Benjamin Franklin (Frank) Dillingham was the son of Benjamin Clark Dillingham, a shipmaster, and Lydia Sears (Hows) Dillingham, born on September 4, 1844 in West Brewster, Massachusetts.
He left school at 14 and shipped on his uncle’s vessel for a voyage around the Horn to San Francisco. During the Civil War, on June 6, 1863, he was nineteen-year-old third mate on the clipper ship Southern Cross bound for New York with a cargo of ‘log wood.’
‘Florida’ was flying the British ensign, though as she steamed closer, she ran up the rebels’ ‘stars and bars.’ A squad of armed Confederate sailors boarded and took Dillingham and the rest of the clipper’s small crew prisoner.
Then, as the new prisoners watched from the deck of their captor, the Southern Cross was set ablaze and sunk. Eventually they were put ashore at Rio de Janeiro and worked their way back to the war-torn United States.
Dillingham headed west, determined to take up residence in San Francisco and find work ashore. An unsuccessful hunt for employment led him back to the sea, and in 1865 he was hired by Captain John Paty as first mate on the bark Whistler, on the San Francisco/Honolulu run.
“A brief sojourn in the city enabled me to realize that I had no training in any other vocation, save that of the sea, and learning that Capt. Paty of the bark Whistler plying between the coast and Honolulu was in need of officers, I applied and obtained the position of first mate without delay.” (Dillingham; Chiddix & Simpson))
Dillingham wrote that he felt at home the first time he came ashore in Honolulu: “After my tempstuous experiences in rounding Cape Horn and the Cape of Good Hope, the trip seemed to me like a pleasure excursion.”
“It felt as if I had anchored in a home port; the cordiality I experienced from all those whom I met removed at once the feeling of being in a foreign land though the streets were filled with several nationalities. The luxuriant foliage, the balmy breezes, the tropical fruits, all afforded such delights that I felt sure I should return.”
He did return, and ultimately stayed after an unfortunate encounter between his horse and a carriage; “The first officer of the bark Whistler, Mr. Dillingham, whose leg was broken last Friday night, by being thrown from a horse, in collision with a carriage, on the valley road …”
“(Dillingham) is now at the American Marine Hospital, where he receives every care and attention, and is in favorable condition for recover.” (Pacific Commercial Advertiser, July 29, 1865) Unfortunately for him, the Whistler left him in Honolulu and sailed away.
He accepted a job as a clerk in a hardware store called H. Dimond & Son for $40 per month. The store was owned by Henry Dimond, formerly a bookbinder in the 7th Missionary Company. In 1850 Dimond had been released from his duties at the Mission and had gone into business with his son.
Dillingham later bought the company with partner Alfred Castle (son of Samuel Northrup Castle, who was in the 8th Company of missionaries and ran the Mission business office;) they called the company Dillingham & Co (it was later known as Pacific Hardware, Co.)
On April 26, 1869, Dillingham married Emma Smith, daughter of 6th Company missionaries Reverend Lowell and Abigail Smith.
But hard times came on Dillingham with the collapse of whaling and the rise of sugar. Large suppliers pulled Dillingham’s credit lines, and his accounts were paid late. Then Dillingham was given the opportunity to buy the James Campbell lands in Ewa.
While he couldn’t raise the money to buy it, Campbell leased the land for 50-years. Dillingham realized that to be successful, he needed reliable transportation.
On September 4, 1888, Frank Dillingham’s 44th birthday, the legislature gave Dillingham an exclusive franchise “for construction and operation on the Island of O‘ahu a steam railroad … for the carriage of passengers and freight.”
Dillingham formed O‘ahu Railway and Land Company (OR&L,) a narrow gauge rail, whose economic being was founded on the belief that O‘ahu would soon host a major sugar industry.
“Among the most important works now in process of rapid construction, is the Oahu railway to Pearl Harbor, which is already approaching completion, so far as grading is concerned. Eleven miles of this line will have the grading completed in two weeks; and of this length ten miles are already finished.”
“The depot itself will be of imposing size and made as ornamental in appearance as convenience and traffic requirements will allow. … The progress of this important work has been so rapid during the month of July that we give it first place among the works in progress during the past month.” (Pacific Commercial Advertiser, July 27, 1889)
“Mr BF Dillingham, promoter of the Oahu Railway and Land Company, on his birthday a year previous, was accosted by an acquaintance with the remark: ‘Well, Mr. Dillingham, you have got your franchise: when are you going to give us the railway?’”
“Mr. Dillingham replied that on his next birthday, that day one year, he hoped to treat his friends to a railway ride. … with a strong company now at his back, the originator of the enterprise, having taken the contract to build the road, resolutely pushed operations to their present advanced stage.”
“When the appointed day arrived Mr Dillingham was ready to celebrate. His engine had been set up some days. Two third class cars, the best passenger accommodation as yet on the ground, were put together. … With a shrill blast from the whistle and the bell clanging, the engine moved easily off with its load. Three rousing cheers were given by the passengers, and crowds assembled at the starting point responded.” (Daily Bulletin, September 5, 1889)
Ultimately OR&L sublet land, partnered on several sugar operations and/or hauled cane from Ewa Plantation Company, Honolulu Sugar Company in ‘Aiea, O‘ahu Sugar in Waipahu, Waianae Sugar Company, Waialua Agriculture Company and Kahuku Plantation Company, as well as pineapples for Dole.
By the early-1900s, the expanded railway cut across the island, serving several sugar and pineapple plantations, and the popular Haleʻiwa Hotel. They even included a “Kodak Camera Train” (associated with the Hula Show) for Sunday trips to Hale‘iwa for picture-taking.
When the hotel opened on August 5, 1899, guests were conveyed from the railway terminal over the Anahulu stream to fourteen luxurious suites, each had a bath with hot-and-cold running water.
Thrum’s ‘Hawaiian Annual’ (1900,) noted, “In providing so tempting an inn as an adjunct and special attraction for travel by the Oahu Railway – also of his (Dillingham’s) creation – the old maxim of ‘what is worth doing is worth doing well’ has been well observed, everything About the hotel is first class…”
The weekend getaway from Honolulu to the Haleʻiwa Hotel became hugely popular with the city affluent who enjoyed a retreat in ‘the country.’
In addition, OR&L (using another of its “land” components,) got into land development. It developed Hawai‘i’s first planned suburban development and held a contest, through the newspaper, to name this new city. The winner selected was “Pearl City” (the public also named the main street, Lehua.)
The railway owned 2,200-acres in fee simple in the peninsula. First they laid-out and constructed the improvements, then invited the public on a free ride to see the new residential community. The marketing went so well; ultimately, lots were auctioned off to the highest bidder.
“Mr. Dillingham, besides creating the O‘ahu Railway, a line for which he struggled twenty-seven years against a public prejudice that would not see its financial possibilities, established Olaʻa plantation on the Island of Hawai‘i and McBryde plantation on Kauai.”
“He retained active management of the Oahu Railway & Land Company until 1915, when he relinquished it to George P. Denison.” (Sugar, May 1918) Dillingham died April 7, 1918 (aged 73.) (Information in this post taken, in part, from ‘Next Stop Honolulu.’)
The Dillingham Transportation Building was built in 1929 for Walter F Dillingham of Honolulu, Hawaiʻi, who founded the Hawaiian Dredging Company (later Dillingham Construction) and ran the Oahu Railway and Land Company founded by his father, Benjamin Franklin Dillingham.
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