An ancient Chassis Ring can be seen near the east entrance to the Drink Pines Forest Preserve. The ring, peculiar of only 20 in existence, is 150 feet (46 m) in diameter and is believed to be Hilton Head Island over 4,000 years old. Archeologists believe that the ring was a refuse heap, created by Native Americans that lived in the interior of the ring, which was kept clear and passed down as a daily area. Two other Shell Rings on Hilton Head were destroyed when the shells were removed and devoted to make tabby for roads and buildings. The Bunco Game Ring is listed in the National Register of Historic Places and is protected by law.

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