The earliest human occupation of the region dates back several thousand years to the ancestors of the Mi'kmaq, an indigenous First Nations people of Canada's Atlantic Provinces.
Europeans established permanent settlements in the area during the mid-18th century through the Shorham grant, an edict which offered free land grants to attract settlers and generate population growth.
At the time, Oak Island was known locally as "Smith's Island" (named for Edward Smith, an early settler), but was renamed to "Gloucester Isle" in 1778, and shortly after to "Oak Island" supposedly because of the red oaks growing on the island.
The following account is neither exact nor complete, but is a rough summary of the reports and materials published in sequence.
The history of the Oak Island treasure hunt begun in 1795, when a young Daniel McInnes discovered evidence of tree felling on the island's interior and a clearing with a shallow saucer-shaped depression.
McInnes likely envisioned stumbling across a pirate cache, as the Novia Scotia region was known to be a hide-out for pirates in the 17th and 18th centuries during the Golden Age of Piracy.
The most infamous pirate to be associated with the Oak Island legend is Captain Kidd, however, there is little supporting evidence other than hearsay, and any association is merely speculative.
McInnes returned to the island with John (Jack) Smith and Anthony Vaughan, and begun excavating the depression until they discovered a layer of flagstones sourced from the Gold River several miles to the north.
Upon removing the flagstones, it is claimed that the trio found a shaft made by human hands (evidenced by pick marks in the hard clay walls), and continued to excavate the shaft interior to reveal several platforms of wooden logs at a depth of every 10 feet.
This shaft would later become known as the "Money Pit".
At 50 feet, there was a layer of thick putty across another platform, and at 60 feet, a bed of eelgrass and non-native coconut fibres. Upon reaching almost 90 feet, the team supposedly found a square-cut flagstone inscribed a cipher, and by almost 100 feet, they struck a solid mass.
The cipher stone was examined by James Leitchi, a professor of languages at Dalhouisie University, who claimed that it read "Forty feet below, two million pounds are buried". Leithchi was a member of the Onslow company, so his motives have been questioned as to whether he fabricated the cipher to sell stocks in the company.
As night had set in, they retired until the next morning, only to discover that the shaft had filled in with water and had to start a new adjacent excavation. This second shaft reached a depth of 110 feet, before that also rapidly filled with water and they narrowly escaped with their lives. Over the next two years, the company attempted to drain the shaft but to no avail, and was forced to accept defeat after a third shaft also flooded.
Smith formed a new company known as the Truro Company, and returned to Oak Island in 1849. The expedition members tried a new approach by using a horse-driven pod auger to collect samples, which pierced the solid mass from before and dropped through a small 12 inch void.
The auger reached another platform, followed by different layers of loose metal pieces and wood. It is said that upon retrieving the auger to examine the sampling, it returned with three small links of chain gold (unconfirmed source).
The company returned the following year and excavated a new shaft, but as before, this started to flood once they reached the level of the solid mass. Upon realising that the water level rose and fell with the tide, the company members concluded that the Money Pit must be connected via an underground tunnel to draw in water from Mahone Bay.
They scoured the islands coastline and found five stone-walled box drains connected to a sump on Smith's Cove. Watching the rising water level during high tide, seawater entered the drains and filled the sump, which orientated towards the direction of the Money Pit.
At that instant, the realisation struck the company members: they were confronted with an intricate booby trap, built using advanced mining techniques and a sophisticated water management and drainage system.
A new attempt was made in 1871 with the Oak Island Association, but their shaft excavations caused the bottom of the Money Pit to collapse and flood, almost killing two men.
Another company, the Oak Island Treasure Company, took a different approach by first focusing their attentions on a site known as the "Cave-in-Pit", located 350 feet east of the money pit.
They speculated that this was the original ventilation shaft for the digging of the flood-tunnel connected to the sea, however, like all other endeavours before, this shaft flooded and was abandoned.
The Oak Island Treasure Company continued to operate for several years and used a rig to drill through the collapsed bottom of the Money Pit. Upon reaching 170 feet, the drill struck an impenetrable layer and was raised to reveal flecks of gold and a tiny scrap of sheepskin parchment bearing the letters "vi" or "ui" on the drill head.
By the turn of the century, various groups and startup companies attempted their hand at the treasure hunt, including the One Gold Salvage group, whose members included Franklin D. Roosevelt.
From between the 1909 to the 1990's, most of the activities involved clearing and draining existing shafts, however, William Chappel, former member of the Oak Island Treasure Company, sunk a shaft near to where the original Money Pit was located and found several artefacts, including an axe, a flute anchor, a pick, and remnants of an oil lamp.
To this day, many theories and interpretations of the Money Pit have been proposed. The most unlikely include a Masonic or Templar connection, or that it was constructed by French Army engineers to hide the treasury of the Fortress of Louisbourg after British forces captured the fortress during the Seven Years' War.
The more credible theories propose that the Money Pit and associated discoveries are the remnants of the regions industrial history, such as a tar or salt works. Between 1720 and 1722 (three years before McInnes first discovered the Money Pit), the South Sea Company actually operated on Oak Island and constructed large kilns for extracting tar.
However, according to some geologists, the Money Pit is simply a natural phenomenon such as a sinkhole or limestone cavern filled in with accumulated debris.
As for the "booby trap" that floods the shafts, in 1995, the Woods Hole Oceanographic Institution conducted a survey on the island and concluded that the flooding was caused by a natural interaction between the island's freshwater lens and tidal pressures in the underlying geology.
Even dating the Money Pit has contrasting results. Carbon dating of wood samples in a 1969 study by Geochron Laboratories Inc returned a result that corresponds to 1575, while a 1981 study by Brock University returned a result that corresponds to 1700 + 80 years.
The truth behind Oak Island and the Money Pit is one that may never be answered. Over the past two centuries, the island's landscape and topology has been drastically altered, and any date-able archaeological remains or objects have likely been displaced out of context by the treasure hunters.
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