at the turn of the 20th century. Though not the first railroad on the Big Island, it was certainly the most ambitious. Its principal backer was Benjamin Dillingham, the businessman who also started the OR&L, among numerous other Hawaiian companies. In the late 1890s Dillingham purchased land near the growing city of Hilo, and it was this land that would become his Olaa Sugar Company plantation. On March 28, 1899, Dillingham received a charter to build the original eight miles of the Hilo Railroad that connected the Olaa sugar mill to Waiākea, soon to become the location of Hilo's deepwater port.