Dellwood began its history many, many years ago. Its first location was on Church Street at the current location of the People's Pharmacy Toy Department.From there the school grew and moved to this location on North Street where it was organized as a primary School.

Mr. A. E. Nicholl was the chairman of the Board of Trustees for the original Dellwood School for twenty eight years, from 1940- 1968. He was a naval officer at HMS Dockyard and out of his interest for young people he felt that students should be trained in woodwork and metalwork. In consultation with the Department of Education, the Nicholl Institute was built. Students from various parts of the island came to Nicholl institute to receive their training. In the early 1960s, Nicholl became part of Dellwood proper. and subsequently became the woodwork and science departments of Northland's Secondary School. Today it is the Design & Technology Department of Dellwood Middle School, hence the name, The Albert E. Nicholl Building- Design & Technology.

Mr. Thomas F. Wyatt was the first principal of Dellwood Middle School and served from 1940 - 1961.  He believed that students should have a good, solid, all round education. It was during his tenure that the Infant Block was built.  Today, it houses the M1 students. In recognition to his service to the educational system and to retain the history of Dellwood, this building was named the Thomas F. Wyatt Wing.

Mr. Charles Williams  became the second principal of Dellwood. He served from 1961 - 1972 when Dellwood was an elementary school. During his tenure , Mr. Williams was instrumental in introducing secondary level education at Dellwood where he oversaw the construction of the west wing, the building housing the library and cafeteria. It was renovated in 1996-7.

In 1971, the Ministry of Education and the government of the day adopted a law to integrate the school system. This change saw Dellwood's secondary section move to the Berkeley Road site to become part of the reorganized Northland's Secondary School. Simultaneously, Dellwood Primary accepted students and teachers from Northland's Elementary School.

In 1963 Mr. Williams conducted research on the school crest. Its basic features are fixtures from the parish of Pembroke and from the coat of arms of the Ewing family. Mr. Ewing was a former speaker of the House of Assembly and originally owned Dellwood House (see below) and adjoining land on which the school exists. Mr. Williams added the book of knowledge, and motto: "Deeds Not Words". For his dedication to the education of young people at Dellwood, this wing is named the Wiiliam's Building.