In 1698, Hilton Head Island was granted as part of a barony to John Bayley of Ballingclough, County of Tipperary, Kingdom of Ireland.
Another John Bayley, son of the first, appointed Alexander Trench as the island's first retail agent.
For a time, Hilton Head was known as Trench's Island.
In 1729, Trench sold some land to John Gascoine which Gascoine named "John's Island" after himself.
The land later came to be known as Jenkin's Island after another owner.

In the mid-1740s, the South Carolina provincial half-galley Beaufort was stationed in a cove at the southern tip of Hilton Head to guard against intrusions by the Spanish of St. Augustine.
The point and cove are named after Captain David Cutler Braddock, commander of the Beaufort.
Captain Braddock was a mariner and privateer of note in Colonial times.
Earlier, he had been placed in command of the Georgia schooner Norfolk by James Oglethorpe, founder of Georgia, and helped chase the Spanish back to St. Augustine after their failed 1742 invasion of St. Simons Island.
After relocating to Savannah in 1746, he served two terms in the Georgia Commons House of Assembly while earning a living as a highly active privateer.
He drew a well-known chart of the Florida Keys while on a privateering venture in 1756.
The chart is in the Library of Congress.

In 1788, a small Episcopal church called the Zion Chapel of Ease was constructed for plantation owners.
The chapel's old cemetery, located near the corner of William Hilton Parkway and Mathews Drive (Folly Field), is all that remains.
Charles Davant, a prominent island planter during the Revolutionary War, is memorialized there.
Davant was shot by Captain Martinangel of Daufuskie Island in 1781.
This location is also home to the oldest intact structure on Hilton Head Island, the Baynard Mausoleum, which was built in 1846.

William Elliott II of Myrtle Bank Plantation grew the first crop of Sea Island Cotton in South Carolina on Hilton Head Island in 1790.

During the Civil War, Fort Walker was a Confederate fort in what is now Port Royal Plantation.
The fort was a station for Confederate troops, and its guns helped protect the 2-mile wide (3 km) entrance to Port Royal Sound, which is fed by two slow-moving and navigable rivers, the Broad River and the Beaufort River.
It was vital to the Sea Island Cotton trade and the southern economy.
On October 29, 1861, the largest fleet ever assembled in North America moved south to seize it.
In the Battle of Port Royal, the fort came under attack by the U.S. Navy, and on November 7, 1861, it fell to over 12,000 Union troops.
The fort was renamed Fort Welles, in honor of Gideon Welles, the Secretary of the Navy.

Hilton Head Island had tremendous significance in the Civil War and became an important base of operations for the Union blockade of the Southern ports, particularly Savannah and Charleston.
The Union also built a military hospital on Hilton Head Island with a 1,200-foot (370 m) frontage and a floor area of 60,000 square feet (6,000 m²).

Hundreds of ex-slaves flocked to Hilton Head Island, where they could buy land, go to school, live in government housing, and serve in what was called the First Regiment of South Carolina Volunteers (although in the beginning, many were "recruited" at the point of a bayonet).
A community called Mitchelville (in honor of General Ormsby M. Mitchel) was constructed on the north end of the island to house them.

The Leamington Lighthouse, also known as the Hilton Head Rear Range Lighthouse, was built in the 1870s on the southern edge of what is now Palmetto Dunes Oceanfront Resort.

On August 27, 1893, the Sea Islands Hurricane made landfall near Savannah, with a storm surge of 16 feet (5 m), and swept north across South Carolina, killing over a thousand and leaving tens of thousands homeless.
In 1698, Hilton Head Island was granted as part of a barony to John Bayley of Ballingclough, County of Tipperary, Kingdom of Ireland. Another John Bayley, son of the first, appointed Alexander Trench as the island's first retail agent. For a time, Hilton Head was known as Trench's Island. In 1729, Trench sold some land to John Gascoine which Gascoine named "John's Island" after himself. The land later came to be known as Jenkin's Island after another owner.
In the mid-1740s, the South Carolina provincial half-galley Beaufort was stationed in a cove at the southern tip of Hilton Head to guard against intrusions by the Spanish of St. Augustine. The point and cove are named after Captain David Cutler Braddock, commander of the Beaufort. Captain Braddock was a mariner and privateer of note in Colonial times. Earlier, he had been placed in command of the Georgia schooner Norfolk by James Oglethorpe, founder of Georgia, and helped chase the Spanish back to St. Augustine after their failed 1742 invasion of St. Simons Island. After relocating to Savannah in 1746, he served two terms in the Georgia Commons House of Assembly while earning a living as a highly active privateer. He drew a well-known chart of the Florida Keys while on a privateering venture in 1756. The chart is in the Library of Congress.
In 1788, a small Episcopal church called the Zion Chapel of Ease was constructed for plantation owners. The chapel's old cemetery, located near the corner of William Hilton Parkway and Mathews Drive (Folly Field), is all that remains. Charles Davant, a prominent island planter during the Revolutionary War, is memorialized there. Davant was shot by Captain Martinangel of Daufuskie Island in 1781. This location is also home to the oldest intact structure on Hilton Head Island, the Baynard Mausoleum, which was built in 1846.
William Elliott II of Myrtle Bank Plantation grew the first crop of Sea Island Cotton in South Carolina on Hilton Head Island in 1790.
During the Civil War, Fort Walker was a Confederate fort in what is now Port Royal Plantation. The fort was a station for Confederate troops, and its guns helped protect the 2-mile wide (3 km) entrance to Port Royal Sound, which is fed by two slow-moving and navigable rivers, the Broad River and the Beaufort River. It was vital to the Sea Island Cotton trade and the southern economy. On October 29, 1861, the largest fleet ever assembled in North America moved south to seize it. In the Battle of Port Royal, the fort came under attack by the U.S. Navy, and on November 7, 1861, it fell to over 12,000 Union troops. The fort was renamed Fort Welles, in honor of Gideon Welles, the Secretary of the Navy.
Hilton Head Island had tremendous significance in the Civil War and became an important base of operations for the Union blockade of the Southern ports, particularly Savannah and Charleston. The Union also built a military hospital on Hilton Head Island with a 1,200-foot (370 m) frontage and a floor area of 60,000 square feet (6,000 m²).
Hundreds of ex-slaves flocked to Hilton Head Island, where they could buy land, go to school, live in government housing, and serve in what was called the First Regiment of South Carolina Volunteers (although in the beginning, many were "recruited" at the point of a bayonet). A community called Mitchelville (in honor of General Ormsby M. Mitchel) was constructed on the north end of the island to house them.
The Leamington Lighthouse, also known as the Hilton Head Rear Range Lighthouse, was built in the 1870s on the southern edge of what is now Palmetto Dunes Oceanfront Resort.
On August 27, 1893, the Sea Islands Hurricane made landfall near Savannah, with a storm surge of 16 feet (5 m), and swept north across South Carolina, killing over a thousand and leaving tens of thousands homeless.
Hilton Head Island, South Carolina