The privately owned Oak Island spans 140 acres off Nova Scotia's southern shore in Lunenburg County. The island is one of Mahone Bay's around 360 small islands. Located about 200 meters from the coast, the tree-covered island is connected to mainland Canada by a causeway and gate. There are several stories of possible buried historical artifacts or treasure, as we well as explorations to find it associated with Oak Island.

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Chester village is the closest community to Oak Island. The area's earliest European residents were fishermen from France, who had built homes on the land that would become Chester by the 1750's. The British government, through a series of measures, encouraged New Englanders to settle in the area during the Seven Years' War. The village of Chester was officially founded in 1759.

In 1761, the first major settler group arrived from Massachusetts in the Chester area. Oak Island was separated into thirty-two lots the next year, each containing four acres. The island was originally known as "Smith's Island" during the early days of British settlement, named after Edward Smith, an early settler. The island was renamed "Gloucester Isle" by Joseph Frederick Wallet DesBarres, a cartographer, in 1778. It wasn't too long after that the local name of "Oak Island" officially become the island's name. The government issued more land grants that included sections of Oak Island in 1784, however, this time it was to former soldiers.

A causeway was built from Oak Island's western end to the mainland's Crandall's Point by Robert Dunfield in 1965. Today, the majority of the island is now owned by Oak Island Tours, owning seventy-eight percent of Oak Island. The remaining portion of the island is split between other private parties. There are now only two permanent cottages and two homes are located on the island, and these are only occupied part-time.

Investigations, excavations, and treasure hunts have occurred on Oak Island for over a century and a half. Several theories exist about what is possibly concealed or buried on the island, if anything at all. Areas on the island thought by some to have treasure are the Money Pit, the beach at Smith's Cove, a swamp in the shape of a triangle, and Nolan's Cross, a boulder formation. Repeatedly excavated, critics of the treasure stories believe there is no treasure in the Money Pit area, and that it is nothing more than a natural phenomenon.

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The first widely held story of the Money Pit began with a man thought to be the first settler on Oak Island. Around 1799, this man, named "McGinnis," discovered a "depression" in the ground while he was looking for a location for his farm. Other early settlers of the island brought along a story of a dying sailor belonging to the crew of Captain William Kidd, claiming that a treasure valuing two million pounds had been buried on the island. McGinnis believed the depression he found was consistent with the story of the sailor with Captain Kidd, so sought help and began to dig. Since then, many other treasure hunters and companies have attempted to find treasure in the Money Pit area.