Bessie Speers – Head of School

Elizabeth “Bessie” Cromwell Speers officially began her tenure as Middlesex’s seventh head of school on July 1, 2023, bringing more than 30 years of experience in independent schools to the position. Previously, she served for eight years as the head of Tower Hill School in Wilmington, Delaware; her first headship was at The Ethel Walker School in Simsbury, Connecticut, where she served from 2007 to 2015. Bessie’s prior experience also includes serving as assistant head of school, dean of faculty, English teacher, and coach at Episcopal Academy near Philadelphia; director of placement and strategic planning at Calvert School in Baltimore; director of admission and financial aid, teacher, and coach at The Bryn Mawr School in Baltimore; and associate director of admission, coach, and adviser at The Loomis Chaffee School in Connecticut. She began her career working with the National Association of Independent Schools (NAIS).

Bessie has long been familiar with Middlesex through her husband Tom, a Presbyterian minister who graduated from the School in 1976. A graduate of The Bryn Mawr School, Bessie holds a B.A. in English from Middlebury College and an M.L.A. from Johns Hopkins University; she also studied at Middlebury’s Bread Loaf School of English. She received a Klingenstein Fellowship at Columbia University’s Teachers College in 2014 and has been active with various professional organizations, including the Connecticut Association of Independent Schools, The Center for Spiritual and Ethical Education, and The National Coalition of Girls’ Schools, as well as The Heads Network and The Heads and Principals Association, both of which she served as president. Bessie served on the board of the Association of Delaware Valley Independent Schools (ADVIS) and is currently a trustee of Middlebury College.