Hilton Head First Families – The Simmons


No one wants to be forgotten. Some believe that being remembered is not simply a way to respect those who came before you; it is also a way to keep those people alive for future generations. And when our lives are ones we can be proud of, it becomes our legacy, our priceless gift to those who come after us.

Most of us live simple, ordinary lives that touch our immediate family and friends, and this simplicity is our legacy. But there are some who live expansive lives and leave bigger footprints. These are the rare people who are destined to have a significant impact beyond their immediate family and friends. These are the rare people who stand up to life’s challenges and transform their own circumstances, as well as their own communities, in immeasurable ways, and for this they deserve our respect and recognition. These are the rare people who leave impressive legacies that show a life well-lived has generational impact and historical significance. Charlie Simmons Sr. was one of those rare people, and this is the legacy he has left for the proud Simmons family, and the Hilton Head community.

The Simmons2When you drive down Hilton Head Island’s Spanish Wells Road, you are sure to go over the bridge that was named after Charlie, also known as “Mr. Transportation.” The story of how he used his boat to connect native islanders to the mainland is a well-known one. He established a ferry business that enabled native islanders to bring their crops to the markets in Savannah. Not only did his transportation business impact the lives of the individual islanders, it was also instrumental in increasing the economic strength and overall development of the island. This makes his life and work an important part of Hilton Head’s history.

Charlie had an incredible life and was guided by his vision for Hilton Head. Palmer Simmons, his grandson, admired his grandfather’s foresight and boldness. Charlie saw the need to connect the island to the mainland, and he established a system of boats and trucks that created a “lifeline” to Savannah so that local islanders could sell their goods. This had a significant impact on the development of Hilton Head, allowing it to not only sustain itself, but to also expand. However, according to Dr. Emory Campbell, Charlie Simmons established more than a lifeline to Savannah and the mainland; he established “a lifeline between us and the rest of the world.”

Over the years, Charlie was responsible for bringing countless numbers of people back and forth to the island, including developer Charles Fraser, who established Sea Pines. “Mr. Transportation” also ferried construction materials to Sea Pines, and according to native islander Mary Young, “he also transported the food and the workers to the hotels” as well.

Charles Simmons SrHowever, transportation was not the only focus of his business. Charlie and his family had an impact on local education as well, because he also transported island children by boat to and from the historic Penn Center for schooling, and his first wife, Estalla, “drove the first school bus on the island,” Young says.  

But Charlie didn’t earn the name “Mr. Transportation” simply because of his ferry business. He also transported people on dry land, enabling them to move around more efficiently, transact their business, and communicate with each other more easily.

“Mr. Charlie was very important to the island. He did everything on the island,” Young says. “He was always an upright and hardworking man; when he wasn’t on his boat, he was out plowing his fields. He also had one of the first stores on the island. If he didn’t have what you were looking for, he made sure that he found it for you. On Sunday, he would take us to church in his truck from Spanish Wells to Mitchelville.”  

Even though Charlie’s name is forever linked to transportation, his value to his community was felt in many other ways that are not easy to measure. For example, he was a role model who inspired and awed those around him without knowing it.

“My first memory of Charlie Sr. goes back to when I was 6 or 7 years old and went on my first trip off of the island,” Campbell says, remembering Charlie’s influence on the island and its inhabitants. “His car picked my mother and I up from the house and we drove down some long wooded roads until we got to the boat. Once we got on board, I remember that that boat was loaded with people and their goods on their way to Savannah. During the trip, we stopped at Daufuskie (Island) to pick up more people. The trip took four hours and we ate a meal that was prepared in the kitchen that was on board. What I remember most was the roar of the engine as we sailed to Savannah. Even today, every time I fly, the sound of the plane’s engines brings me back to my first boat ride with Charlie.”  

Stories like this and countless others show the power and depth of Charlie Simmons’ impact on his community. Generations of people were touched by his life and his story. His contribution to Hilton Head will forever stand among the great accomplishments of the island’s residents, because of the obvious role he played in bringing people together. But perhaps the most significant part of his life and legacy is the trail of kindness and generosity that he left behind. Charlie’s grandson, Palmer, captured this when he said, “My grandfather sometimes bartered his services. He wasn’t running the ferry for the money; he did what he did because he loved being on the water and being of service to the island. He was given a variety of things in lieu of payment, from crops to livestock, even land. People always speak very highly of him for all of the good that he did to help them. Until his death, he was just our grandfather. When people would tell us stories of what he had done, we didn’t realize until we got older how much he did and how important his work was.”

One of the greatest legacies that Charlie left his family is his lifelong love of the water. This passion lives on in his grandchildren, for whom boating and fishing are a way of life.

Charles Simmons3

“Water is in our blood. It’s our way of life here,” said great-great-grandson Jermaine Robinson.

Charlie has a historical marker and a bridge named in his honor. Both are enduring symbols that represent a man and his life. But these symbols do not capture the essence of Charlie Simmons and how he changed Hilton Head and the lives of the people in his community. He was a gifted businessman, community servant and a visionary, all part of his enduring legacy. He was brilliant, and devoted himself to the island and its people, and his name and the honor due him will live on for generations to come.

Charlie Simmons Sr. was and is a role model, and his is a living legacy that continues to guide the Simmons family today. Now that’s a legacy.