The story of retired Captain Charles A. Ramsey II begins at the home where he grew up in High Point, North Carolina. He and his family refer to it as “Pennywood.”
Pennywood is not just a house, it’s more of a private grounds. Charles II and his sisters, Melanie and Robin were raised there. His parents, Charles Senior and Gloria designed the house themselves, and today, Charles Senior still lives there. Sadly, Gloria passed away in 2015. But her presence is still greatly felt at Pennywood. It remains a metaphorical place of peace and unity for the entire Ramsey family.
Charles Senior was the first to serve in the military. He was in the Signal Corps in the Army, and he served at Camp Polk for several years. Charles II’s younger sister Robin was the next to enlist. During college, she joined the Army Reserve Officers' Training Corps (ROTC) program, but Charles II was first introduced to the ways of the Army in military school.
Oak Ridge Military School
It was at Oak Ridge Military School that Charles II began to develop an understanding of the bigness of the world, and how to literally play his part. He became the bugler – the first up in the morning, responsible for sounding the bugle to wake the rest of the residents and dictate the chosen uniform of the day. Sounds rough. But there was an upside – he got to eat first.
“It’s amazing that my parents found a place for me to go to a school that tied right into what I was already ingrained with and exposed to,” Charles said. “I went to school with kids from all around the world. And Oak Ridge prepared me for the military. I got used to a structured environment.”
Enlisting in the Army
After Charles graduated from Oak Ridge, he felt the pressure many of us did, to go straight into college. It didn’t take long to realize a typical college environment wasn’t the right fit for him. He had his sights set on joining the Army, just as his sister had before him. Telling his highly-educated mother? Not so simple.
“Imagine coming home and telling a woman who has two undergraduate degrees, seven Master's degrees, and two PhDs that you want to drop out of college. It wasn’t a pleasant conversation in the beginning,” he said.
In 1992, his sister, Captain Robin Ramsey, enlisted him into the U.S. Army as a Private First Class. Basic training started in Fort Sill, Oklahoma in May. And the journey began.
Sights Sets on a Black Hawk
After basic training, Charles II was stationed in Fort Hood, Texas, where he started out as an Avenger Crew Member, manning the turret on a Humvee chassis that fired stinger missiles. For the next 23 years, he would work to move up the ranks and was stationed all over the map. We’ve included a full list of his military service at the bottom of this story.
On a somber day in 1993, Charles II was attending a service at an aviation hangar to honor an Army pilot who had tragically lost his life. It was there that he first saw a Black Hawk helicopter in person. Since he was a little boy, Charles II had always been intrigued by the idea of being a pilot. The Black Hawk’s pilot was standing nearby, so Charles II asked him, “What does it take to go to flight school?” The soldier replied, “Ah, don’t worry about it, you could never fly one of these.” Charles was taken back. But the principles his parents had instilled in him – to always go after your dreams – immediately kicked in. Then and there, he decided he would become a Black Hawk pilot.
After one of the most devastating days in U.S. history, September 11, 2001, Charles was deployed to Afghanistan and served in a special task force. It was an eye-opening experience for him. “We don’t realize sometimes the simple things that other countries don’t have, and it’s unfortunate, but when you get to see it from that perspective, it really gives you a whole new vision on what we have,” he said. “I’ve been in so many situations in countries where people who have so little are so humble and so nice.”
During his deployment to Afghanistan, with every moment of downtime he had, Charles studied for the pilot’s exam. He even enlisted some pilots to help quiz him. And as soon as he returned home from Afghanistan, he took the flight test and passed it.
“My parents always told me, to never let anyone tell you that you can’t; don’t let anything get in your way of stopping you from accomplishing a goal that you’ve set,” Charles recounted.
In 2004, after Charles II graduated from Flight and Warrant Officers School, he returned to the place where it all began–where the pilot told him he never would fly a Black Hawk–Fort Hood, Texas. And in 2004 he would be deployed again to Iraq and Afghanistan, only this time, as a Black Hawk Pilot and Medivac.
“I always wanted to be able to carry troops around and that’s really how I gravitated towards flying Black Hawks.” Charles II said. But he didn’t just fly the troops. He flew dignitaries, congresswomen, senators, journalists, and even Army generals. As for that pilot that told him he would never fly a Black Hawk? Well, he didn’t know how much determination Charles Senior and Gloria Ramsey had instilled into their children.
In 2015, it was as if a switch had flipped. Charles II decided it was time to retire. After 23 years of active duty in the U.S. Army, he was done. He’d managed to get his Bachelor’s degree and a Master’s and would be retiring as a Captain. It was time for a whole new adventure. So, at the close of 2018, Charles II decided to take on a new cockpit – he had his eye on a 2019 Tiffin Open Road Allegro 34PA.
Life on the Open Road
Today, Charles II is out there on the open road, taking in the beauty of the country he served for 23 years from the ground level instead of the sky. He’s manning his new cockpit – the Tiffin Open Road Allegro, and occasionally, he’s even closer to the pavement on his custom Harley Davidson motorcycle.
“I have a homegrown motorcoach that’s made right here in the good old U.S. of A., and that, hands-down means a lot,” he said.
Sometimes, he’s got his long-time best friend Fred Wright by his side, listening to music from the impressive sound system Fred installed for him. Other times, it’s family. And on occasion, he’s traveling to festivals or music video shoots with the up and coming R&B musician he now manages, QB Smith.
He met QB Smith in the Austin music scene while stationed in Fort Hood. The new friendship relit his life-long passion for music. Now that Charles II has a motorhome with all the amenities they could possibly need, they can easily travel together to festivals where QB Smith performs, and recently, they drove out to Texas to film a video for the upcoming song off his album called “Silver Wings.” But music is just one of the many adventures Charles II has been able to embark on since retirement.
He loves to take his time traveling across the country, stopping at as many RV Campsites as he can, each one with a new crowd of welcoming motorhome enthusiasts just like himself. And, of course, he has a bucket list of places he wants to hit. “I want to get out and see the California redwoods while they’re still standing. And one day, I want to be able to travel the original Route 66 and see what’s there.”
But what he really enjoys is the freedom to stop anywhere, anytime he wants.
“On the way back from the Essence Music Festival, I just decided to make a detour off to Montgomery to go to The National Memorial for Peace and Justice museum, which was really cool. I saw a sign and said, “Oh, Montgomery, 82 miles.”
Here’s the full picture of Charles II’s 23 years serving in the U.S. Army.
1992 - Fort Sill, OK - Basic training
1992 - Fort Bliss, TX - Advanced Individual training, Avenger Crew Member
1992 - Fort Hood, TX - Manned the turret on a Humvee chassis that fired stinger missiles
1993 - Fort Hood, TX - Selected to 1st Cavalry Division Honor Guard
1995 - Germany - Selected to serve as Driver of Division Commander Major General Montgomery C Migs
1998 - 2001 - Greensboro, NC - Recruiting Duty
2001 - 2002 - Deployed to Afghanistan; Fort Drum, NY - Avenger Crew Member; Task Force 187
2003 - Fort Rucker, AL - Graduated Flight School & Warrant Officers School
2004 - Fort Bragg, NC - Deployed to Iraq and Afghanistan; Pilot & Medivac
2008 - Fort Benning, GA - Graduated from Officers Candidate’s School & commissioned to 2nd Lieutenant
2008 - 2012 Fort Hood, TX - Promoted to 1st Lieutenant & Captain, Black Hawk Pilot
2009 - 2010 - Deployed to Iraq & promoted to 1st Lieutenant
2011 - Deployed to Afghanistan
2012 - Fort Lee, VA - Attended Captain’s Career Course
2013 - 2015 - Fort Bragg, NC - Logistics Operations Officer in 528th Sustainment Brigade, Special Operations
2014 - Fort Bragg, NC - Selected to serve as Commander of Bravo Company Special Warfare Training Center