Holmwood, the blessed school on the hill, is located in Sedburgh, North-east Manchester, on the Island of Jamaica. It was established as Jamaica's first Practical Training Centre in May 1936, headed by Mr. Edgar B. Rogers, the first Superintendent. It was then a vocational/trade school with an enrolment of fifty male students. Students were exposed to several disciplines such as - Woodwork, Bookkeeping, Shoemaking, Tailoring, Auto Mechanics, Building Construction and Carpentry, with the main focus being Agriculture.

During this time, the students made all the furniture to supply the various departments within the school, as well as other government schools across the Island. Because of the agricultural emphasis, the school owned a farm known as Denham Farm in Chudleigh. The agricultural bias allowed the institution, along with two others (Knockalva Training Centre and Dinthill Practical Centre) to serve as a feeder schools to the then Jamaica School of Agriculture.

In 1938 , the school was converted from a vocational school to a Practical Training Centre. Students came from as far as the Turks and Caicos Islands. In 1939, the school became a boarding institution. This gave way to the building of Richards Hall , which was used as the school's dormitory.

By September 1961, the school was converted to a co-educational institution and the transition from Practical Training Centre and later Rural Technical High, to a full Technical High School occurred. With this transition, there was a considerable increase in the population as improvement in facilities was provided by the government through US AID. The students were placed into four streams serviced by an academic staff of twenty-five.

As a technical school, Mr. Winston B. Johnson was appointed the first principal of the school in 1961 . By this time, agriculture was discontinued and Denham Farm was sold. The curriculum now had a wider range of disciplines, and traditional High School subjects were offered. These included: Agricultural Science, Chemistry, Physics, Biology, Art, Geography, History, English Language and Spanish. Practical subjects such as Metal Work, Auto Mechanics, Technical Drawing, Cookery, Dressmaking, Accounts, Typewriting, Shorthand, Office Practice, Surveying and Electrical Installation were also offered. In 1970, Mr. Johnson was succeeded by Mr. Ronald Hamilton, who in 1996, was in turn succeeded by Mr. Paul Bailey, the current principal.

1986 was a milestone year in the life of the school, as it celebrated its fiftieth anniversary. The celebrations kicked off with a church service in Christiana, with the Governor General, the Hon. Sir Florizel Glaspole as the guest speaker.

Over the years Holmwood has excelled in the field of sports. There have been major successes in Volleyball, Cricket, Netball and Athletics. In addition, there have also been successes in Music and Speech with the students gaining gold and silver medals in the JCDC (Jamaica Cultural Development Commission) competitions. Quite recently, the school has been doing well at the Spanish Festivals. Many of the students who have participated in the sporting arena have gained positions and scholarships to various colleges and universities locally and abroad. They have also represented the school and Jamaica at local and international meets. The athletic season for the years 2003-2006 has been great ones for the school as the female athletes have dominated the National Girls' Athletics Championships .

Holmwood students have also excelled in academics and the school has received letters of commendation from the Ministry of Education on their successes. Students have gained scholarships and commendations from various sectors locally and internationally, for outstanding performances. In 2002, the sixth form program was introduced, offering CAPE (Caribbean Advanced Proficiency Examinations). The pioneer batch graduated in 2004, having acquainted themselves well in the examinations .

The school's successes would not have been possible without the support of the academic, administrative and auxiliary staffs along with the PTA, Board of Governors and the various chapters of the Holmwood Past Students Association.