| 1663 | Captain William Hilton sailed from Barbados on "The Adventure and arrived at Port Royal Sound. The island was called Hilton's Head. |
| 1698 | John Bayley of Ireland took title to 16,200 acres. 24 years later he appointed his son, Alexander Trench, to be the first real estate agent. The Island was re-named "Trench's Island." |
| 1733 | Savannah was founded by James Oglethorpe. |
| 1740 | Indigo introduced to the Island. Bricks of dye were sold to the English for dying fabrics. |
| 1778 | "Zion Chapel of Ease" an Episcopal Church was constructed at Mathews Drive and Wm. Hilton Parkway. |
| 1790 | First successful crop of long-staple or Sea Island cotton at Myrtle Bank Plantation, now Dolphin Head in Hilton Head Plantation. |
| 1813 | British forces landed on Hilton Head and burned most of the houses that existed at the time. |
| 1860 | In December, South Carolina was the first state to secede from the Union. |
| 1861 | Fort Walker was built in July at the entrance of Port Royal Sound to protect the area from Union Attacks. |
| 1861 | On November 7th Union forces attacked Fort Walker in the Battle of Port Royal. 13,000 troops flooded onto the island immediately following the battle. |
| 1862 | Post Office and island name was changed to "Port Royal" which was the Union's Department of the South. |
| 1862 | General Ornsby Mitchel set the town of Mitchelville to house the island's contraband community. This was the first Freedman's Village now along today's Beach City Road. |
| 1865 | On February 1st President Lincoln signed the 13th Amendment to end slavery. |
| 1872 | Island's offical name was changed to Hilton Head Island. |
| 1893 | An enormous hurricane and tidal surge hit the island and killed 2,000 people. |
| 1920's | Boll Weevils destroyed almost all of the Sea Island Cotton in the region. Oystering became a primary source of income. The Hudson and Tommer families operated oyster factories from the 1890's to the 1950's. |
| 1940 | Island's population was approximately 1,100, most of who were Freedmen descendants. A great storm hit the island leaving many stranded and many structures damaged. |
| 1949 | Lumber associates from Hinesville, Georgia formed the Hilton Head Company and bought 20,000 acres on Hilton Head's southern end. One was Joseph Fraser. |
| 1950-1952 | Logging took place on 19,000 acres of the island. There were 31 lumber mills and the island's population was only 300 residents. |
| 1950 | Palmetto Electric Cooperative brought the first electricity to the island. |
| 1953 | A state-operated car ferry began running from Buckingham Landing to Jenkins Island, now Outdoor Resorts. The ferry held 4 cars. Price was 10 cents for pedestrians and $1.25 for cars. |
| 1954 | Hilton Head Elementary opened at Wild Horse Road and Hwy. 278. |
| 1955 | Sea Crest Motel opened with two rooms and expanded to eight by 1960. |
| 1955 | Katie McElveen opened the first restaurant Roadside Restaurant on Hwy. 278. Today it is Parkway Medical Center. |
| 1956 | James F. Byrnes Bridge, a two-lane swing bridge, was constructed at a cost of $1.2 million. The cost for a round trip toll was $2.50. 48,000 cars crossed the bridge in 1956. The toll was discontinued in 1959. |
| 1956 | Joseph Fraser withdrew from the Hilton Head Company. His son Charles E. Fraser bought his interest and began developing it into Sea Pines Plantation. |
| 1956 | Norris and Lois Richardson opened the first supermarket on the island at Coligny Circle. |
| 1956 | Hilton Head Island Chamber of Commerce was established. |
| 1958 | First deeds to lots were signed. Beach front lots were sold for $5,350.00. |
| 1958 | The first telephone service was established by Hargray Telephone Company. |
| 1958 | The William Hilton Inn opened on South Forest Beach Drive with 56 rooms. It was torn down in the 1990's to build the Marriott Grand Ocean Resort. |
| 1960 | The island's first golf course, The Ocean Course, was built. |
| 1964 | Bank of Beaufort began offering banking services a few hours a week. |
| 1965 | Sea Pines Medical Center was built. It was staffed by a retired doctor. |
| 1965 | Hilton Head's first rural mail route. |
| 1967 | Hilton Airport opened. |
| 1969 | Harbour Town Village was completed. |
| 1969 | First Heritage Classic Golf Tournament. |
| 1970 | A group of islanders effectively stopped development of a $100 million BASF chemical plant three miles from Hilton Head. |
| 1971 | Island Packet was first published. |
| 1972 | 1st movie theater opened in Coligny Plaza. |
| 1975 | Hilton Head Hospital was completed. |
| 1982 | Four-lane bridge was built to replace the two-lane swing bridge. Island's population was 12,500 residents with more than 500,000 visitors each year. |
| 1983 | Town of Hilton Head Island was incorporated as a municipality. First mayor was Ben Racusin. |
| 1993 | Sun City Construction began for a 5,100 acre development. |
| 1995 | Permanent year-round population exceeded 28,000 people with over 1.5 million visitors. |
| 1996 | Self Family Arts Center opens, now the Arts Center of Coastal Carolina. |
| 1998 | Cross Island Parkway opened in January at a cost of $81 million. |