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

Click here for our amazing student podcasts!
Browse and select any number of our fabulous student-run podcasts,
produced by Mass Media and ready to stream!
Cavalier News & Events
UPCOMING FALL ATHLETIC EVENTS @ CHS
Monday – 10/24 – Volleyball hosts Eastern View HS with JV playing at 6 pm followed by Varsity at 7:15 am. Wednesday – 10/26 –
Boys Cross Country 4th in Battlefield Championship
Boys’ cross country finished 4th in the Battlefield Championships this past week. Elijah Kessler and Anton Jones both had top 15 finishes.
CHS PTSO Meeting 11/10 @ 6 PM
WHEN THURSDAY, NOV. 10TH, 6PM WHERE CAROLINE HS LIBRARY For this school year, the CHS PTSO will conduct meetings the second Thursday of every month
School Couseling Updates
The Counseling Newsletter for October is now live. Click here Seniors remember to see your College and Career Advisors to get your plan for life after
CHS PTSO Meeting 10/13
THURSDAY, OCT. 13TH, 6PM For this school year the CHS PTSO will conduct meetings the second Thursday of every month at 6 pm in the
CHS Parent/Teacher Conferences
WHEN THURSDAY, OCT. 13TH, 3-6PM Teachers and staff will be available for in-person or virtual conferences Thursday, 10/13/2022, from 3 to 6 pm. If you
LITERACY FESTIVAL
The CCPS PK–12 Literacy Festival takes place on Wednesday, November 15, 2022, from 5:30–7:00 p.m. at Caroline Middle School. All students in grades PK–12 are
PSAT DAY @ CHS
WHEN WEDNESDAY, OCT. 12TH, 7:30AM The PSAT will be given here at CHS on October 12th only for all CHS 10th grade students and 11th
Dual Enrollment Open House
SAVE THE DATE • VIRTUAL EVENT Dual Enrollment Open House For rising high school and home school juniors, seniors, and their families October 18 • 6 p.m. Learn
FAFSA NIGHT 2025
WHEN TUESDAY, OCT. 21ST, 2025 at 5:30 PM WHERE CAROLINE HIGH SCHOOL The FAFSA (Free Application for Federal Student Aid) opens on October 1st! It
STUDENT OF THE MONTH – MALACHI DRUMGOLE
Malachi Drumgole, son of Lisa Drumgole, was selected as Student of the Month for September at Caroline High School. Malachi was selected by his teachers
CHS Band Takes Top Honors
The CHS Marching Band earned a 2nd place in percussion, color guard, general effect, visuals, music, and they earned a 2nd place overall finish this
UNDERCLASSMEN PICTURES (GRADES 9-11)
WHEN THURSDAY, SEP. 22ND, 7:45AM Underclass pictures (9th -11th) will take place on 9.22.22 in the CHS auditorium.
COLLEGE INFORMATION MEETINGS FOR JUNIORS AND SENIORS
If you are a junior or a senior and are interested in attending a college visit from one of the following colleges or universities, please
CHS COUNSELING INFORMATION
Here is the link to a scholarship list that will be continuously updated throughout the year: CHS Scholarship Information 22-23 Contact Ms. Shortridge or Mrs. Hummer if