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The school opened on September 12, 1899, with 40 students, half of whom were boarders.
The Massanutten Military Academy, named for the nearby mountain, was established by the Virginia Classis of the Reformed Church in 1899.
From the beginning the school was coed, with the first graduating class in 1902 consisting of three boys and three girls.
In 1905, the first of two significant events in the history of the school occurred: Howard J. Benchoff was appointed the school president.
The second, as a result of an otherwise undocumented "incident", was limiting the boarding department to boys beginning in 1910.
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| Company name | Founded date | Revenue | Employee size | Job openings |
|---|---|---|---|---|
| Randolph-Macon Academy | 1892 | $50.0M | 200 | - |
| Florida Air Academy | 1961 | $8.9M | 71 | - |
| Hargrave Military Academy | 1909 | $50.0M | 100 | - |
| Cushing Academy | 1865 | $79.7M | 160 | 14 |
| Brandon Hall School | 1959 | $10.0M | 50 | - |
| Girard College | 1848 | $9.8M | 350 | - |
| Brewster Academy | 1820 | $50.0M | 468 | 4 |
| The Derryfield School | 1964 | $50.0M | 105 | - |
| Gunston Middle School | - | $11.0M | 350 | - |
| Grace Academy-Hartford | 2010 | $999,999 | 30 | - |
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