Caroline High School Alumni
Milford, Virginia (VA)
Recent Members
| Caitlyn Ennis | 2011 |
| Clayton Boling | 2018 |
| Heidi H Dann Heidi H Dann | 1993 |
| Juanita Johnson | 1993 |
| Lakisha Marshall | 2009 |
| Samuel Merrell | 2023 |
| Shontae Derricott | 2005 |
| Tiffany Tiffany Allen | 2010 |
Military Alumni
Honoring Our Heroes
This area is dedicated to our alumni that have served or are serving in our armed forces!
Lost Class Rings
Have you lost your Caroline High School class ring? Have you found someone's class ring? Visit our Cavaliers lost class ring page to search for your class ring or post information about a found ring.
Honored Military Alumni
Cory Fortune
Class of 1998
Army, 8 Years
Stationed at Ft lewis, Washington. Served in Afghanistan from 2002-2003. Currently with the 160th SOAR (A), serving as Tech Supply Logisticians.
Class of 1998
Army, 8 Years
Stationed at Ft lewis, Washington. Served in Afghanistan from 2002-2003. Currently with the 160th SOAR (A), serving as Tech Supply Logisticians.
Darrel Simpkins
Class of 1992
Army, 15 Years
Stationed at Fort Stewart, Germany, Fort Bragg, & Fort Rucker
Deployed to Bosnia(96-2000), Bahamas(94-96), and Iraq(2005)
Class of 1992
Army, 15 Years
Stationed at Fort Stewart, Germany, Fort Bragg, & Fort Rucker
Deployed to Bosnia(96-2000), Bahamas(94-96), and Iraq(2005)
dayle sampson
Class of 1983
National Guard, 1 Years
13 bravo field artillery, and 54 echo nuclear, biological, chemical warfare expert
Class of 1983
National Guard, 1 Years
13 bravo field artillery, and 54 echo nuclear, biological, chemical warfare expert
Dennis Harless
Class of 1980
Marine Corps, 20+ Years
Career Marine, retired as a 1st Sgt in 2000
Class of 1980
Marine Corps, 20+ Years
Career Marine, retired as a 1st Sgt in 2000
Dona Gage
Class of 2003
Air Force, 4 Years
Basic Training Lackland AFB, TX
Tec School Ft. Meade MD>
Stationed at Langley AFB, Va
Current Sqaudron 36 Intelligence Squadron
Class of 2003
Air Force, 4 Years
Basic Training Lackland AFB, TX
Tec School Ft. Meade MD>
Stationed at Langley AFB, Va
Current Sqaudron 36 Intelligence Squadron
Jacqueline Olivia Chaplin
Class of 1965
Army Reserves, 20+ Years
Retired Dec 2007 as MSG. Retention NCO.
Class of 1965
Army Reserves, 20+ Years
Retired Dec 2007 as MSG. Retention NCO.
jeremy frye
Class of 2001
Army, 4 Years
assigned 173rd airbonre brigade, Vicenza, Italy. Iraq 2003-2004. Scout/sniper, Afghanistan 2005-2006. Married to Aleche Benale of Vicenza.
Class of 2001
Army, 4 Years
assigned 173rd airbonre brigade, Vicenza, Italy. Iraq 2003-2004. Scout/sniper, Afghanistan 2005-2006. Married to Aleche Benale of Vicenza.
John Galimore
Class of 1982
Army, 20+ Years
Retired U.S. Army Chief Warrant Officer
Class of 1982
Army, 20+ Years
Retired U.S. Army Chief Warrant Officer
Larry Cutler
Class of 1991
Navy, 4 Years
Served onboard the USS AMERICA CV-66 DURING OPERATION SUPPLY HOPE /BLACKHAWK DOWN
Class of 1991
Navy, 4 Years
Served onboard the USS AMERICA CV-66 DURING OPERATION SUPPLY HOPE /BLACKHAWK DOWN
Phillip W. Parker
Class of 1984
Army, 4 Years
U.S. Army Jump School, May 1986 82nd Airborne 1st/504th Parachute Infantry Regiment 86-89. Operation Golden Pheasant, Honduras 1988. Award for Meritorious Heroism. Jungle Expert School Ft Sherman Panama, 1987.
Class of 1984
Army, 4 Years
U.S. Army Jump School, May 1986 82nd Airborne 1st/504th Parachute Infantry Regiment 86-89. Operation Golden Pheasant, Honduras 1988. Award for Meritorious Heroism. Jungle Expert School Ft Sherman Panama, 1987.
Sean Kittle
Class of 2006
Army, 1 Years
U.S. Army Contract at The Citadel, South Carolina Corps of Cadets. Officially a member of the U.S. Army as of 10/10/2006, commissioning 05/2010
Class of 2006
Army, 1 Years
U.S. Army Contract at The Citadel, South Carolina Corps of Cadets. Officially a member of the U.S. Army as of 10/10/2006, commissioning 05/2010
Stacie Perkins (Brooks)
Class of 1998
Marine Corps, 8 Years
Served at Marine Corps Air Station Cherry Point in North Carolina. VMAT-203 S-4...Embarkation and Logistics Combat Support Specialist
Class of 1998
Marine Corps, 8 Years
Served at Marine Corps Air Station Cherry Point in North Carolina. VMAT-203 S-4...Embarkation and Logistics Combat Support Specialist
Thaddeus Allen
Class of 2002
Army, 2 Years
Stationed in Fairbanks, Alaska with the 172nd Stryker Brigade. Currently serving in Baghdad, Iraq.
Class of 2002
Army, 2 Years
Stationed in Fairbanks, Alaska with the 172nd Stryker Brigade. Currently serving in Baghdad, Iraq.
Alumni Stories
Read and submit stories about our classmates from Caroline High School, post achievements and news about our alumni, and post photos of our fellow Cavaliers.
School News
Renovations at CHS
If you are not a frequent flyer at our alma mater, stop in and check out the library. They spent the summer renovating,...
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Our Caroline High School military alumni are some of the most outstanding people we know and this page recognizes them and everything they have done! Not everyone gets to come home for the holidays and we want our Caroline High School Military to know that they are loved and appreciated. All of us in Milford are proud of our military alumni and want to thank them for risking their lives to protect our country!