In 1854, at the annual Town Meeting at Wayland, residents voted to build the community’s first High School, this structure, which was completed in 1855. The roughly square building is Italianate in style with the round arched windows and bracketed cornice, but with some holdover features common in Greek Revival architecture, including the tall pilasters dividing the bays, and projecting portico supported by square paneled columns. A few years after opening, the new High School was so underused, the local grammar school held some classes here. By the 1880s, high school students were sent to school outside of town. As the town population began to increase and the size of the student body necessitated a new high school. The town considered repair of this building, which had suffered from neglect, or construction of a new building. In the end, money was appropriated to build a new High and Grammar School in 1896. The town had the first school moved slightly on the town lot to allow space for the new, second school, and sold the 1850s schoolhouse to the local chapter of the Independent Order of Odd Fellows, known as Pequod Lodge. The second high school was demolished in 1978, over a decade after the present High School was built by The Architect’s Collaborative (TAC). In 1978, the Old Wayland High School was sold to the neighboring Trinitarian Church and has been used for administrative purposes and church meetings.