160 years ago, a terrible gale hit Trial Bay wrecking two sailing ships and driving another one onto the beach. The loss of three lives on the night of 2 June 1864 is commemorated on the obelisk at Point Briner, to the south of Horseshoe Bay.
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Normally a harbour of refuge, Trial Bay offered little shelter to the ships that night as the south westerly gale suddenly veered to eastward.
The ketch Wolloomooloo, under Captain Frederick White, had set out from Trial Bay the day before carrying a full cargo of maize and sundries for Sydney. She got as far as Point Plomer when the storm struck, forcing her to return to Trial Bay.
There she was tipped onto her beam ends by the gale and all four crew members were washed overboard. Able Seaman William Hawdon was thrown on shore by the heavy seas and was the only survivor.
Drowned were Captain Frederick Stephen Wright, French seaman Louis Laine of Brittany and seaman Frederick Woodward Ellis. It was Frederick Ellis' twenty-seventh birthday.
About a quarter of a mile south, the schooner Julia, also with a full cargo bound for Sydney, was sheltering in Trial Bay when the storm hit. Her anchors slipped and she was driven high onto the beach. The crew were able to reach land safely.
The third ship, another schooner named Gazelle, attempted to leave the Bay but was driven ashore to the north of the Woolloomooloo. Fortunately all hands were saved although the ship was a total wreck.
The owner of the Woolloomooloo, Thomas Hubbard, together with John McElhone, and Frederick White's sister, Mary Jane Cullen, subscribed to erect a stone obelisk on Point Briner as a memorial to the fatal sinking.
The stone sections for the monument were shipped from Sydney to Rainbow Reach where they were unloaded into rowing boats to be taken to the site.
After sustaining severe weathering over the years, the sandstone monument was restored in 1982. The monument carries a dedication to the three men drowned, and also some lines from Henry Kendall's poem "God Help Our Men at Sea".
It was the first man-made structure in South West Rocks.
In 1959, fishermen were trawling for prawns off Horseshoe Bay when their lines were fouled by a large barnacle encrusted anchor. Winched ashore, the anchor was two metres long and weighed half a tonne. A smaller anchor was also seen in the same locality and later recovered. Both anchors were thought to have come from the Woolloomooloo.
The two anchors were presented to the Macleay River Historical Society.
In 1965, the larger anchor was set up in Monument Park, at the bottom of Prince Street, South Kempsey as part of a memorial to shipbuilders and shipping men of the Macleay River. The smaller anchor is now in the shipping display at Kempsey Museum.