In 1984, the Rappaport Family established an endowed award fund for faculty named in honor of The Winsor School’s longest tenured Director, Virginia Wing. The family educated six daughters at the school and wanted to honor its outstanding educators. The Virginia Wing Outstanding Teacher Award is presented annually at graduation to a teacher, selected by the senior class, who by his or her teaching skills, inspiration, devotion, befriending or counseling has best served the student body in the Winsor tradition. Throughout the decades since its inception, the award provides meaningful recognition to the school’s most devoted teachers, and has become a much-cherished tradition.