In 2010, Castilleja received a bequest from alumnae parent and former Trustee Bill Halford that was used to found the Halford Young Women Leaders' Program (HYWLP). Based on a well-established curriculum developed at the University of Virginia, the program connects motivated middle school girls from local under-resourced communities and Castilleja Upper School students through a year-long mentoring curriculum. According to Sophie Levin ’13, Halford Big Sister and Curriculum Development Intern, “the curriculum focuses on how to prepare young women to be leaders through group activities, community engagement and service projects, and student-initiated programs all designed to build skills and self-confidence.”
Throughout the academic year, the high school and middle school big and little “sisters” meet weekly to support one another in the development of leadership skills. A leadership curriculum, community engagement and service projects, and student-initiated programs, help each girl develop skills for success and a stronger belief in her own capacities. Together, big and little sisters support one another in learning strategies to reach their goals, establish support networks, and constructively pursue their interests within the community. Their development of essential life skills and deeper self-esteem, is complemented by the cultivation of lasting bonds of friendship and trust.