Oahu Railway and Land Company Opens First Railroad in Hawaiian Islands

On November 16, 1889, the Oahu Railway and Land Company (OR&L) began operating on Hawai`i's third largest island, Oahu.

The brainchild of Massachusetts native Benjamin Franklin Dillingham, the railroad made it possible to move agricultural products from inland to port, stimulating the local economy and providing a valuable transportation route for decades.

Dillingham arrived in Hawai`i in 1865 as first mate of the sailing ship Whistler. Prevented by a fractured leg from returning to sea, Dillingham made Oahu his home and began investing in its future. Within four years, he was a partner in a local hardware company supplying goods for the growing sugar industry. Dillingham also invested in a dairy business. He was interested in real estate, but failed to raise the money to purchase the land for speculation. In 1888, Dillingham obtained a concession from the Hawai`i legislature to build the OR&L and succeeded in raising the money to build this venture. He scheduled the opening of the short line-railway, which originally ran nine miles, to coincide with the birthday of Hawaiian King Kalakaua.

Early revenues for the OR&L were meager, but as Dillingham had foreseen, the railway's presence stimulated land sales and new agricultural ventures, including pineapple and sugar plantations. By the early 1900s, the expanded 160-mile railway cut across the island, serving several sugar plantations, pineapple farms, and the popular Haleiwa Hotel. As Oahu's pineapple, sugar, and tourism industries grew, profits for Dillingham's railway followed suit.

An additional, and significant, source of revenue for the OR&L came from passenger fares to and from the U.S. Army's Schofield Barracks near the center of the island. From 1909 until the late 1930s, and again during World War II, the OR&L transported troops across Oahu, which had few cars and often shoddy roads. After World War II, the railway's fortunes changed as passenger revenues plummeted and trucks began taking over the agricultural business. The OR&L abandoned service outside Honolulu and its harbor in 1947. In 1972, it closed its remaining service to the Iwilei canneries and docks. The OR&L right-of-way and terminal are on the state and National Register of Historic Places.

The OR&L was conceived and brought to life by Benjamin Dillingham, a self-made businessman who arrived in Honolulu as a sailor in 1865. After falling from his horse and breaking his leg while riding in the countryside, Dillingham was forced to stay in Hawai‘i and recuperate. It was at this time that he decided to make the island kingdom his home. Fortunately Dillingham had a great deal of business acumen and soon became quite wealthy and influential in the early Honolulu community. Among his various development ideas, he conceived in the 1870s of the relatively arid ‘Ewa Plain as an excellent location for human settlement. However, there were two problems: a lack of water and, more significantly, a lack of transportation, for at this time a trip from Honolulu to the ‘Ewa by horse-drawn wagon was an all-day affair. The key was to build a railroad. Around the time Dillingham was dreaming of constructing his railroad, another early and important businessman, James Campbell successfully dug ‘Ewa's first artesian well at Honouliuli in 1879, effectively solving the water problem. Campbell, who had purchased 40,000 acres (162 km²) of ‘Ewa land from the Hawaiian crown thought he might start a cattle ranch, but quickly realized that ‘Ewa's rich volcanic soil (most of which overlay a massive ancient coral reef formation) combined with year-round sunshine and a ready supply of water was ideal for growing sugar cane. Within a couple of years sugar plantations were sprouting up in this southwestern part of O‘ahu. The need for reliable transportation between the harbor at Honolulu and the ‘Ewa was becoming essential.

While Dillingham's dream of large-scale human settlement on the ‘Ewa Plain would have to wait until the last decades of the twentieth century, his plan for a railroad that served the area came together fairly quickly. After leasing Campbell's ‘Ewa and Kahuku land in order to start two sugar plantations Dillingham obtained a government charter for a railroad. It was granted by King David Kalakaua on September 11, 1888, and soon after the OR&L was organized. After securing the necessary capital, Dillingham broke ground in March 1889 with a goal of connecting the twelve miles (19 km) between Honolulu and ‘Aiea (as demanded in the charter) by the fall of 1889. On November 16, 1889, the king's birthday, the OR&L officially opened for traffic, giving free rides to more than 4,000 curious and excited people that day. Over the next ten years the OR&L would see exponential growth. By 1892 the line was 18.5 miles (29.8 km) long, reaching ‘Ewa sugar mill, home of Dillingham's ‘Ewa Plantation Company property. Although progress stalled somewhat during the chaos of the late Kingdom and early Republican periods, by 1895 the railroad had passed through what would become the junction of Waipahu, traversed the ‘Ewa plain, and was skirting the breathtaking Wai‘anae coast to a sugar mill located there. After issuing gold bonds in January 1897 the company was able to extend the railroad around O‘ahu's rugged Ka‘ena Point to Hale‘iwa on the north shore (which it reached in June 1897) where Dillingham built a tourist hotel. By December 1898 the main line was complete, stretching past Waimea Bay and Sunset Beach all the way to Kahuku and the Kahuku sugar mill a little past the island's northernmost tip. Although some early surveys were carried out for a proposed circle-island line, that scheme was never seriously considered. In 1906 an 11-mile (18 km) branch line was constructed from Waipahu up the Waikakalua Gulch to Wahiawa and the pineapple fields of central O‘ahu. The railroad had taken its final shape.

A railroad in Honolulu, financed by Castle & Cooke, becomes the first in Hawaii.