Caroline High School
Administration:
- Dr. Thomas Connolly, Principal
- Robert Dudley, Assistant Principal
- Melissa Frye, Assistant Principal
- Dr. Jaime Harnden, Assistant Principal
- Dr. Natasha Smith, Assistant Principal
- 19155 Rogers Clark Blvd Milford VA 22514
Hours of Operation:
7:00 AM – 3:30 PM
Class Hours:
7:30 AM – 2:35 PM
Registration by appointment
8:00 AM – 2:00 PM
Telephone:
Tel: (804) 633-9886
To the Cavalier Nation,
My name is Tom Connolly, and I am thrilled to serve as the principal of Caroline High School. My goal is to support our dedicated teachers and staff in educating every student to become 3E Ready: prepared for Enrollment in a two-year or four-year college or vocational program, Enlistment in the military, or Employment in a career path. The CHS Leadership team, counselors, and teachers will work diligently to ensure our students have access to a world-class education and take pride in being Caroline Cavaliers.
As a father of two middle schoolers and one elementary schooler, I understand the importance of parents feeling supported. The faculty and staff at Caroline High School are committed to partnering with you to support the success of your child. I believe that high-quality student learning is essential to preparing students for life after graduation, and this quality is enhanced through building and maintaining an open, honest, and productive partnership with parents.
As we prepare for this school year, I encourage every CAV to demonstrate respect, responsibility, and honesty in all their actions—whether in the classroom or participating in extracurricular events or competitions, CAVS will CHOOSE GREATNESS In everything they do. Through engaging academic experiences and a competitive atmosphere in extracurriculars, I want each CAV to develop Confidence in their abilities, be Accountable for their learning and success, and build a Vision for what they want to achieve before and after graduation.
Please do not hesitate to email me at tconnolly@ccps.us or call me at (804) 633-9886 if you have any questions or concerns. I appreciate your time and thank you for helping CHS reach our goal of all Cavaliers Learning Today and Leading Tomorrow!
Sincerely,
Tom Connolly
Principal

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Cavalier News & Events

Governor’s & Lab School Information Night
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2025-26 Yearbook Orders Are Now Open!
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Black History@ Your Library
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Cavalier Nation News
Select the link below to read the February edition of the Cavalier Nation News. February 2023
Congratulations, Cavalier Track and Field!
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CHS Rules the Cavalier Clash
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