List of heads of Deerfield Academy
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- |
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