The story starts in 1795. In the summer of that year sixteen-year-old Daniel McGinnis, a resident of Chester, the small toen on the eastern shore of Mahone Bay, went canoeing. He paddled four miles across the bay, landing on a small island close to the western shore. It carried a dense growth of oak trees, unlike the other 360-odd islands in the bay. Why that particular island attracted McGinnis is unknown. He pulled up his boat in a crescent-shaped cove on its south-eastern shore. Either then or later he noticed a large boulder, sem-submerged, in which was affixed a heavy ring-bolt. McGinnis roamed through the trees, following an ancient path up the slope from the beach. The trees thinned out and he found himself walking through a wide clearing in the centre of which stood a gnarled and ancient oak tree. Inspecting the tree, McGinnis saw that, some sixteen ft. or so above ground, a branch had been lopped short. It overhung a depression in the ground. (According to one version of the story, and ancient ship's tackle-block hung from the branch, and its bark was scored by ropes.) In the clearing the first growth of wood had been cut down and another was springing up to take its place. Some old stumps of oak trees were visible. McGinnis also noticed the remains of a tolerably well made road running from north-east to south-west on the island.
His curiosity excited and his thoughts boiling, McGinnis hurried home. He returned to the island the next day accompanied by his two friends, John Smith aged twenty, and Anthony Vaughan aged thirteen. The three boys inspected the tree. When one boy climbed up and touched the tackle-block it fell to the ground, shattering into a dozen pieces.
'Someone has been digging,' remarked one boy. Digging for what?' asked another. For treasure,' suggested the third. Or to bury treasure,' exclaimed the first boy.
Reared on a coast that was the legendary haunt of pirates, it did not take the boys long to return home, fetch picks and spades and start to dig beneath the tree. Shovelling out the loose earth, they found themselves in a thirteen ft. wide, well-defined circular shaft, its walls of hard clay scored by the marks of picks. At four ft. they unearthed a layer of flagstones. These were not indigenous to the island, but must have been brought from Gold River, about two miles distant.
At the depth of ten ft. they found a platform made of oak logs, extending across the shaft, their ends firmly embedded in its walls. The outside of these logs was so rotten as to suggest they had been embedded there for a great many years. They loosened the logs, hoisted them out and dug downwards. At twenty ft. they encountered another oak platform, and another at thirty ft. The earth between each platform had settled about two ft.
Realizing that the task was too much for them, McGinnis, Smith and Vaughan, leaving sticks to mark the spot, returned to the mainland to seek help in securing the treasure they were convinced lay a few feet further down. It took them nine years to find backers to provide the primitive machinery they required. The island, they were told, was haunted; a woman recalled that her mother, one of the original settlers in the district, had spoken of strange lights and fires at night. A boatload of men had rowed to the island to investigate and had never returned.
[...]
Work on the site was resumed in 1804, nine years having elapsed since the discovery of the mysterious shaft, the Money Pit', as it would soon become know.
The Colonist, 2 January 1864, records:

The late Simeon Lynds of Onslow, a man well known in many parts of Colchester County, at the time happened to visit Chester on business. As Lynd's father and Vaughan were related, he called and passed the evening with him. In the course of conversation during the night, Lynds was let into the secret of the Pit' on Oak Island, and the opinion entertained about it by Vaughan and his companions.
The next day Vaughan crossed over to the place with Simeon Lynds, in a boat, to let him pass his own judgement upon it. The result of Lynds' visit was that he became of Vaughan's way of thinking.
Lynds was then a young man (about thirty years) and his father (Thomas Lynds) was in comfortable circumstances, and he had a good many well-to-do friends. He concluded to go home, form a company among them, to assist the pioneers in the search after the treasure and to complete it.

Lynds formed a syndicate of friends from Halifax, Colchester and Pictou Counties: Colonel Robert Archibald, Captain David Archibald and Sheriff Thomas Harris.

On their arrival they were joined by the first three treasure seekers, with whom they made arrangements to commence operations.
During the time that had intervened since the leaving of work by the resident diggers, the Pit had caved in and formed the shape of a sugar loaf resting on its apex, and besides, from the action of the rain and weather, a great quantity of mud had settled at the bottom. It gave them some trouble to clear all this out, but when they had done so, they came across the sticks sunk in the mud by the first diggers on the termination of their work. They then felt satisfied that the place had not been interfered with since.
They had not got far into the work that was new to Vaughan and his former associates, when they struck a second tier of oak logs, corresponding with the first. Ten feet lower down they found a tier of charcoal, and ten feet further a tier of putty.

A small discrepancy appears to arise; in the account of the 1795 operations it is said that the boys encountered three oaken platforms at ten, twenty and thirty ft. levels, which they hoisted out, whereas by the Colonist's account it is implied that they did not reach the second and third tiers until 1804. [...] at the thirty ft. level the 1804 syndicate came upon charcoal (and) ten ft. below it, putty'. Another version states that the putty was found at the forty ft. level, spread over a platform of logs and there was so much of it that it served to glaze the windows of more than twenty houses around Mahone Bay. More charcoal and more oak logs were encountered farther down and ten ft. lower, coconut fibre and yet another oaken platform. Local tradition has it that quantities of coconut fibre were removed from the Pit. Hiram Walker, a ship's carpenter of Chester, who was engaged in the operations, told his grand-daughter, Mrs Cottnam Smith, that he had seen bushels of coconut fibre brought up from the shaft.
James McNutt, who worked on the island in 1863, and who wrote an account f which only a fragment survives, states that: At forty feet a tier of charcoal: at fifty feet a tier of smooth stones from the beach, with figures and letters cut on them; at sixty feet a tier of manilla grass and the rind of the coconut; at seventy feet a tier of putty.'
No authority other than McNutt mentions the tier of smooth beach stones with figures and letters cut upon them. [...] At the depth of ninety ft. it would seem the searchers uncovered a flat stone, three ft. long and one ft. wide, on the reverse side of which rude letters and figures had been cut. It was,' says McNutt, freestone, being different from any on that coast.' [...]The 1804 searchers do not appear to have wasted time trying to decipher the inscription, and they were unaware of the significance of its message, if indeed it had any meaning. Excited by the discovery, which seemed to herald the proximity of the treasure cache, they dug on feverishly. Thrusting a crowbar into the earth, which was becoming so soft and moist that they found themselves raising one cask of water to two of earth, they struck a hard, impenetrable substance at ninety-eight ft., which seemed to stretch across the width of the whole shaft. Some,' states The Colonist's account, supposed it was wood, and others called it a chest.'
It was close to nightfall on Saturday night. Convinced that they were on the brink of success, the elated treasure seekers climbed from the Pit, so filled with good spirits that they spent the evening discussing who would have the larger share of the treasure. When they returned the next morning, or more probably on the Monday, for the Sabbath intervened, they found sixty ft. of water in the Money Pit; it was flooded to within thirty-three ft. of the top. [...] Unfortunately for themselves and for the syndicate that followed them, the 1804 seekers did not stop to consider where the water came from. With the object of draining the Money Pit, they dug another shaft alongside it in the spring of 1805. Reaching a depth of 110 ft. they tunneled sideways in order to reach the chests they believed lay at ninety-eight ft. They were overwhelmed by a flood of water and they barely escaped with their lives. Overnight the second shaft filled with water, to within thirty-three ft. of the top.

That was the end of the first organized treasure hunt on oak island.

- Rupert Furneaux.