There is no evidence that the area was previously settled by a
Native American population. On August 28, 1903, the wooden
steamship Santa Ana, operated by
Pacific Clipper Steamship Company, brought the first permanent settlers to
Seward, Alaska. The cape was named after Captain E.E. Caine, who was a pioneer of commercial marine transportation between the contiguous United States and Alaska and one of the company owners. During
World War II, the strategic importance of Caines Head was recognized early. The cape protrudes deep into
Resurrection Bay, compelling vessels entering the bay to navigate around Caines Head before to reaching the port of Seward. The cape features a steep elevation of , an extremely rugged shoreline, and a difference between high and low tides, effectively obstructing a marine landing. Seward's port was considered critical to wartime logistics, as it was an ice-free port at the south
terminus of
Alaska Railroad. In July 1941, the
US Army deployed 277 men and four 155-mm guns on Caines Head. In July 1942, several months after the Pearl Harbor Attack and a month after the
Imperial Japanese Army's invasion of the
Aleutian Islands, the US Army increased its presence and began constructing permanent fortifications on Caines Head. Over of roads were built for military purposes; however, they were never connected with Seward. Instead, docking facilities were constructed at the north end of the road network. Permanent
artillery batteries were constructed on Caines Head, and a radar installation and submarine loop station were maintained in Resurrection Bay for their support. The installations on Caines Head were
christened Fort McGilvray on March 25, 1943. The defense project was almost completed by February 1944, but successful US Army and Navy advances in the
Pacific Theater of World War II rendered the project irrelevant, and the battery was abandoned on April 7, 1944. Later, the battery was dismantled on March 4, 1947. In 1971, Caines Head area was designated as Caines Head State Recreation Area. The intent was to develop outdoor recreation opportunities and conserve the remains of Fort McGilvray. By 1974, the area was enlarged to , in 1995, an additional were added, thus reaching the present area of . The increase in tourism began in 1984; the first park rangers were appointed to the area in 1985. == Tourism ==