This article was originally published by The Bluffton-Hilton Head Sun.
By Paul Tollefson
This is one of those stories where you realize Hilton Head didn’t just grow, it was guided there by people who believed in its future long before anyone else did.
Back when the island moved to the rhythm of the tides, when dirt roads cut through oak and pine and the schoolhouse sat at the heart of the community, two educators arrived with a simple purpose, to teach and to serve. Mr. Isaac and Ramona Wilborn didn’t just take jobs on Hilton Head, they became part of its foundation.
In 1954, when the island’s elementary school needed both a principal and a teacher, the Wilborns stepped in. Isaac became the steady hand leading the school, helping shape it into something far greater than a building. For nearly three decades, he guided generations of children with a firm but fair approach, believing that education was the key to opportunity on an island beginning to change.
But alongside him, just as steady and just as important, was Ms. Ramona.
For more than 25 years on Hilton Head, and over three decades in the classroom overall, she taught at Bluffton Elementary, Bluffton Graded, and Hilton Head Elementary. Day in and day out, she did the quiet, meaningful work that defines great teachers, shaping young minds, building confidence, and helping children find their footing in a changing world. Where Isaac helped guide the direction of the school, Ramona lived the day-to-day heartbeat of it, one student at a time.
Together, they saw needs others might have overlooked. When children missed school to care for younger siblings while their parents worked, they didn’t ignore it, they worked to solve it. The Children’s Center was born from that understanding, giving working families support and young children a place to begin learning before ever entering a classroom.
Their impact reached far beyond school grounds. Isaac helped lead efforts that supported education, healthcare, and the broader community, while Ramona’s influence continued through every student she taught and every family she touched. Between them, they helped shape not just students, but the character of the island itself.
They were respected not just for what they did, but for how they carried themselves. Fair, steady, and deeply committed. It didn’t matter where you came from, if you were part of this community, you mattered. And if you needed guidance, they were there.
Years later, the community found a way to say thank you. A road was named in their honor near Hilton Head Elementary, a quiet but lasting reminder of the path they helped create for so many others.
Today, it’s easy to look around and see what Hilton Head has become. But beneath the growth and change, there are roots that still hold strong.
Paul Tollefson is the Director of Tennis at the Hampton Hall Club. After moving from Hilton Head to Bluffton he became enthralled with the history of the town and the people and cultures that call it home. He has found a passion in writing and enjoys being able to share the stories and pictures of long-time locals. He is the co-creator of the Facebook page “Bluffton Then and Now.”