Holbrook Military Academy
Dr. Holbrook's Military School, c. 1900
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| Type | Private |
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| Active | 1864–1915 |
| Location | Briarcliff Manor, New York |
| Campus |
25 acres (10 ha) |
 Holbrook's Military School
Location of Dr. Holbrook's Military School
Holbrook's Military School
Location of Dr. Holbrook's Military School
Holbrook's Military School
Location of Dr. Holbrook's Military School
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| Coordinates | 41°09′11″N 73°51′01″W / 41.152944°N 73.850194°WCoordinates: 41°09′11″N 73°51′01″W / 41.152944°N 73.850194°W |
25 acres (10 ha)
Dr. Holbrook's Military School was a military academy and boarding school for boys. The school was located in the town of Ossining and overlooked the Hudson River. After the 1906 annexation of Scarborough by the village of Briarcliff Manor, Holbrook's became part of the village within Ossining.
The school was founded in 1864 as Mr. Tracy's School. In 1866, after David A. Holbrook purchased the school, it became known as Dr. Holbrook's Military School. The school ran until 1915, after which it was used in World War I as a field hospital and headquarters to a New York Guard regiment. From 1919 until at least 1927, the school served as the Teachers College Country Club.
Saint Denis Institute was said to have occupied the land prior to the school. It was founded in 1864 as Mr. Tracy's School, a seminary for young women on a 10-acre (4.0 ha) estate. In 1866, Reverend David A. Holbrook, PhD, purchased the school and turned it into a boys' school and enlarged it to 25 acres (10 ha), and it had 60 students.
After Holbrook's death in December 1898, Dr. Holbrook's sons Dudley and Henry became involved with running the school. They were joined in 1899 by their brother Dwight, and ran the school until its closure as Holbrook's Preparatory School for Boys. When it closed in 1915 the school had 80 students.
Shortly after the school's closure, in 1917, events in World War I had led the New York Guard's First Provisional Regiment (1,500 men operating under Colonel John B. Rose) to guard the Croton Aqueduct. Captain Charles W. Baldwin, Chaplain of the regiment and Rector of Saint Mary's Episcopal Church in Scarborough and also in present-day Briarcliff Manor, had arranged a deal with V. Everit Macy, then the owner of the school estate, for free use of the campus and buildings for until three months after the war's end.
The regiment, originally headquartered at Pines Bridge Inn on Croton Lake, moved its headquarters to the Holbrook Military Academy, and the academic building at the school became Field Hospital No. 2 of the Atlantic Division of the American Red Cross. The ground floor of the west wing and the mess hall on the first floor was turned into a large, well-heated office with glass-partitioned private offices, and equipped with typewriters and mimeograph machines. The new regimental office had strong contrast with their Pines Bridge Inn office, it having been drafty, dirt-floored and poorly-lit. The site opened for their use on October 8, 1918, and the regiment fully demobilized on February 1, 1919. A reunion was held at the former school grounds for many of the troops from March 23 to 25, 1919.
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