Holmwood was established as the first Practical Training Centre on March 2, 1936. The initial enrolment was fifty male students who boarded at the school under the tutelage of Mr Edgar B. Rogers, the first Superintendent. At that time, the school owned Denham Farm in Chudleigh and there the boys practiced Practical Agriculture, Ancillary Disciplines of Woodwork, Book-Keeping and other related subjects were also taught.

In 1960 the school was converted to a Technical High School and Mr Winston B. Johnson appointed as Principal. The curriculum was therefore changed to traditional high school subjects with practical subjects such as Metal Work, Auto Mechanics, Woodwork, Technical Drawing, Cookery, Dressmaking, Typewriting, Accounts, Shorthand, Office Practice, Surveying and Electrical Installation. In 1961 the school became co-educational and offered boarding for the girls.

In 1974, under the guidance of Principal, Mr Ronald Hamilton, the school saw considerable physical expansion with the construction of a three –floor block of classrooms and six staff flats. In the 1980s Vocational Departments were added: the 1990s a Computer Laboratory was added; in 2002 the Sixth Form (CAPE) Programme was implemented; in 2007 Holmwood Extension School was launched; 2009 marked the beginning of the E-Learning Programme and 2010 marked the beginning of the CAP (HEART) Programme.

Since the school’s inception, Holmwood Technical has been a leader in innovative educational modules, having been the first Practical Training Centre, the first Rural Secondary High School and one of the first Technical High Schools in Jamaica. It is also one of the first schools to have a past student as Member of Parliament (MP) in its own constituency.

Some of the Principals who have guided Holmwood are:

Mr Edgar B. Roberts

Mr Fredrick R. Ricketts

Mr Winston B. Johnson

Mr Ronald Hamilton

Mr Paul Bailey (present)