| The Milton Academy Heads of School |
| Milton Academy's ten most
recent Headmasters. Unfortunately, the Milton Academy archives do
not include a picture of Milton's first head, Samuel Thurber |
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| Samuel Thurber, Prinicipal
1885–1887 |
Harrison Otis
Apthorp, Prinicipal and Headmaster 1887–1904 |
Richard Cobb,
Headmaster 1904–1910 |
Frank Edwin
Lane, Headmaster 1910–1917 |
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| William Lusk
Webster Field '94, Headmaster 1917–1942 |
Cyril Hamlen
Jones, Headmaster 1942–1947 |
Arthur Bliss
Perry, Headmaster 1947–1963 |
David Douglas
Wicks, Headmaster 1963–1973 |
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| Jerome A. Pieh,
Headmaster 1973–1991 |
Edwin P. Fredie,
Headmaster 1991–1999 |
Robin Robertson,
Head of School 1999–2007 |