The origins of Whitehead go back to the Plantation of Ulster when the locality was know as Kinbane (White Head) Like Kinbane on the north coast, the name is descriptive of the limestone headland which was the dominant feature.  In contrast at the far end of the village is the dark basalt headland of Black Head.

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The ruins of Castle Chichester are still visible in the town, the remaining tower was built earlier than 1610, when its association with the Chichester family began. The family were influential in the development of Carrickfergus and Belfast, Sir Arthur Chichester succeeded his brother to become Governor of Carrickfergus after he was killed by the MacDonnells. Arthur Chichester went on to become the Lord Deputy of Ireland.

A small collection of houses and harbour developed around the castle which was known as Castlechichester or Chichester. The area had two other clachans (groups of cottages) Kinbane and Knocknagullagh, over the centuries they merged into one.  At one time a packet ship crossed between Chichester and Scotland with mail and goods, the mail was then dispatched by smaller vessels to Belfast.

The limestone cliffs that surrounded the location were extensively quarried during the 1800s producing stone needed for the developing railway line from Belfast and for export from the natural tidal harbour. The harbour was later developed with a pier to facilitate non tidal shipment. The export of limestone continued to the end of the 1800s century, the quarry eventually closing in 1920.

Major developments came to the village when the Carrickfergus to Larne railway line opened in 1863, the railway company had plans to turn this Edwardian village into a holiday resort. Chichester by the Sea, as it was known, received big incentives from the railway company for anyone who built a villa close to the station. The plan succeeded in turning the village into a unique Victorian seaside resort with many attractions for visitors including a golf club, yacht club, bandstand and promenade with tea rooms.

The village had two railway lines, a  through line to Larne for passengers using the steamers to and from Scotland and an excursion line into the village. the excursion line and platform was opened in 1907 with a  terminus and engine sheds, a maintenance facilities was built later.