Caroline High School
ACADEMIES OF CAROLINE
Administration:
Dr. Thomas Connolly, Principal
- Robert Dudley, Assistant Principal
- Melissa Frye, Assistant Principal
- Dr. Jaime Harnden, Assistant Principal
- Joshua Williams, 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
Welcome to Cavalier Nation
Together, we are building 3E-ready Cavaliers—prepared to be Enrolled, Employed, or Enlisted and ready to create a bright future.
Explore Student-Created Podcasts from Caroline High School
Student voices. Fresh ideas. Something for everyone. Explore CPN, the Caroline High School Podcast Network, where students show off their hard work, interests, and perspectives—one episode at a time.
Cavalier Events
Senior Night & Black Out: November 5!
It’s SENIOR NIGHT and a BLACK OUT, Cavalier Nation! Wear all black to school November 5, then cheer on your Cavaliers against Culpeper County at 7:30 p.m. in our final home football game!
2026 Quarter 1 Parent-Teacher Conferences
Caroline High School Parent-Teacher Conferences are coming up on November 3rd from 11:00-7:00. Open this post for the scheduling link.
Cavalier Spotlight
Student of the Month – Iriellah Arbitrario
Congratulations to Iriellah Arbitrario, Caroline High School’s Student of the Month for October!