Long before the majestic tall ships of the European powers touched upon Maui’s shores...
Ka‘anapali — To people worldwide the name conjures up visions of white sand, rolling surf and tropical nights under the moon. Yet while most visitors think of Ka‘anapali as a premier modern vacation destination, many would be surprised to know that Ka‘anapali has a history that stretches from the '60s all the way back to the days of the ancient Hawaiian people.
This beautiful shorline was the home to a substantial thriving community of native Hawaiian people. Many legends and historical events took place just a stones throw away from the modern shops and restaurants that now line one of Hawaii's longest beaches. One such spot, which is probably the most famous landmark in Ka‘anapali, is Pu‘u Keka‘a (commonly known as Black Rock). The Hawaiian people believed this was a sacred spot where the souls of the deceased would leap from this physical world into the spirit one.
Chief Kahekili, who was one of Maui's most famous chiefs of old, made history among his people at Pu‘u Keka‘a. Kahekili excelled in the game of lele kawa, or cliff diving. Yet the Chief sought to gain respect and loyalty from the many warriors who also excelled at lele kawa. Challenging the spirits who lived in the area, he climbed the large promontory and leaped into the sea below. The other warriors feared the specters of Pu‘u Keka‘a and did not dare follow. Today every evening at sunset, a diver from the Sheraton Maui recreates this leap of bravery by gracefully diving from the top of the rock into the ocean.
Another major event that took place at Ka‘anapali long before the age of contact was the Battle of Koko ‘O Na Moku. Two brothers who vied for the coveted royal crown met on this field where the first hole of the Ka‘anapali North Course is now. The bad blood that ran between these two brothers soon ran on the field as thousands of warriors met in a fierce battle. The combatants would battle the whole day, and then in an act of military honor that is known among those who share the code throughout the world, they retreated to separate camps. Their tenders were allowed to remove the bodies of the fallen and injured. The next day the two sides would meet again to contest the brothers struggles in battle. Koa war canoes crashed through surf that churned red with blood that flowed into the ocean and delivered reinforcements and supplies. Kamehamehanui eventually prevailed, and ruled the area for many years.
The Hawaiian villages at Ka‘anapali eventually disappeared as the plantation era was ushered in. But the emergence of a new age didn't mean that Ka‘anapali's significance had faded. The area north of Black Rock became a camp for the immigrant families brought in to work for the sugar companies. Near Black Rock stands a dilapidated pier that used to be an important hub of shipping operations for the West Side. A train that ran from the mill to the dock offloaded cane and cattle bound for Honolulu and brought in supplies for the workers.
On the south side of Black Rock stood a racetrack whose length ran from The Whaler all the way to the south end of The Westin Maui. Horse racing was a favorite sport of the Hawaiian royalty as well as plantation owners and workers. Many used the opportunity to pad their incomes with bets on the outcome of the races. The track thrived until the end of World War I. During World War II, many of the shipping operations off Ka‘anapali were moved to other areas of the island. For two decades, Ka‘anapali became an almost deserted area that was home to prickly kiawe trees, wetland brush and occasional fishermen.
In the early '60s a company called AMFAC investigated the area and decided this would be a perfect place to build a resort community. Visitors could experience the sun, sand and surf of Maui and play golf, tennis and other leisurely activities. A small airport was built on the north beach area of Ka‘anapali and the wild growth of trees and grass was cleared and turned into two majestic golf courses. The airport was the home to Royal Hawaiian Airlines, a fleet of Cessna 420s that connected West Maui to the other islands. It soon became home to “High School” Harry, a famous bartender who ran the Windsock Lounge, a little bar located up in the top of the airport. The Windsock Lounge was not only famous for Harry and his Bloody Mary, but because all the walls and the ceiling were decorated with thousands of business cards. Cards from all over the world had been left there by travelers passing through. A true sign that even in those days Ka‘anapali was fast becoming a worldclass resort.
Another traveler who became acquainted with Ka‘anapali in the 1960's was so enamored of it, he made it one of the locations for his popular movies that were made in Hawai‘i. The King was filmed at the old airport, the Sheraton Maui and the grounds around Ka‘anapali. The Ka‘anapali Beach Resort was also featured in national TV broadcasts showcasing golf tournaments held there between the 1960's and 1980's. Eager to promote the Ka‘anapali golf experience, AMFAC lobbied to host major PGA and LPGA tournaments on the scenic golf courses at the resort.