| 1497 | John Cabot becomes first European known to have set foot on Nova Scotia; claims territory for England |
| 1602–1614 | Career of pirate Peter Easton, based on island of Oderin off coast of Newfoundland |
| 1604 | Samuel de Champlain establishes Port Royal on Bay of Fundy, laying the first French claim to Nova Scotia |
| 1605 | Acadians begin settling in Nova Scotia |
| 1632 | French establish LaHave settlement at entrance to Mahone Bay |
| 1670 | Henry Morgan sacks city of Panama; treasure haul is never accounted for |
| 1680–1699 | Career of privateer and pirate William Kidd; Kidd buries part of treasure seized from Quedagh Merchant on Gardiners Island in 1699 |
| 1687–1694 | Career of privateer William Phipps; Phipps sacks Acadian city of Port Royal in Bay of Fundy in 1690 |
| 1685 | Huguenots persecution begins in France; many sail to and settle in Nova Scotia |
| 1700 | French governor invites Atlantic Coast pirates to make LaHave their “depot” |
| 1713 | French found fortress of Louisbourg on Cape Breton; Louisbourg pay ships begin sailing Atlantic |
| 1745 | Louisbourg falls to British |
| 1746 | D’Anville fleet sails from France to take back Louisbourg; many ships lost at sea |
| 1756 | Governor Cornwallis expels Acadians from Nova Scotia |
| 1759 | Shoreham Grant brings influx of settlers to Mahone Bay from New England; Chester Township established |
| 1763 | Treaty of Paris permits Acadian return to Nova Scotia |
| 1765 | What will become Oak Island designated as Island No. 28 by Charles Morris, surveyor general of the Nova Scotia province; Morris divides island into thirty-two four-acre lots |
| 1768 | Anthony Vaughan Sr. immigrates to Mahone Bay area of Nova Scotia |
| 1781 | Two Vaughan brothers purchase lots 13 and 14 on Oak Island |
| 1783 | Freed slave Samuel Ball arrives in Canada and settles in Mahone Bay |
| 1784 | Donald Daniel McGinnis, father of Money Pit discoverer, awarded a Crown grant of one hundred acres near Chester Township |
| 1786 | Eleven-year-old John Smith moves onto Oak Island with family |
| 1787 | Samuel Ball purchases first of nine lots he will own on Oak Island |
| 1788 | Vaughans petition province of Nova Scotia for permission to cut and mill pine trees on the mainland |
| 1795 | Putative year of discovery of Money Pit by Daniel McGinnis, John Smith, and Anthony Vaughan; initial excavation of the Pit |
| 1795 | John Smith purchases lot 18 on Oak Island; whether this was before or after the discovery of the Money Pit is not known |
| 1795 | Daniel McGinnis marries Maria Barbara Saller in Lunenburg |
| 1797 | Daniel McGinnis’s son Johan baptized in Chester |
| 1804 | Onslow Company sails to Oak Island, begins second and more extended excavation of Money Pit; discovery of lot platforms, charcoal, coconut fiber, blue clay, and inscribed stone follow, as does flooding of Money Pit |
| 1805 | Onslow Company returns to Oak Island; unable to solve flood system problem |
| 1827 | Daniel McGinnis dies on Oak Island |
| 1845 | Truro Company formed |
| 1849 | Truro Company begins operations on Oak Island; discoveries include the chain “links” brought up by a pot auger from the Money Pit; also claim to have passed through “metal in pieces” while drilling at a depth of more than 100 feet in Money Pit; dig shaft no. 2 on the island’s east-end drumlin |
| 1849 | Anthony Vaughan gives his account of Money Pit’s discovery to Robert Creelman |
| 1849 | Truro Company drill operator James Pitblado disappears from Oak Island and Mahone Bay area, supposedly after having removed some unknown object from drill tip |
| 1850 | Truro Company returns to Oak Island, barging out a “two-horse gin”; digs shaft no. 3; after failing to solve flood system, company explores Smith’s Cove, where they discover man-made beach and five-fingered drain system |
| 1857 | John Smith dies |
| 1857 | Geologist Henry Poole observes and describes the Money Pit area |
| 1861 | Oak Island Association begins operations on Oak Island with sixty-three workmen; by the time they finish there are six shafts in Money Pit area; digging and tunneling results in collapse of Money Pit; burst boiler results in first death of Oak Island treasure hunt, name of victim not known |
| 1862 | Jothan McCully writes first article about discovery of Money Pit for Liverpool Transcript |
| 1863 | Andrew Learmont Spedon’s Rambles among the Blue-Noses published, the first mention of Oak Island to appear between hard covers |
| 1863 | Inscribed stone is removed from Smith home to home of Jothan McCully |
| 1863 | Treasure hunter James McNutt writes a description of the early search for treasure on Oak Island; it is never published and only fragments of the manuscript are recovered |
| 1864 | Oak Island Association locates what they believe is the “flood tunnel” but operations on the island soon abandoned; by this point there are nine shafts in Money Pit area |
| 1864 | Jothan McCully (most likely) writes first published full account of Money Pit’s discovery for the Colonist |
| 1865 | Inscribed stone is removed from McCully home to be displayed in window of A. and H. Creighton in Halifax |
| 1866 | Oak Island Eldorado Company (soon to be the Halifax Company) formed; begins operations on Oak Island |
| 1867 | Halifax Company gives up treasure hunt on Oak Island |
| 1870 | Judge Mather Byles DesBrisay’s History of the County of Lunenburg originally published, the first description of the Money Pit’s discovery to appear between hard covers |
| 1878 | Sophia Sellers’s team of oxen falls into what will become known as the Cave-in Pit |
| 1885 | Ivory or bone boatswain’s whistle found at Smith’s Cove |
| 1893 | Frederick Blair establishes Oak Island Treasure Company in Boston |
| 1894 | Treasure Company begins operations on Oak Island; excavates the Cave-in Pit; digs shaft no. 12 |
| 1896 | Second edition of History of the County of Lunenburg published; in it DesBrisay replaces Samuel Ball with Anthony Vaughan as one of the Money Pit’s original discoverers |
| 1897 | Blair and Treasure Company dig shaft no. 13; Maynard Kaiser becomes second to die during treasure hunt on Oak Island; Captain John Welling and Treasure Company crew find man-made tunnel flowing with saltwater to Money Pit; scrap of parchment with writing in India ink pulled from bit of drill bit probing Money Pit; Treasure Company sinks six more shafts on east-end drumlin, bringing the total to nineteen; A. Boake, Roberts and Company of London identify substance removed from drill bit as primitive man-made cement |
| 1898 | Captain John Welling is first to discover stone triangle and drilled boulder; Treasure Company besieged by creditors and collapses, with many investors declaring bankruptcy |
| 1900 | Frederick Blair buys out all other shareholders in the Treasure Company |
| 1904 | Through an agent, Blair acquires forty-year lease on Money Pit under Nova Scotia Mines Act |
| 1909 | Captain Henry Bowdoin announces in a series of interviews with New York newspaper that he is taking over the Oak Island treasure hunt after striking a deal with Frederick Blair, forms Old Gold Salvage and Wrecking Company, sells only five thousand of 250,000 shares offered, ten to Franklin Delano Roosevelt; first claim made (in New York Times) that what is buried on Oak Island are the French crown jewels; Bowdoin begins operations on Oak Island, doing little of what he promised, quits the island in November, promising to return before end of 1911 |
| 1911 | After failing to make a deal with Frederick Blair to continue work on Oak Island, Bowdoin takes revenge by writing article for Collier’s magazine in which he claims there has never been any treasure on Oak Island and that flooding of the Money Pit is a naturally occurring phenomenon |
| 1912 | Blair answers Bowdoin’s article with one of his own written for the Amherst Daily News |
| 1912 | Professor S. A. Williams proposes solving Money Pit problem with Poetsch method but is unable to raise adequate funds |
| 1913 | Blair acquires eight-year lease on Money Pit lot from Sophia Sellers |
| 1919 | Creighton and Marshall bookbinding business closes and inscribed stone disappears, never to be seen again |
| 1921 | Blair makes deal with engineer Edward Brown to excavate the Money Pit, but Brown never gets deeper than 7 feet |
| 1922 | Blair posts advertisement in Boston Journal of Commerce for a partner in the treasure hunt |
| 1931 | Blair signs partnership agreement with William Chappell, the drill operator who brought up the parchment scrap; William’s son Melbourne helps him organize operations on the island; they sink shaft no. 21, broadest hole ever dug on Oak Island; among the artifacts they recover are an anchor fluke, an Acadian axe and seal-oil lamp; storms end work in October |
| 1932 | Blair loses lease on Money Pit property and it is acquired by engineer John Talbot on behalf of investor group headed by New York heiress Mary B. Stewart; Talbot accomplishes little, but does take the boatswain’s whistle to Stewart in New York, and it is never seen again |
| 1933 | Thomas Nixon, the first to suggest that the treasure of Tumbes is buried on Oak Island, signs deal with Blair to enclose Money Pit in steel pilings in order to excavate; instead he drills fourteen boreholes to bring up fragments oak and china |
| 1935 | Gilbert Hedden signs deal with Blair to take over the Oak Island treasure hunt, buys Money Pit property from Sophia Sellers’s heirs |
| 1936 | Hedden’s crew, under supervision of engineer Frederick Krupp, begins operations on Oak Island, opening and draining shaft no. 21, known as the Chappell shaft, find what they believe to be an original flood tunnel at a depth of 93 feet |
| 1936 | Exploring the island on his own, Hedden discovers the timbers of a structure built before the early 1700s at Smith’s Cove |
| 1937 | Captain Kidd and His Skeleton Island by Harold Wilkins published, containing what becomes known as the Mar Del map; Hedden writes to Wilkins, noting similarities to Oak Island |
| 1937 | Hedden and crew return to Oak Island, begin work on shaft no. 22, to be twice the size of Money Pit; Blair tells Hedden about stone triangle and drilled boulder discovered by Captain Welling in 1897; Hedden orders his men to search, and one of them, Amos Nauss, finds the triangle; Hedden also finds not just one drilled boulder, but a second as well; Charles Roper is brought to the island to conduct a survey using the reference points written on the Mar Del map; Roper discovers that medial line of stone triangle is pointing due north and right into the center of the Money Pit |
| 1937 | Hedden writes to President Roosevelt to inform him of the discoveries, then sets sail for England to meet Harold Wilkins; Wilkins confesses he created the Mar Del map but says he may have based it on the Captain Kidd treasure charts he saw at the British Museum |
| 1938 | Hedden is sued by the Internal Revenue Service, effectively ending his direct involvement in the Oak Island treasure hunt |
| 1938 | Professor Edwin Hamilton signs a deal with Blair and Hedden to take over the treasure hunt on Oak Island, begins boring operations that summer, putting down fifty-eight holes in Money Pit area, bringing up “very old oak” and what he believes are connections to the flood tunnel system; establishes that seawater is pouring into Money Pit area at rate of 800 gallons per minute; also establishes that Chappell shaft and Money Pit are just a few feet apart |
| 1939 | Professor Burrell Ruth writes to Hedden, making the first known claim that what is buried in the Money Pit are the manuscripts of William Shakespeare |
| 1940 | Hamilton and crew find Halifax Company tunnel |
| 1943 | Hamilton gives up efforts on Oak Island, having proved mostly how difficult the previous work on Oak Island makes any future progress |
| 1944–1946 | Blair negotiates failed deals with Anthony Belfiglio and Edward Reichert |
| 1947 | System of tunnels and vaults reportedly found on Haiti by engineer Albert Lochard |
| 1948 | Hedden agrees to sell his property on Oak Island to Colonel H. A. Gardener, who proposes to explore the Money Pit with a radio scanner developed by US military; Blair blocks the sale |
| 1949 | Hedden does sell his Oak Island lots to petroleum engineer John Whitney Lewis; Lewis, however, learns that Frederick Blair has reacquired treasure trove rights and agrees to sell the same lots to Melbourne Chappell |
| 1951 | Frederick Blair dies after more than a half century of involvement in the Oak Island treasure hunt, leaving behind the documents that establish the history of operations on the island; Mel Chappell acquires Blair’s treasure trove license, making him the first to both own the Money Pit property and the right to search for treasure there |
| 1951 | Edward Rowe Snow’s True Tales of Buried Treasure is published, includes first claim of translation of inscribed stone by an Irish schoolmaster and first account of men “silhouetted against bonfires” being seen on Oak Island before the Money Pit’s discovery |
| 1953 | Thomas Penn Leary self-publishes his book The Oak Island Enigma, arguing that Francis Bacon or his followers were behind the works on the island |
| 1955 | George Greene makes deal with Mel Chappell to apply oil drilling methods to probe of Money Pit area; locates a large underground cavity at 45 feet belowground, finds that 100,000 gallons of water won’t fill it |
| 1956 | Greene writes to Chappell that he won’t be able to return to Oak Island that spring as promised; he never sets foot on the island again |
| 1957 | Robert Restall and Mel Chappell exchange letters, nearly make an agreement, but Chappell changes mind |
| 1958 | Chappell makes a deal with Harman brothers, professional drillers who begin probing Money Pit, bringing up oak and spruce fragments, coconut fiber, and ship’s caulking; Chappell refuses to renew their lease |
| 1958 | R. V. Harris’s The Oak Island Mystery is published |
| 1959 | Chappell signs first of several one-year agreements with Robert Restall, who along with son Bobbie sets up camp on Oak Island |
| 1960 | Restall’s wife, Mildred, and younger son, Ricky, move onto the island; Robert Restall and Bobbie explore south shoreline where Bob finds “1704 stone” |
| 1961 | Restall searches for “mystery box” in swamp, cannot locate it, also discovers the triangle of piled stones on slope of island’s east-end drumlin |
| 1962 | David Tobias becomes a Restall investor |
| 1962 | Fred Nolan completes first survey of Oak Island, approaches Chappell with offer to lease search rights in Money Pit area; Chappell refuses |
| 1963 | Nolan acquires seven disputed lots on Oak Island, reapproaches Chappell, offering to trade his lots for right to excavate Money Pit; Chappell refuses; Nolan excavates two shafts on own property |
| 1965 | Robert Dunfield becomes Restall investor |
| 1965 | Restall and crew open new shaft between Cave-in Pit and Money Pit; on August 17, Robert Restall, Bobbie Restall, Cyril Hiltz, and Karl Graeser die in that shaft |
| 1965 | Robert Dunfield takes over operations under the Restall contract; Mildred and Ricky Restall are moved off the island to house on mainland; Dunfield builds causeway connecting Oak Island and mainland, uses it to haul across the seventy-ton digging crane he will use to perform massive excavations at the Money Pit area and at Smith’s Cove |
| 1965 | Dan Blankenship joins treasure hunt as Dunfield investor, begins research at Nova Scotia Archives |
| 1965 | Reader’s Digest publishes article on Oak Island |
| 1966 | Nolan purchases quarter acre of land next to causeway entrance at Crandall’s Point |
| 1966 | Robert Dunfield abandons operations on Oak Island |
| 1967 | Dan Blankenship assumes control of operations on Oak Island, in association with David Tobias; Blankenship and Tobias make deal to include Fred Nolan; on island’s south shore, Blankenship finds handwrought nail and washer |
| 1967 | Tobias persuades Chappell to permit Becker drilling program that will establish basic facts of Oak Island’s underground structure; Canada Cement LaFarge identifies cement pulled from belowground as type common in sixteenth and seventeenth centuries; wood brought up is carbon-dated to be at least two and a half centuries old; beneath Hedden shaft, Becker drill finds holes filled with layers of small stones and blue clay putty; on basis of Becker program, Blankenship and Tobias announce they have proved the existence of man-made tunnels at depths of more than 200 feet beneath the surface of Oak Island |
| 1967 | Fred Nolan opens his Oak Island museum at Crandall’s Point |
| 1969 | Tobias, Blankenship, and investor group form Triton Alliance; Fred Nolan accuses Blankenship and Tobias of breach of contract, blocks entrance to causeway, forcing Triton to build a bypass; Triton retaliates by blocking causeway access to Oak Island, forcing Nolan to travel by boat; Nolan retaliates by blocking roadway through his property to Money Pit |
| 1969 | Borehole 10X is first drilled; cofferdam at Smith’s Cove permits Triton to expose a huge U-shaped wooden structure offshore; carbon-dating establishes structure was built prior to 1720; Blankenship also discovers the “G stone” near the Cave-in Pit |
| 1970 | Steel Company of Canada issues report stating that metal pulled from 10X is pre-1700 wrought iron |
| 1970 | Professor Ross Wilhelm produces his translation of inscribed stone and claims that Oak Island was used as a depot for storm-damaged Spanish ships in sixteenth century |
| 1970 | Tobias sends Blankenship to Haiti to find the pirate bank Albert Lochard claimed to have found in 1947; Blankenship can’t locate it |
| 1971 | Borehole 10X is widened and lined with 27-inch diameter casing; Steel Company of Canada reports that new metal fragments removed from 10X are case-hardened steel, most likely pre-1750 |
| 1971 | Fred Nolan acquires his own treasure trove license; Triton responds by making a new agreement with Nolan for a share of any treasure found on his property in exchange for Nolan’s right to drive across causeway and a promise not to challenge his ownership of disputed lots |
| 1972–1976 | Blankenship makes a series of dives to bottom of 10X |
| 1973 | Jane Blankenship moves to Mahone Bay |
| 1975 | Blankenships acquire lot 23 on Oak Island, begin building home there |
| 1975 | Engineering operation supervised by George Young finds cavern 52 feet deep at Western Shore, directly across from Oak Island |
| 1976 | Dan Blankenship nearly crushed by collapsing casing in 10X |
| 1976 | Blankenship and Tobias form Oak Island Tours |
| 1977 | Mel Chappell sells all of his land on Oak Island to David Tobias |
| 1978 | Blankenship begins using railroad tank cars to case 10X, assisted by Dan Henskee |
| 1979 | Blankenship first discovers “ice holes” off the south shore of Oak Island; dispute opens between Blankenship and Tobias about trying to seal south shore holes and about continued exploration of 10X |
| 1981 | Fred Nolan first finds the five cone-shaped boulders that constitute what will become known as Nolan’s Cross |
| 1983 | Triton files a lawsuit against Fred Nolan, alleging he is not legal owner of the disputed seven lots on Oak Island |
| 1985 | Triton/Nolan lawsuit goes to trial; Nolan prevails with ruling he is legal owner of seven lots on Oak Island |
| 1986 | Blankenship/Tobias relationship ruptures when Blankenship refuses to support Triton “big dig” plan for exploring Money Pit area, insisting they should concentrate on 10X |
| 1987–1988 | Blankenship and Dan Henskee replace tank cars in 10X with reinforced concrete |
| 1990 | Blankenship resigns from Triton board; Canadian government rejects Triton loan guarantee request |
| 1991 | Fred Nolan brings surveyor William Crooker to Oak Island to confirm his measurements of the large cross laid out on the island |
| 1992 | Discovery of Nolan’s Cross is announced in Crooker’s book Oak Island Gold; Nolan and Crooker suggest that the treasure taken in the 1762 sacking of Havana is buried on Oak Island |
| 1995 | Woods Hole Oceanographic Institution conducts detailed groundwater study of Oak Island |
| 1996 | Bedford Institute scientists conduct bathymetry study of Oak Island, discover two apparently man-made “scours” in ocean floor off south shore |
| 1997 | Bedford Institute scientists return to Oak Island, confirm existence of man-made “scours” |
| 2003 | Blankenship and Tobias accuse one another of planting newspaper story that Oak Island Tours will sell its Oak Island property for $7 million |
| 2003 | Petter Amundsen performs first excavations on Oak Island |
| 2004 | Rolling Stone article on Oak Island is published |
| 2005 | Oak Island Tours puts Oak Island property (78 percent of island) up for sale |
| 2007 | Rick and Marty Lagina see ad offering David Tobias’s Oak Island holdings for sale; Laginas first purchase lot 25, then make a deal with Tobias to purchase the rest of his Oak Island property, becoming equal partners with Dan Blankenship in Oak Island Tours |
| 2013 | Production of The Curse of Oak Island commences |