In DesBrisay’s words...

Among the islands, none is more widely known than Oak Island, four miles from Chester, so called from the beautiful Oak trees, some of which remain.

It has become famous for the searches from time to time made for treasure supposed to have been buried by the noted pirate, Captain Kidd. The first settlers were John McMullen, and Daniel Mclnnis, father of Mrs. Thomas Whitford, of Chester.

The pits hereinafter referred to were dug on the farm formerly owned by John Smith, who was born in Boston, Mass., August 20th, 1775, and died on the island, after a residence there of seventy-one years, on the 29th of September, 1857. He brought up his children very respectably. His daughter Mary lived in the family to which the writer belongs for sixteen years, and he takes pleasure in here mentioning her name, remembering with gratitude her faithful attention in the days of his childhood, at Chester, and afterwards at Dartmouth.

Several accounts have been given to the writer of work from time to time done on the island, and some of it he has himself witnessed. The leading facts are embodied in the following condensed statement from lengthy papers published December 20th, 1863, and subsequently, by a member of the "Oak Island Association," who said that more than a century before, an old man died in what was then known as the British Colony of New England, who on his death-bed confessed to having been one of the crew of the famous Captain Kidd, and assured those who attended him in his last moments that he had many years previously assisted that noted pirate and his followers in burying over two millions of money beneath the soil of a secluded island east of Boston. This news having been widely spread, many searches were made, but all in vain.

Three men — Smith, Mclnnis (grandfather of James Mclnnis) and Vaughan emigrated from New England to Chester. Smith, and Mclnnis took up land on Oak Island, and Vaughan settled on the adjacent mainland. Mclnnis one day discovered a spot that gave evidence of having been visited by someone a good many years earlier. There had been cuttings away of the forest, and oak stumps were visible. One of the original oaks was standing, with a large forked branch extending over the old clearing. To the forked part of this branch by means of a treenail connecting the fork in a small triangle, was attached an old tackle block. Mclnnis made known his find to his neighbors. Next day the three visited the place, and on taking the block from the tree it fell to the ground and went to pieces.

They found the remains of a road from the tree to the western shore of the island, and they concluded that if Kidd had buried money it was probably here. The ground over which the block had been had settled and formed a hollow. They cleared away the young trees, and removed the surface soil for about two feet, when they struck a tier of flagstones, which they found differed from the island stones, and concluded they had been brought from the vicinity of Gold River. On removing these, they saw they were entering an old pit that had been filled up. The mouth was seven feet in diameter, and the sides were of tough, hard clay; but the earth which had been used in filling was loose, and easy to be removed. Ten feet lower was a tier of oak logs, tightly attached to the sides, and the earth below them had settled nearly two feet. The logs were very much decayed on the outside. Removing these, they went fifteen feet farther down. To get below this they required help, but none seemed willing to assist.

About fifteen years afterwards, Simeon Lynds, of Onslow, visited Chester, and saw Vaughan, to whom his father was related, and the next day they went to the place, and, as a result, he and many of his friends, with tools and provisions, came to the island, and were joined by Smith, Mclnnis and Vaughan. The pit was found to have caved in, and mud had settled at the bottom. On taking this away they came to the three sticks which had been put in the mud by the three first men on leaving off work. They went on, and struck a second tier of logs like those first found. Ten feet lower they came to charcoal, ten feet below it to putty, and farther down to a flagstone about two feet long and one foot wide, with rudely cut letters and figures which they could not decipher. The engraved side was downwards.

On reaching a depth of ninety feet, the earth in the centre became softened, and water began to show itself. At ninety three feet, it increased, and they took out one tub of water to two of earth. Night coming on, they, as usual, probed the bottom with a crowbar, to see if they could strike anything. At the depth of ninety-eight feet, five feet below where the bar entered, they met a hard impenetrable substance, bound by the sides of the pit. They expected the mystery to be solved in the morning, but on returning, they found sixty feet of water, and their bailing buckets failed to lessen the depth. They discontinued the work, and sent a committee to Mr. Mosher, of Newport, considered the best man for such purpose in the Province, to provide a way for removing the water. He prepared a pump, at a cost of £80, and it was lowered to the depth of ninety feet, but before the water reached the surface it burst. Robert Archibald, Esq., uncle to the late Master of the Rolls, then had charge. In the following spring, a new shaft was sunk to the depth of 110 feet, and water then came in until it was sixty-five deep.

In 1848, work was resumed, the old pit was reopened, and twelve days afterwards, the men were down eighty-six feet. On a certain Saturday evening, everything was so far satisfactory, but on returning from morning service at Chester, on the following day, there was sixty feet of water in the pit, and level with that in the bay. A great deal of additional work was done. The water rose in a new pit to the same height as that in the old one.

In 1861, a new shaft was made; but the men were driven out by the coming in of water and mud. In 1863, further work was performed; but it was found impossible to keep out the water.

The work was afterwards carried on by Halifax members of the company, under special agreement with the Association. A new shaft was sunk, and there was confidence in ultimate success; but no discovery of treasure was made.

The writer above referred to stated that he was for fifteen years a member of the "Oak Island Association," occasionally actively engaged at the works on the island, and thus gained information which enabled him to write with confidence on the subject. From all he saw, with what he believed in the experience of others, he had no doubt that the "money pit," and the drains on the island, were purely works of art, constructed at a very early period in the history of the country ; but for what purpose he could not say, and as to whether Kidd's buried treasure lies at the bottom of the "money pit," or whether, as more believe, it does not, he did not feel it safe to offer an opinion.

Sixty men and thirty horses have been at one time engaged on Oak Island. Many years ago, a day was named when all who should visit the island would see Kidd's treasure brought to the surface. Schooner and boat loads of people gathered from all directions. An old German, looking at the work, said, "the deeper they dig, the deeper it sinks."

Parties from abroad have continued the search at intervals, and as recently as 1892 and 1893 new pits were dug. Those who were employed in one of them were told that the ground would cave in, but they were not inclined to believe it. They soon had an indication of the truth, and had been out only about five minutes, when several cartloads fell in. This ended the attempt then made, and the party left the island. Another pit was afterwards dug, but not to any great depth. These latter workings, with others, are said to have been prompted by the dreams of a man in an eastern county, to whom certain spirits appeared, by whom he was taken to the island, and shown the long coveted deposits of gold and silver.

Some of the most advanced counties in the Province have furnished many of the stockholders in the companies from time to time formed to prosecute the search, and notwithstanding the repeated failures, men of much intelligence express their belief that success will yet be achieved.

Henry S. Poole, Esq., who in 1861 was visiting different localities on behalf of the Government, wrote in his report: "I crossed to Oak Island and observed slate all the way along the main shore, but I could not see any rock in situ on the island. I went to the spot where people have been engaged for so many years searching for the supposed hidden treasure of Captain Kidd. I found the original shaft had caved in, and two others had been sunk alongside. One was open and said to be 120 feet deep, and in all that depth no rock had been struck. The excavated matter alongside was composed of sand and boulder rocks, and though the pit was some two hundred yards from the shore, the water in the shaft (which I measured to be within thirty-eight feet of the top) rose and fell with the tide, showing a free communication between the sea and the shaft."

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