Rebecca Greenleaf Clapp

head of school

Becky attended Milton Academy, earned a Bachelor's degree from Smith College, and a Master's from Brown University. She developed programs for second and fourth graders for Milton's A.P.P.L.E. (A Personally Planned Learning Experience) Summer Program for 10 years, and taught Cultural Studies to sixth through eighth graders at the Foundation School in Orange, Connecticut. Becky served on the Head’s Council at Milton Academy, the Board of Trustees of St. Mark’s, and the Seth Sprague Educational and Charitable Foundation. She has served as a representative to educational associations including, Independent Schools of Northern New England, Independent Schools of Mid-Coast Maine, and PIN (Parents in Independent School Network).

In 2011, Becky launched her own business, Greenleaf Educational Consulting, organizing secondary school fairs for the mid-coast region and supporting families in their search for the best independent schools. Starting in 1988, Becky has worn many hats at the Riley School, including parent, Lower School Facilitator, Development Director, Trustee, and currently as Head of School.