The second-largest barrier island on the East Coast, Hilton Head Island  was inhabited by Native Americans at least 10,000 years ago. The first European to sight the island was Spain’s Francisco Cordillo in 1521, but it didn’t enter mainstream consciousness until the 1663 sighting by Sir William Hilton, who thoughtfully named the island—with its notable headland or “Head”—after himself.
Hilton, who like many of Charleston ’s original settlers was from the British colony of Barbados, was purposely trying to drum up interest in the island as a commercial venture, famously describing his new namesake as having “sweet water” and “clear sweet air.”
Though Hilton Head wasn’t the first foothold of English colonization in Carolina, as Hilton wanted it to be, it did acquire commercial status first as the home of several rice and indigo plantations. Later it gained fame as the first location of the legendary “Sea Island Cotton,” a long-grain variety which, following its introduction in 1790 by William Elliott II of the Myrtle Bank Plantation, would soon be the dominant version of the cash crop.
Hilton Head planters were outspoken in the cause of American independence. The chief pattern in the Lowcountry  during that conflict involved the British raiding Hilton Head and surrounding areas from their stronghold on Daufuskie , burning plantations and capturing slaves to be resold in Caribbean colonies. As a reminder of the savage guerrilla nature of the conflict in the South, British hit-and-run raids on Hilton Head continued for weeks after Cornwallis surrendered.
Nearby [node"78864 link Bluffton] was settled by planters from Hilton Head Island and the surrounding area in the early 1800s as a summer retreat. Though Charleston  likes to claim the label today, Bluffton was actually the genuine “cradle of secession.” Indeed, locals still joke that the town motto is “Divided We Stand.”
Fort Walker, a Confederate installation on the site of the modern Port Royal Plantation development on Hilton Head, was the target of the largest fleet ever assembled in North America at the time, when a massive Union force sailed into Port Royal Sound in October 1861. A month later, the Fort—and effectively the entire area—had fallen, though by that time most white residents had long since fled.
During the Civil War, Bluffton was also evacuated and, like Hilton Head, escaped serious action. However, in June 1863, Union troops destroyed most of the town of Bluffton except for about a dozen homes and two churches.
Though it seems unlikely given the island’s modern demographics, Hilton Head  was almost entirely African American through much of the 20th century. Given its role as a plantation site, the population was always mostly African American, becoming even more so when Union troops occupied the island at the outbreak of the Civil War. Freed and escaped slaves flocked to the island, and most of the dwindling number of African Americans on the island today are descendants of this original Gullah  population.
For the first half of the 20th century, logging was Hilton Head’s main commercial pursuit. Things didn’t take their modern shape until the 1950s, when the Fraser family bought 19,000 of the island’s 25,000 acres with the intent to continue forestry on them. But in 1956—not at all coincidentally the same year the first bridge to the island was built—Charles Fraser convinced his father to sell him the southern tip of Hilton Head Island. Fraser’s brainchild and decades-long labor of love—some said his obsession—Sea Pines Plantation was the prototype of the golf-oriented resort community so common today on both U.S. coasts.
Though Fraser himself was killed in a boating accident in 2002, he survived to see Sea Pines encompass much of Hilton Head’s economic activity, including Harbour Town , and to see the Town of Hilton Head incorporated in 1983. Fraser is buried under the famous Liberty Oak in Harbour Town, which he personally made sure wasn’t harmed during the development of the area.