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The school was founded in 1854 by David Austin Sayre for the education of young women.
In the fall of 1855 the school was moved to its current location on Limestone Street (see the National Register of Historic Places information about the expansion of the original building), and the trustees changed the name to the Sayre Female Institute.
In fact, during this tumultuous time future Kentucky suffragist Laura Clay enrolled in the institute in the fall of 1863.
Clay was at the school in June 1864, when General John Hunt Morgan and his Confederate cavalry held Lexington for a short period of time.
Sayre believed that women deserved an “education of the widest range and highest order.” Originally named Transylvania Female Institute, the school was renamed in honor of Sayre in 1885.
During the Great Depression, the school struggled, but in 1942 it grew with the incorporation of the Hamilton Grammar School, and changed its name to Sayre School, dropping its collegiate degree program.
In 1961 an English teacher from Lafayette High School, Donn D. Hollingsworth was appointed headmaster and the high school was resumed in addition to the grammar school, beginning the "New Era."
In 2002, the symposium was named in memory and honor of its founder and director, F. Kevin Simon.
2020 F. Kevin Simon History Symposium
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| Company name | Founded date | Revenue | Employee size | Job openings |
|---|---|---|---|---|
| Charlotte Christian School | 1950 | $50.0M | 154 | 1 |
| Rutgers Preparatory School | 1766 | $50.0M | 100 | - |
| University School of Jackson | 1987 | $50.0M | 100 | - |
| North Cross School | 1941 | $10.0M | 100 | 1 |
| Roycemore School | 1915 | $10.0M | 125 | - |
| Charlotte Preparatory School | 1971 | $10.0M | 20 | - |
| Lancaster Country Day School | 1909 | $50.0M | 100 | - |
| Westminster Schools Of Augusta | 1972 | $4.5M | 55 | 9 |
| Bridgeport International Academy | 1997 | $999,999 | 20 | - |
| Ware Academy | 1949 | - | 27 | - |
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Sayre School may also be known as or be related to SAYRE SCHOOL and Sayre School.