1861
- April 3
- The Oak Island Association syndicate is formed, based on the Truro syndicate. Included are Adam Tupper, Jotham McCully, James McNutt, Jefferson McDonald, Samuel Retti, and George Mitchell. They make a deal with land owner Anthony Graves, to give him one-third of any treasure recovered. The company issues 100 shares at $20 each. [3.45] [4.48]
- (month unknown)
- The Oak Island Association resumes the search. The Money Pit is cleared to 88 feet, encountering no water. A new shaft (5B) 25 feet away is dug to 120 feet, with no sign of the flood tunnel. [1.194] [3.43,45] [4.48]
- Another shaft (No. 6) is dug 18 feet west of Money Pit. At 118 feet, a horizontal tunnel toward the Money Pit is started. At 17 feet toward the main shaft. water and mud again rush in. A pumping gin is employed, but stopped after three days pumping with no progress in keeping the water out. [3.43,45] [4.50]
- A tunnel is dug from the 120 foot shaft, 25 feet away from the Money Pit. Again, as they get close to the main pit, uncontrollable water rushes in. They try bailing the three shafts using four 70-gallon buckets with all 63 men and 33 horses. They abandon this after a couple days. [4.50]
- Two men go into a connecting tunnel toward the Money Pit to clear out the mud. A big crash is heard, the men barely escape, and water rushes in. The water level is lowered again, then another big crash is heard, then collapse of timbering within Money Pit, leaving only the upper 30 feet. Now, the bottom is sounded at 102 feet, 14 feet lower than previous. Some artifacts are recovered from the inrush of debris, but no treasure. Artifacts recovered: bottom of yellow painted barrel or dish, stick of oak timber 3.5 feet long, piece of juniper with bark on and cut at each end, spruce slab with mining auger hole in it. [3.43,45] [4.50]
- The Oak Island Association raises another $2000. [4.53]
- September 30
- The Nova Scotian has an article on recent digging. [3.43]
- (month unknown)
- (Fall) The Oak Island Association sets up a cast-iron pump and steam engine. A boiler of a pump bursts, scalding one man to death and injuring others, the first death recorded since first digging in 1795. Work is halted for the winter. [3.46] [4.53]
1862
- (month unknown)
- (Spring) The Oak Island Association digs a shaft (No. 7) close to the west of the Money Pit. It is dug to 107 feet, using a pump to keep it free of water. Then the Money Pit is dug and sides cribbed to 103 feet, but pumping cannot keep up with water to dig further. [3.46] [4.54]
- A new shaft is dug inland from Smith's Cove, down to 50 feet, no flood tunnel found. Tunnels are dug from the bottom in various directions, but encounter no flood tunnel. [4.54]
- The box drains of Smith's Cove are uncovered and 30-40 feet are removed and packed full of clay. This reduces the water flow into the Money Pit, but the sea soon clears out the clay. [3.47] [4.55]
- October 16
- The Liverpool Transcript includes a letter by J.B. McCully indicating the pit contained layers of oak timber at 10, 20, and 30 feet. [3.20]
1863
- (month unknown)
- Shaft 9 is dug, 100 feet east of the Money Pit, 20 feet south of the assumed line of the flood tunnel. They dig down to 120 feet, then dig toward Smith's Cove in search of the flood tunnel. Another tunnel is dug toward the Money Pit, reaching it at the 108 foot level. The Money Pit is cribbed to 108 feet, and tunnels are dug from that level in search of treasure. [1.196] [3.47] [4.54]
1864
- January 2
- Halifax newspaper The Colonist reports Dan McGinnis found oak logs at 10 feet, then dug 15 feet more. [3.20] [4.198]
- (month unknown)
- Tunnelling continues, finally finding the flood tunnel where it enters the Money Pit around 110 feet. Water floods in, but pumps conquer it. The tunnel is 2.5 feet wide, 4 feet high, filled with round stones, intersecting the Money Pit at an incline of 22.5 percent. Its identity is verified with clay dumped into cove, arriving in 30 minutes. The company is now out of money, so ends operations. [1.196] [3.50] [4.56]
- The stone slab with encrypted message is removed from John Smith's fireplace, and placed in the window of bookbinder A&H Creighton in Halifax, Nova Scotia. The stone is exhibited there to help sell shares in a treasure seeking company. [3.30] [4.20]
1866
- March
- The Oak Island Association cedes rights on the island to the Oak Island Eldorado Company (later called the Halifax Company). [3.47]
- May 3
- The Oak Island Eldorado Company is formed. They sell 200 shares at $20 each. Plan is to build wood and clay dam around Smith's Cove, pump out water, completely cutting off the flood tunnel. [4.56]
- (month unknown)
- The Oak Island Eldorado Company builds a 375 foot long 12 foot high dam of wood and clay at Smith's Cove. The dam fails to keep water out of the Money Pit, and the sea quickly destroys the dam. [1.195] [3.49] [4.56]
- November 26
- (to January 7, 1867) The Money Pit is cleared to 108 feet, and continuous pumping keeps the water level low. A drill is set at the 90 foot level. Drilling hits spruce wood at 110 feet. At 128 feet, borings include coconut fiber, wood chips, and charcoal. At 132 feet, oak borings, chips of spruce or poplar, and coconut fiber. At 158-163 feet, all holes hit hard reddish marl natural to the island. [1.195] [3.50] [4.57]
1867
- (month unknown)
- The Oak Island Eldorado Company discontinues operations. [3.52] [4.57]
1878
- (month unknown)
- (Spring) Sophia Sellers (daughter of Anthony Vaughn) plows a field on Lot 19, between the Money Pit (350 feet east of it) and Smith's Cove. Her oxen team falls in a well-like hole as the ground collapses, 15-18 feet deep, 6-8 feet across. This becomes known as the Sink Hole or Cave-in Pit. [1.196] [3.52] [4.59]
1885
- (month unknown)
- A boatswain's whistle of ancient design, made of bone or ivory, is found in the soil below high tide on the shore of Smith's Cove. [3.53] [4.60]
1887
- (month unknown)
- Anthony Graves dies. His daughters Sophia and Rachel inherit his property. [3.52] [4.61]
1890
- (month unknown)
- (approximate year) A copper coin weighing 1.5 ounces is discovered on the island, dated 1317 or 1713. [3.53] [4.60]
1893
- (month unknown)
- Frederick Blair and S.C. Fraser form the Oak Island Treasure Company. The company is incorporated in State of Maine. President A.M. Bridgman, treasurer H.C. Tupper, and directors George Houghton and C.C.L. Moore. The company leases the land of Oak Island for three years for $30,000, with the rights to everything recovered. The company issues $60,000 of shares at $5 per share. [1.196] [3.54] [4.60]
- December 26
- The Boston Traveller publishes a story by J. Edward Wilson. Wilson claims that in 1866 he received a map, found in 1826, of treasure on an unnamed island on the south-east coast of Nova Scotia. He says a shaft was dug by an oak tree, with a tunnel at the bottom of the shaft leading to sea level. The shaft was filled with no treasure. Instead the treasure was buried a certain distance away only 20 feet below the surface. [4.98]
1894
- January 3
- The Halifax Evening Mail also publishes the article by J. Edward Wilson. [4.98]
- June
- The Halifax Chronicle-Herald newspaper runs an article noting two workers barely escaped death from rocks falling on their heads when a hoist drops a load down a shaft. [4.65]
- (month unknown)
- (Summer) Blair and company excavate the Cave-in Pit (shaft 11) down to 52-55 feet, noting the original pit was 6-8 feet diameter with pick marks on walls, and loose fill. Salt water is encountered, and can not be kept pumped out; they conclude it is connected to the flood tunnel. [1.196] [3.54] [4.62]
1895
- April 2
- The Oak Island Treasure Company holds a meeting, appointing A.S. Lowden general manager for the coming summer. [4.63]
- (month unknown)
- (approximate year) A new shaft, number 12, is started 30 feet east of the Money Pit, 8 feet north of the presumed flood tunnel. At 55 feet down, they dig a horizontal tunnel south. The flood tunnel is not found, now known to be 40-50 feet deeper. [3.54] [4.63]
- (approximate year) Another shaft, number 13, is started 25 feet north of the Cave-in Pit. At 82 feet, a horizontal tunnel is dug heading south, looking for the flood tunnel, but it is not found. [3.56]
- Mining engineer Adam Tupper (or A.S. Lowden) directs a direct assault on the Money Pit, but they erroneously excavate Shaft 3, 10 feet northwest of the main pit. Digging gets down to 55 feet, then pumping cannot keep up with water. [3.56] [4.63]
- June 19
- S.C. Fraser writes about his work in 1866 as foreman. [3.51]
- November
- The Oak Island Treasure Company holds a meeting, appointing a new board of management: manager: T. Perley Putnam, treasurer Frederick Blair, George Fullereton, W.H. McDonald, William Chappell, and director of operations Captain John William Welling. [4.64]
1896
- October
- Work on the Money Pit resumes, pumping it dry, and clearing down to 70 feet. But at this depth, pumping can't handle the water flow. [4.65]
- (month unknown)
- The 75-foot shaft of 1850 near Smith's Cove is deepend to 78 feet, but then water rushes in. [4.65]
1897
- March 26
- Maynard Kaiser is killed when a hoisting rope slips off a pulley, dropping him down a shaft. [3.57] [4.65]
- April 22
- Digging in the presumed Money Pit gets down to 110 feet, when they find a tunnel dug in 1860s. Following the tunnel leads to the real Money Pit. They clear the Money Pit down to 111 feet, finding the 2.5-foot wide opening in the east wall, the flood tunnel. The sides and top are cut from solid clay, filled with beach stones, gravel, and sand. [3.56] [4.66]
- June
- Work stops on the main pit, pumps fail, and the water level raises back up to sea level. [3.57]
- (month unknown)
- Water-diviner Chapman from Medford, Massachussetts maps various tunnel positions. [3.57]
- The Oak Island Treasure Company drills to 153 feet, then encounters 7 inches of soft stone, 5 inches of oak, then perhaps soft metal. Drill operator William Chappell finds traces of gold on the drill, but keeps it a secret. [1.171]
- Five small holes, 15 feet apart, along a line 80-95 feet are drilled 50 feet inland from high tide on Smith's Cove. Only the center hole reaches salt water at 80 feet. Each hole is loaded with 50-75 pounds of dynamite, and blown up. No great effect. 160 pounds detonated in the middle hole causes water in the Money Pit and Cave-in Pit to foam and bubble. [1.197] [3.57] [4.66]
- Captain Welling discovers a triangle of stones near the high water mark of the south shore. [4.112]
- Assuming the flood tunnel is now clogged from the dynamiting, work commences on the Money Pit. Water is pumped out down to 100 feet, and a platform and drill are set at the 90 foot level. The first drilling hits oak at 126 feet, for 5 inches, then hits iron, can't drill through it. [1.197] [4.68]
- The second drill hole is made 1 foot from the first. Drilling gets to 153 feet 8 inches, then hits soft stone or cement, 7 inches thick, then 5 inches solid oak. Then a 1.5-2 inch gap, then through some unnamed substance. Further drilling in this hole encounters metal in pieces, then the same undrillable iron near 154 ft. Borings brought up include oak chips, coconut fiber, and other bits that will be examined later. [1.197] [4.68]
- The third drill hole strikes wood at 122 feet, then cement at 153 feet. Then the drill runs between wood and cement for 4 feet, and cement alone another 3 feet, to a depth of 160 feet. Then an iron barrier is struck at 171 feet. Drilling for two hours only gets 1/4 inch into the iron. Borings checked with a magnet confirm iron cuttings. [4.68]
- The fourth or fifth hole hits water, pumped out at 400 gallons per minute, probably a link to the sea. [4.68]
- At the Court House in Amherst, Dr. A.E. Porter studies with a magnifying glass recent borings brought up from drilling. He discovers a tiny fragment of parchment with writing, possibly showing "vi", "ui", or "wi". [1.197] [4.68]
- (approximate year) Experts in Boston examine the tiny piece of parchment, confirming the material and that it is inscribed with India ink written with a quill pen. [1.197] [4.68]
- (approximate year) Two samples of the cement material encountered in drilling in the Money Pit are sent for chemical analysis in London, England. Analysis reports that both are (approximately) 37% lime, 33% carbonate, 13% silica, 10% iron and alumina. The chemists state that they believe "it is cement which has been worked by man". [4.71]
- October
- A new shaft is started 40 feet south of the Money Pit, with the intention of digging to 175 feet, then tunneling under the iron, and using this shaft to pump out water while digging further in the main pit. At 95 feet, salt water breaks in at the 70 foot level from a tunnel dug in the 1860s. [4.72]
1898
- January
- A new shaft is started 35 feet south-west of the last shaft, 80 feet from the Money Pit, with the same goal of digging under the iron obstacle. [4.72]
- April 1
- At 160 feet in this new shaft, salt water through a seam of sand becomes unmanageable. Pumping is useless, and this shaft has to be abandoned. [4.72]
- (month unknown)
- Four more shafts are dug, all failing in the goal of tunnelling under the Money Pit. [4.72]
- April
- Over three months, tests are made of the water in the shafts. Water is pumped into one of shafts, resulting in muddy water showing up at three widely separated places near low tide of the south shore, but no muddy water at Smith's Cove. Similar results when pumping water into the Money Pit. Dynamiting a south shore inlet results in muddy water in the Money Pit. [1.197] [4.72]
1899
- October
- The Money Pit is doubled in size, with a second shaft 5 feet by 8 feet excavated beside it on the west side. By 113 feet, the pumps are overwhelmed by the quantity of water present. [1.198] [4.72]
1900
- (month unknown)
- More drilling in the main shaft is done, to explore the presumed cement chamber. However, this time only boulders are encountered. [4.73]
- May
- Most assets of the Oak Island Treasure Company are sold off. [1.198] [4.73]
1901
- (month unknown)
- Another whistle, this one shaped like a violin, made of bone or ivory is found on the shore of Smith's Cove. [3.53]
1905
- (month unknown)
- Frederick Blair obtains a 40 year Mining Lease for the Money Pit site. [1.198]
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