Benjamin Franklin Dillingham

Benjamin Franklin Dillingham fell off a rented horse, and the history of modern Hawai‘i was changed forever. Dillingham was
a New Englander, born on Cape Cod in 1844, and he went to sea at the age of 14. After a series of adventures including capture by a Confederate raider and a rapid rise in rank, he landed in Honolulu as first mate aboard the bark Whistler in 1864. He was 20. After breaking his leg in the topple from the horse, he was carried to the American Marine Hospital in Nu‘uanu to heal. The Whistler sailed without him, and Dillingham was an ex-seafaring man, ashore for good.

After recuperating, he found work at a local hardware store. An entreprenurial spirit bubbled within, and in a few years he had borrowed some money and was the store’s owner. He also married the daughter of a local missionary and started a family. Frank Dillingham’s businesses—the hardware operation and later a large dairy—struggled with heavy obligations for decades, and he was constantly searching for a "big score" that would finally eradicate his debts and provide for his family.

That score was the Oahu Railway & Land Company, a narrow-gauge operation that established sugar as a phenomenally profitable crop on Oahu. The primary line headed west from the main station in downtown Honolulu, eventually stitching together sugar plantations in Aiea, Waipahu, Ewa, Waianae, Waialua, and Kahuku. A later branch wending its way to the center of the Island served the pineapple plantations around Wahiawa. For almost 60 years—from 1889 to 1947—OR&L trundled both freight and passengers around the island, creating great fortunes not only for the Dillinghams, but for many others as well. This book is the story of that line.

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