First Families of Hilton Head: The Singletons

Photo From left: Christina Bates, Paulette Singleton, Dorothy Singleton, Vernie Singleton and Alvin Singleton

Hilton Head Island has the unique distinction of being the home of Mitchelville, the first black self-governing town in the United States. Stories of what happened in Mitchelville and the continued impact that it had on the Gullah community, the outcome of the Civil War, race relations and even compulsory education today are still unfolding. But little is known about the individuals and families, who after being thrust into servitude in a new land, chose to not only embrace their new surroundings, but to love, nourish and cultivate this island as their home.

Monthly’s series “First Families of Hilton Head Island” will bring attention to the families that made Hilton Head what it is today: a breathtakingly beautiful space that invites relaxation and civility. The effects of Hilton Head can influence you before you even step foot on its soil. From the foot of the bridge to the island, you are graced with a sudden calming visual image of the expanse of the Pinckney Island marshlands. As you cross the bridge, Hilton Head begins to change you. Residents and visitors alike see it as a special place, which is by no means an accident; over time, like many places around the world, the island could easily have been neglected and destroyed, pillaged and abused, and left to be just another place. Gratefully, that is not the case. Hilton Head’s natural beauty remains intact almost as it was in the early 1700s. Of course, it has been altered. Time, technology and development have taken care of that. However, somewhere along the way, someone had to have understood the necessity of protecting this island. The Gullah community has done just that. Because they lived on an island that for years did not have a bridge to the mainland, the Gullah were essentially separated from the rest of the Lowcountry, working with what they had, creating lives for themselves that were made up of hard work as farmers and fisherman, yet full of love and support for each other as a community. The old saying that “it takes a village” was obvious here. Hilton Head was a village where neighbor helped neighbor, where responsibility for each other’s welfare was just “how it was done.”

The first family to be highlighted by the series will be the Singleton family. If you pay attention to the street signs on William Hilton Parkway, Singleton Beach Road is located in the island’s “arch.” The Singleton family’s origin on the island began with slavery. The patriarch, Namen Singleton, was only 12 years old when slavery was abolished, yet he purchased his first property over in the area of Diannah Drive, which is named after his wife. His great-great-grandchildren still live there today.

On the land, he grew cotton as well as pecans and other crops. Through hard work and an entrepreneurial spirit, he was able to buy his second property along the waterfront in the Chaplin area of the island, which is where Singleton Beach is located today. Eventually, between Namen Singleton and one of his sons, Ezekiel, bought over two hundred acres between the Marshland Road area and the waterfront property, which extended as far as Collier Beach, which was passed down to his children.  Ezekiel, who was filled with an entrepreneurial spirit, along with his wife, Rosa May, was able to envision the great potential that the land possessed. Having the forethought of its value as well as location, they developed the beach front property, and built pavilions as well as the Sand Dunes store, drawing Black people from as far away as Atlanta, Charleston and Savannah to the waterfront for entertainment and relaxation. As property owners, the Singleton’s provided an economic boost to their neighbors by renting out some of their land as residential space to those looking for a place to live and work. Over time, the land became a significant source of economic growth for the native islanders. As the Singleton family flourished, they became a model for other natives who were interested in establishing businesses of their own.  

As a result of the central location of the Singletons’ property, the land became prime real estate and boosted the island’s economy while giving the native islanders needed access to a variety of goods and services. This land became a business mecca. The Singletons opened a gas station, and other native islander-owned businesses followed: Bill and Dorothy Dreisson opened Dreisson’s Tailor Shop, Henry Ford practiced his skill as a cobbler, and Nathanial Simmons ran his auto shop. This was a place where friendly neighborhood service was a common part of everyday living.

These days, when we think of major developers, we think of the corporations that developed massive communities like Sea Pines, Hilton Head Plantation and Indigo Run, but the Singleton family deserves credit as a major developer as well. Not only did the Singletons play a significant role in shaping island history and “pulled themselves up by their bootstraps,” they created opportunities for the economic growth and prosperity of their neighbors. The Singletons are among the first to have the vision to see Hilton Head’s potential. The island has changed and many of those businesses no longer exist, but it is impossible to un-write history, and the impact of the Singleton family cannot be undone. What has been left behind, though, are savored memories and Hilton Head’s small-town charm coupled with gracious Southern hospitality, which continues to live on.