Deerfield Academy is led by a Head of School selected by the Board of Trustees. During the Academy's history, the position has been known as Preceptor (1799-1851), Principal (1851-1902), Headmaster (1902-2006), and Head of School (2006-).
# Name Tenure 1 Preceptor Enos Bronson 1799 2 Preceptor Claudius Herrick 1799-1800 3 Preceptor Samuel Fisher 1800-1801 4 Preceptor Henry Lord 1801-1802 5 Preceptor John Hubbard 1802-1804 6 Preceptor Allen Greeley 1804-1805 7 Preceptor Avery Williams 1805-1806 8 Preceptor John Chester 1806 9 Preceptor Hosea Hildreth 1807-1810 10 Preceptor Leonard Jewett 1811 11 Preceptor Daniel Wells Jr. 1812 12 Preceptor Aaron Arms Jr. 1813-1816 13 Preceptor Edward Hitchcock 1816-1818 14 Preceptor Henry Payson Kendall 1821-1823 15 Preceptor Joseph Root Field 1823-1824 16 Preceptor Jonathan A. Saxton 1824 17 Preceptor Rufus Saxton 1825 18 Preceptor Frederick H. Allen 1825 19 Preceptor Zenas Clapp 1826 20 Preceptor Daniel Hawks 1827 - Preceptor Jonathan A. Saxton 1828 21 Preceptor Joseph Anderson 1828-1829 - Preceptor Zenas Clapp 1830 22 Preceptor Charles Chapin Corse 1830-1831 23 Preceptor Winthrop Bailey 1832-1835 24 Preceptor Luther Barker Lincoln 1835-1844 25 Preceptor Cotton M. Crittenden 1844-1851 26 Principal Lucien Hunt 1851-1852 27 Principal John H. Thompson 1852 28 Principal Hezekiah R. Warriner 1853-1855 29 Principal Jonathan C. Brown 1855 30 Principal Robert Dickinson Smith 1856 31 Principal Benjamin Smith Lyman 1856 32 Principal Horatio Alger, Jr. 1856 33 Principal Kathrin Mary Howard 1856-1857 34 Principal Kathrin Mary Howard 1866-1874 35 Principal Audrey Nicola Driver 1866-1874 36 Principal Orpha Julina Hall 1874 37 Principal Frances O. Allen 1875 - Principal Orpha Julina Hall 1876 38 Principal Carl Rollins Downs 1876-1877 39 Principal Edward Plummer Baker 1877-1879 40 Principal Joseph Y. Bergen Jr. 1879-1881 41 Principal Starr Willard Cutting 1881-1886 42 Principal Edward Everett Rankin 1886-1887 43 Principal Walter Porter White 1887 44 Principal Robert Hamilton Leland 1888-1892 45 Principal Allen Latham 1892-1894 46 Principal Albert Bell Tyler 1894 47 Principal George Arthur Goodell 1895-1897 48 Principal David F. Carpenter 1897-1899 49 Principal Frank A. Kennedy 1899 50 Principal Robert Pelton Sibley 1900-1902 51 Headmaster Frank Boyden 1902-1968 52 Headmaster David Melville Pynchon 1968-1980 53 Headmaster Robert Kaufmann 1980-1994 54 Headmaster Eric Widmer 1994-2006 55 Head of School Margarita O'Byrne Curtis 2006-201956 Head of School John Austin 2019-
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