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 Scarborough Historic District is a national historic district located in the suburban community of Scarborough-on-Hudson, in Briarcliff Manor, New York. The 376-acre (152 ha) district was added to the National Register of Historic Places in 1984, and contains seven historically and architecturally significant properties dating from the late 18th century to the early 20th century. Most of the properties are domestic, or used for education or religion. The most common architectural styles within the district are Mid-19th Century Revival and Late Victorian.