The 3 Best School Principals Around Winchester

School principals play a central role in shaping the culture, performance and day-to-day experience of students and staff. In the Winchester area, principals guide everything from academic priorities to school climate, often balancing administrative leadership with direct community engagement. Their influence extends beyond the classroom, impacting extracurricular programs, family relationships and long-term student outcomes. Recognized in the Star Awards, these leaders reflect the range of approaches used across Frederick County to support student success at every level.

Karen McCoy | Sherando High School

Karen McCoy serves as principal of Sherando High School, bringing more than a decade of experience from her previous role as assistant principal at the same campus. Her leadership emphasizes continuity and stability, supported by her familiarity with the school’s staff and student population of more than 1,600. She promotes a balanced environment that supports intellectual, emotional and social development within a structured setting. Through a collaborative approach often described as the “Powhatan way,” she focuses on strengthening connections among faculty, students and the broader school community.

Jamal Womble | Evendale Elementary School

Jamal Womble leads Evendale Elementary School, overseeing early education programs for nearly 600 students. His administration prioritizes foundational skills such as literacy and social-emotional development, aligning with broader district goals. He works closely with staff and families to maintain a consistent and supportive learning environment. By emphasizing communication and collaboration, he helps create a setting where students can build strong academic and social foundations.

Jerry Cave | Rhodes Alternative Education Program (John Handley High School)

Jerry Cave administers the Rhodes Alternative Education program associated with John Handley High School, focusing on students who benefit from a non-traditional learning structure. His role centers on individualized instruction and behavioral support, helping students stay on track toward graduation. The program provides flexibility while maintaining connections to the larger school system. Through targeted interventions and close coordination with staff, he supports students navigating unique academic and personal challenges.

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