Bobby and Dad started digging a shaft in Smith’s Cove beach in an attempt to locate and block the sea water inlet tunnel. If they could stop the water, they would be able to search for treasure in the Money Pit area at their leisure. They spent each day in arduous physical labour, and at night they reviewed the day’s progress, discussed options, and debated theories of what was meant by various findings. During the long, cold winter nights of their first six months, they carefully reread every publication on Oak Island that they could find. They compared the information in those sources each with each other and related them to the signs of earlier expeditions that were still visible on the island. In this way they were able to calculate what lay where underground. This informed the direction of their work on the island.
It was like detective work. Every time they encountered previously dug earth, marker stones, timbers, or other objects, they tried to determine if they were part of work done by other treasure hunters or by those who had buried the treasure. They hoped to find the original work because that could lead them more directly to the treasure. However, other searchers’ work could be useful too; Dad and Bobby could add to that previous work or use it to calculate new directions for their own search. Conversely, whenever they encountered earth that had never been dug before, they knew they had gone beyond anything of interest.
Just living on an island presented special problems. They had neither electricity nor a telephone. They used propane lamps and stove; they rigged a battery charger, then charged a battery connected to an old car radio to listen to the news once a week. Obtaining food necessitated a trip to the mainland by boat, then a fifteen-minute car ride into Chester, where they kept a post office box and where the Shamrock Food Store supplied their groceries on a running tab, as it did for local fishermen. Phone calls for the family came in to a service station. Dad collected messages each time he went ashore. Return calls were made from a pay phone. Often letters or phone calls were of vital importance to their work. But whenever a call out was placed, it might be necessary to wait by the phone for the return call for long periods of time. Sometimes communications were missed. All of this was time-consuming and frustrating.
Large shipments of supplies were ferried to the island by a hired boat (usually Gerald Stevens’s Fury), but smaller supplies of lumber, machine parts, gas, and oil were brought to the island in the family’s outboard motorboat. Every journey to the mainland resulted in valuable time lost from what they considered to be their real work of searching for treasure. Once on the beach at Smith’s Cove, supplies needed to be carried up the steep hill to the flat grassy plateau that held the Money Pit.
After the first six months on the island, Bobby began a daily journal of the work. Many of us would try to keep a journal in circumstances as extraordinary as these, but most of us would eventually miss a day or two, and then another, until gaps outnumbered entries and we finally gave up. But Bobby never gave up. There is a journal entry for every day from March 20, 1960, to August 17, 1965, the end of his search.
The rhythm of island life comes through clearly in Bobby’s journals. The following entries were written that first winter, when my mother was in Ontario with Rick, and Dad and Bobby worked alone on the island.
Sunday, March 20, 1960
Gerald Stevens brought fuel oil and gasoline to island, and planks and barrels to Grandall’s Point. Made barrel bungs tight.
Monday, March 21, 1960
Built raft in 2–3 hours with 12 barrels, 6 logs, 27 planks, wire and nails. Loaded Plymouth and it floated like an iceberg (sank to plank level) to Smith’s Cove with speedboat. Very slow going. Towed it back to Grandall’s Point and staked it down so it floats at high tide and is dry at low tide.
Tuesday, March 22, 1960
Got 8 more barrels from Mader and trucked them to Grandall’s Point. Extra buoyancy needed for 5,000 lb. compressor. Did odds and ends rest of day.
Wednesday, March 23, 1960
Cleared everything out of compressor that wasn’t nailed to the floor. Fixed barrel bungs to be watertight. Sudden wind and we beached boat and puttered around with odds and ends that needed attention.
Thursday, March 24, 1960
Rigged braces for hoist at beach. Took hoist car from main pits and mounted in beach hole. Pumped out hole and started clearing ice and snow. Made record run to Chester. Uncovered and launched boat, scooted 2 1/2 miles to Chester by water, got mail, some groceries, newspaper and pics at drugstore, roared back and pulled up and covered boat in 45 minutes flat.
Friday, March 25, 1960
Cleared out beach hole. Set up generators and charged batteries.
Saturday, March 26, 1960
Put eight barrels under raft. Went to Chester by boat. Nearly drowned and froze coming back in 4 to 6 foot waves. Cold today. Seawater froze to deck.
Sunday, March 27, 1960
Cut poles to crib beach hole. Took them to Smith’s Cove.
Monday, March 28, 1960
Moved raft from Grandall’s Pt. to Government Wharf in Western Shore. Stored planks for loading it in gas station by dock.
Tuesday, March 29, 1960
Loaded compressor and towed it over and unloaded at Smith’s Cove. Took raft apart and stacked up barrels, planks, and logs.
Wednesday, March 30, 1960
Went to Chester and here and there. Got winch welded up. Rained all afternoon, got completely drenched coming back.
Thursday, March 31, 1960
Took barrels to Andy’s. Built runway and platform over hole and cleared out three wheelbarrow loads of sand, using hoist and winch.
Friday, April 1, 1960
Cribbed one end of hole after cutting up poles and clearing sand and building loading platform in hole. Rained most of afternoon.
Saturday, April 2, 1960
Went to Chester and returned barrels. General running around used up the day.
Sunday, April 3, 1960
Cleared out stones and sand (about ten hoist loads) and cribbed far end of beach hole toward the point.
Monday, April 4, 1960
Dug hole 6” deeper for pump.
Tuesday, April 5, 1960
Fixed part of caved-in cribbing near pump. Briggs and Stratton got a seized valve and we fixed it (luckily). Found two old beams just seaward of our cribbing. They are vertical, about 6” or 8” by same. Very old and rotten. Apparently part of an old cribbing. Later noticed 8” x 1” boards in a square shape at least 5’ long. Some kind of hollow post or trough.
Wednesday, April 6, 1960
Dug beach hole deeper. Went to Chester and wasted day getting Chappell [on phone].
Thursday, April 7, 1960
R.E. [Dad] went to Halifax to see Chappell. Met Harris [R.V. Harris, author of The Oak Island Mystery] and others.
Friday, April 8, 1960
Went to Chester. Learned a lot about the Teazer. One fellow will show us where it went down. Finished fixing cribbing.
Saturday, April 9, 1960
Deepened