For centuries Waikiki was the site of a thriving population known for its freshwater springs, fishponds, Taro (Kalo) fields and traditional thatched roof houses. Blessed with its equable less-rainy climate and with plenty of water flowing from the nearby mountains, it supported a large population that lived in harmony with its productive land and fish resources. Waikiki was first settled some time before 600-800 AD and its beaches provided perfect places for canoes to venture to other parts of Oahu and the other islands. And everybody, including women and children, surfed. In the 1850’s Waikiki was still a quiet resort-like place whereas Honolulu was a small bustling port area with hundreds of trading ships arriving each year and a growing population of foreigners. Waikiki remained a favorite of local royal inhabitants until after Hawaii was annexed by the US in 1893. The construction of the Ala Wai Canal in the late 1920’s drained the wetland areas of Waikiki and this led to its inexorable rise as one of the world’s most sought-after tropical oceanside destinations.
The Waikiki Historic Trail was originally conceived by Hawaiian cultural expert and historian George Kanahele. He was born in 1930 and educated at Kamehameha Schools, Brigham Young University, and Cornell University. In 1994 he wrote a paper called "Restoring Hawaiianness to Waikiki" that proposed 140 ideas for improving Waikiki in ways that both the locals and tourists could appreciate. One of the proposals in that paper was creating the Waikiki Historic Trail.