed provided the proper northeast-southwest orientation for all of the principal rooms, and as it widens out at its northerly end. It provided sufficient area for the Auditorium wing without requiring a large expenditure for filling to properly landscape the building....” (1938 WHS Dedication Program)

The wisdom of the High School Building Committee in selecting this site was borne out in its capacity for future expansion and increased parking. Original plans included the provision for an addition of a classroom wing that would increase the capacity to 1100 students. This three-floor wing was built in 1956. It was designed to accommodate the addition of a fourth floor when needed; this floor never materialized. Six further additions have since been made to the original 1938 building.