The school seemed to change names, and locations; but, for the most part, it was run by the same person, Leopold Gilbert Blackman.
Born on July 4, 1874 in Cheltenham, England, Blackman was the son of Thomas and Harriet (Sutherland) Blackman. He was an associate of Saint Nicholas College, Lancing, England, and was principal of the preparatory school of Ardingly College before coming to Hawaiʻi. (Builders of Hawaiʻi)
At the request of the Bishop Willis, Blackman arrived in the Islands in 1900 to take charge of ʻIolani School. He served as head of school at ʻIolani for one year; then, he was an assistant at Bishop Museum 1901-09 (also serving as editor of the Hawaiian Forester and Agriculturist.)
Then, he went back to school.
It started with Aliʻiolani College, in Pālolo. “Aliʻiolani College was an offshoot from the ʻIolani (school.)” (Thrum)
“Aliʻiolani College, started a few years ago in a cottage, has now quite arrived as a respectable acquisition to Honolulu’s fine array of public and private schools. It appears to supply a distinct want for its neighborhood, besides aiding to solve the problem of school congestion for the city.” (Hawaiian Star, June 21, 1910)
“(T)hrough the generosity of Mrs Mary E Foster, foundress of the college, permanent buildings had been erected sufficient for all present needs and in many other ways progress had been made toward making Aliʻiolani an efficient unit of the splendid Honolulu family of educational institutions.” (Hawaiian Star, June 21, 1910)
(Daughter of James Robinson, Mary Robinson married Thomas Foster, an initial organizer of the Inter-Island Steam Navigation Company. That company founded a subsidiary, Inter-Island Airways, that later changed its name to Hawaiian Airlines. Their home later became Foster Botanical Garden.)
“Among our many well equipped establishments we believe that Aliʻiolani has a definite destiny as a boys’ boarding school, offering at moderate fees a substantial education soundly based upon the elementary branches of Instruction, an education in which habits of discipline cheerful obedience to constituted authority, courtesy and loyalty are given a recognized place as adjuncts to true manhood.” (Blackman, Hawaiian Star, June 21, 1910)
However, that school on that site had a short stay.
The building and grounds of the Aliʻiolani College was offered to the board of education “for the establishment of vocational schools … rent free for four months or until the legislature provides ways and means for maintaining the schools.”
“The offer of Aliʻiolani has been made by the owner, Mrs. Nellie E. Foster, who has also offered to contribute generously towards a fund to meet running expenses.” (Hawaiian Gazette, May 24, 1912)
A Department of Education Biennial Report for 1912 notes Blackman as principal of the Honolulu School For Boys, it was divided into three departments: Preparatory, Grammar School and High School. “The Honolulu School for Boys, at Kaimukī, (was) an independent boarding and training school, originally the Aliʻiolani College.” (Thrum)
“The campus comprises eighteen acres and is situated in the salubrious Ocean View district of Honolulu. Extensive views of mountain range and ocean are obtained, while continual trade breezes temper the air and render residence at the school pleasant and healthful.”
“The main building consists of a two-story edifice with two one-story wings. The ground floor is devoted chiefly to class rooms and dormitories. Of the wings, one furnishes a dining hall; the other, the matron’s residence, is chiefly devoted to the use of the smaller boys. All dormitories are upstairs, are well ventilated and lighted and open upon spacious lanais.”
“The increasing enrollments of the school necessitated an additional building to be erected in the summer of 1912, known as the Grammar School. This new structure is of two stories—the upper one being devoted to dormitory accommodations and the lower one to class rooms.” (DOE, 1912)
The school later moved into lower Kaimukī, and, again, changed its name – and the old campus was converted to a hotel.
“For some time the place (former Aliʻiolani campus in Pālolo) remained vacant but recently was run as a boarding house until take over by King, who has renovated the building and started a modern hotel. It has been renovated, remodeled and improved and will be known as Aliʻiolani Hotel.” (Honolulu Star-bulletin, September 19, 1916)
Honolulu School for Boys changed its name to Honolulu Military Academy. (Thrum, 1917) “It was controlled by a board of 10 trustees of which the president (Blackman) was a member and presiding officer ex officio.”
“It had no endowment, but owned a fine piece of property consisting of grounds and six buildings … at Kaimukī near Waiʻalae Bay, a mile from the end of the Waiʻalae street-car line.” (DOI Bureau of Education Bulletin 1920)
“The school drew its cadets from all points in the islands. The 1918-19 roster showed 64 from Honolulu, 10 from Oʻahu outside of Honolulu, 16 from Hawaiʻi, 11 from Maui, 10 from Kauaʻi, 1 from Molokai, 2 from California, and 1 each from New York State, Minnesota, and Japan.”
“It began at first with instruction only in the elementary grades; but it grew to offer a 12-grade program of studies.” (DOI Bureau of Education Bulletin 1920)
Then, in January 1925, Punahou School bought the Honolulu Military Academy property – it had about 90-acres of land and a half-dozen buildings on the back side of Diamond Head.
It served as the “Punahou Farm” to carry on the school’s work and courses in agriculture. “We were picked up and taken to the Punahou Farm School, which was also the boarding school for boys. The girls boarded at Castle Hall on campus.” (Kneubuhl, Punahou) The farm school was in Kaimukī between 18th and 22nd Avenues.
In addition to offices and living quarters, the Farm School supplied Punahou with most of its food supplies. The compound included a big pasture for milk cows, a large vegetable garden, pigs, chickens, beehives, and sorghum and alfalfa fields that provided feed for the cows. Hired hands who tended the farm pasteurized the milk in a small dairy, bottled the honey and crated the eggs. (Kneubuhl, Punahou)
The Punahou dairy herd was cared for by the students as part of their course of studies – the boys boarded there. However, disciplinary troubles, enrollment concerns (not enough boys signing up for agricultural classes) and financial deficits led to its closure in 1929.
By the mid-1930s, the property was generally idle except for some Punahou faculty housing. In 1939, Punahou sold the property to the government as a site for a public school (it’s now the site of Kaimuki Middle School.) The initial Aliʻiolani College site is the present site of Aliʻiolani Elementary School.)
The image shows the original Aliʻiolani building, funded by Mary Foster (Maui News, July 30, 1910.) In addition, I have added other related images in a folder of like name in the Photos section on my Facebook and Google+ pages.