DOCTOR HOLBROOK’S MILITRY ACADEMY

Dr. Holbrook's Military Academy was a military academy and boarding school for boys. It 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 Briarcliff Manor.

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. After Holbrook's death in December 1898, his sons Dudley and Henry ran the school. In 1899 their brother Dwight joined them and together they ran the school until its closure in 1915 as Holbrook's Preparatory School for Boys. At its close the school had 80 students.