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Some hold that the Whitehall rowing boat design was introduced from England. However the famed nautical historian Howard I. Chappelle, cites the opinion of the late W. P. Stephens that in New York City there is a Whitehall Street and this was where the Whitehall was first built. Chapelle, Stephens and others agree that the design came into existence some time in the 1820’s in New York City, having first been built by navy yard apprentices who had derived their model to some extent from the old naval gig.

Quoting for "Rudder" magazine, August 1943, Captain Charlton L. Smith states a somewhat contrary view, "This delver into nautical lore has never been able to ascertain whether the Whitehall boat originated at Whitehall, New York, or at Whitehall, England. It is extremely likely from the latter place. At any rate the model of a "pure breed" Whitehall that was so useful a rowed-on-the gunnel workboat at Boston and at The Battery at New York City and, later, at San Francisco, evolved from the English Wherry."

Howard Chapelle states in his book "American Small Sailing Craft" that "The Whitehall represents a refinement in an old type rather than a distinct and local innovation. This rowboat is on the same general model that was used in very fast pulling boats, the wherry, cutter, and gig from 1690 or earlier, on to the end of the nineteenth century." All of these rowboats were of course constructed of wood, the only medium used at the time. Chappelle further states that "Originally the Whitehall was lap-strake, but caravel had become common in the New York boats by 1850."

Quoting John Gardner, "The Whitehall was not a ship’s boat, but a vehicle of harbour and coastwise transportation. Intended primarily to be rowed, but capable of a good showing under sail as well, it was fast, seaworthy, and trim. Whitehalls were in great demand in the days of sail on the waterfront of a big commercial port such as was New York City in the early nineteenth century. Not only were these boats the choice of crimps and boarding house runners, but of nearly everyone else as well who required reliable and expeditious transportation about the waterfront from one part of the harbour to another ship chandlers, brokers, newspaper reporters, insurance agents, doctors, pilots, ship’s officers, port officials, and many others."

Whitehalls ranged in size from single rowing station 12 footers to five station boats topping out at 24 feet overall. The small rowboats were used as for-hire craft and the transport of one or two passengers. Larger rowboats of 16 to 18 feet were used by ship’s chandlers to carry samples or to take out gear in an emergency. The largest were used by small groups of thugs called press gangs, who rounded up the often drunk and disorderly ship’s crews and returned then to their vessels.

Colourful stories are associated with the "runners" who under oar and sail ventured out to meet sailing ships as they approached harbour. A salesman’s lot was certainly adventurous in those days as this chap was a highly competitive representative of one of several "deep water boarding houses" actively engaged in lining up clients. Closing with the approaching sailing ship they would swing their Whitehall about and, rowing furiously, approach the larger ship’s bow. Using a long slender pole, a grapple hook and line would be slipped onto the fore lee chains, line payed out to a safe distance, and the Whitehall then warped alongside, where one of the runner’s crew would slip nimbly aboard. A half pint slipped into the right hands assured him of a welcome aboard and an ear or two to ply.

Captain Smith, who was born in Boston in 1869, and who personally witnessed this era tells in the aforementioned "Rudder" article the story of a deep water boarding house owner by the name of Sorenson. "Captain Alfred Sorenson usually got what he went after, whether he was in quest of sailors for his boarding-house or to pluck a fellow being from a watery grave. He outran the fleet of Whitehalls once. He reached a point off the tip of Cape Cod. Came a howling winter gale. Was Alfred fazed? He was not. Rolling, or furling his sail tightly he bent on his warp. With this sea anchor he lay head to it. After thirty-six hours of exposure, he spotted a ship and came home." According to Captain Smith it was because these boats rowed so easily in calms and sailed so well in a breeze that they were even used by the New York Harbour Police.

The Whitehall skiff was the recognized champion in speed and it was only natural that unofficial competition led to organized racing. Many stories are told of the inter-city competition between Boston and New York and the large sums that were wagered on these challenges, Rowing became the principal American competitive sport on the Eastern seaboard from the middle to the end of the nineteenth century and it was the influence of the Whitehall as much as anything else that made it so.

The Whitehall represents an example of a "golden period" of marine design and craftsmanship and its maritime heritage is renewed in Whitehall Reproductions’ replica designs. Growing interest in marine heritage and clean, healthy recreation is causing a rebirth of these traditional craft which are a fusion of the fine workmanship of the past with the best of modern materials available today. They embody the appearance of beauty of a Whitehall and offer the ease of maintenance and the durability of modern materials. These classic reproductions provide the experience of traditional rowing, slide seat rowing or sailing in a legendary classic design that reached it’s pinnacle over a century ago.