Named "La Florida" by the Spaniards in 1526, Hilton Head Island was explored and Indian settlements and evidence of agricluture were found throughout. A French Huguenot, named Captain Jean Ribaut, headed an exploration in the area in 1562 and built a fort named Port Royall near the present town of Port Royal in Beaufort County. In 1566, Spanish was a more prominant culture on the island and established a fort on Paris Island, in what is now Beaufort County, called Santa Elena. The demanding European royalty, eager to discover, Queen Elizabeth I sent Sir Francis Drake to drive the Spanish from the land. Development did not begin until 1663, when King Charles II granted the coastal area to 8 Lord Proprietors. They named their territory Carolina.

 In August of 1663, while exploring the Port Royal Sound, English Captain William Hilton sighted the high bluffs of the island, referred to as healdlands. He then named the island after himself, "Hilton Head". In 1717, Colonel John Barnwell was granted 1000 acres on the northwest corner of Hilton Head Island by the Lord Proprietors and became the first white settler. By 1766, 25 other families lived on Hilton Head Island.

Just one mile south of the island, Daufuskie Island, was occupied by the Tories during the Revolutionary War. The British would often raid Hilton Head, burning down plantations and capturing slaves who were later sold in the West Indies. After the war, the island flourished with new vegetation, cotton, rice and other crops, making a healthy recovery.

Hilton Head Island thrives with Civil War history. With South Carolina being the first state to secede from the union, the island became a very important target for union solidiers, as several millionaires lived there. On November 7th, 1861, Union soldiers fired at all settlements while circling around Port Royal Sound. By Noon, Confederate soldiers had lost the battle and 1,000 slaves were freed. Eventually, Union forces reached into the 50,000, and the island was used for stopping many import and export locations all along the lower East Coast. Many slaves retreated to Hilton Head Island because they were safe here. They began building houses, schools and churches.

Eventually, after the war, the island was left to the remaining freed slaves to live and flourish. Their communities consisted of farmers, fisherman, basket weavers and fishnet makers. "Gullah" a blend of slave, native, cadence and Elizabethian English was spoken here. This rich culture survives to this day. As interest in the history of African-Americans on Hilton Head Island grows, more evidence of their lifestyle is being preserved. The Gullah culture continues as community leaders encourage its preservation.

By 1890, Northerners flocked to the island again to hunt and fish. 1000 acres were sold to the North Carolina Hunt Club. Money was scarce and Islanders began bartering with the Northerners for goods and services. By 1931, the African-American population was around 300 and the only access to the island was by water only.

The 1950's brought electricity and telephones to Hilton Head Island. Soon dirt roads became paved roads and bridges were built to replace Ferry boats for easier access. Rapid growth began in the 1970's and population grew from 2,500 to 39,000+. The Island Packet, the first and current daily newspaper, first edition came out in 1970. In 1983, the Town of Hilton Head became Incorporated. Today, Hilton Head Island offers emmense amounts of history and leisure. Championship golf courses, abundant shopping, historical sites and multiple activties make Hilton Head Island the fun, family atmosphere it is today.