In 1834, John Paty sailed for the first time to Hawai‘i in the brig Avon, of which he was master and part owner, accompanied by his wife and brother, and arrived at Honolulu in June of that year.  (They had three children while in Hawaiʻi, John Henry Paty (1840,) Mary Francesca Paty (1844) and Emma Theodora Paty (1850.)

In 1860, “Capt John Paty, as a ship master out of Honolulu, and the valuable assistance rendered by him in the furtherance of commercial intercourse between the Hawaiian Islands and adjacent ports in foreign countries, as evidenced by the accomplishment of his one hundredth passage across the Pacific.”   (The Friend, November 1, 1860)

In 1865, Paty, on another run to the Islands, hired Benjamin Franklin (Frank) Dillingham as first mate on the bark Whistler, on the San Francisco/Honolulu run.

Frank, the son of Benjamin Clark Dillingham, a shipmaster, and Lydia Sears (Hows) Dillingham, was born on September 4, 1844 in West Brewster, Massachusetts. Frank left school at 14 and shipped on his uncle’s vessel for a voyage around the Horn to San Francisco. 

“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 would indeed return, and on his third trip aboard the Whistler, he rented a horse. “Sailors are notoriously unfamiliar with horses” he later wrote—describing his collision with a carriage. Ships and sailors were of economic import in the Islands, and on July 29, 1865, the Pacific Commercial Advertiser ran a short piece on his accident:

“The first officer of the bark Whistler Mr Dillingham, whose leg was broken last Friday night by being thrown from a horse, in a collision with a carriage on the vally road, is now at the American Marine Hospital, where he receives every care and attention, and is in a favorable condition for recovery.”

The Whistler could not wait and sailed without him. Ultimately, and unknown to anyone at the time, this changed to course of economic history in the Islands and resulted in lasting legacies.

While recovering, Dillingham had a long time to reflect upon his options. This time he was more serious about staying ashore. Already in love with these Islands, he had met Emma Louise Smith on an earlier visit.

Despite tales of her nursing him back to health, she was away in New England while Frank was recuperating. She was also engaged to another man whom by all accounts she did not love. Dillingham’s patience in slowly courting Emma demonstrated a determination for which he later became known.

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 8^th 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 6^th 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 44^th 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.”

They laughed at him and called it ‘Dillingham’s Folly.’ But Benjamin Franklin Dillingham’s dream of a railroad into the wilderness of West Oahu carried the promise of a sugar industry and major developments that would change Hawaii forever. (Wagner)

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 [OR&L], 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.”

On September 4, 1889, Mr. Dillingham’s forty-fifth birthday, the first train to run out of Honolulu took an excursion party one-half mile into the Palama rice fields.

‘Dillingham’s Folly’ had now become the greatest single factor in the development of O‘ahu and Honolulu.  (Nellist)

“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)

The rail line was extended, reaching Waianae in 1895 and, with Waialua plantation enormously expanded under Mr. Dillingham’s driving leadership, the railroad eventually was extended there and on to Kahuku. (Nellist)

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.”  (Sugar, May 1918) 

On his death in 1918 at age 74, Dillingham was hailed as a “master builder” and Honolulu’s financial district closed its doors out of respect.   (Wagner)  The Islands would have been different, if not for a sailor breaking his leg riding a horse.

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. (Information in this post taken, in part, from ‘Next Stop Honolulu.’)

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