From a 1964 Gazette Column by Joseph Chase Allen:

There are inhabitants of the Island, especially of Vineyard Haven, who can recall a rather tumbledown but relatively large wharf far down the shore below the town’s present small boat basin.

Those who remember this dock will also recall that it was weighted down by scores of rusty, barnacle-encrusted anchors. There were anchors in that collection which would weigh a ton or better, and from that size on down to small specimens of ground-tackle. This pier and its burden were the final remains, a memorial in fact, of what had once been the lucrative business of anchor-dragging.

Anchor-dragging, or sweeping, was a seasonal and part time business followed by some owners of small vessels. It consisted in locating anchors lost by vessels, raising and securing them, and eventually restoring them to owners, when possible, or selling the anchors to others. Generally speaking, anchor-dragging was regarded as a sound and paying business.

It should be borne in mind that this business was intimately connected with the sailing ship era, and that in its heyday there were literally hundreds of sailing vessels moving to and fro past Vineyard Haven through Vineyard and Nantucket Sounds and across the shoals to the eastward.

There were many occasions when such sailing vessels were obliged to anchor. Baffled by head winds or the lack of any wind whatever, perhaps uncertain of their position because of fog or thick, driving snow, masters would take a sounding, and finding sufficient water or establishing their position as being safe, they would anchor and wait for the weather to clear, the tide to turn, or the wind to breeze. All this was routine procedure with all.

But while it was always the intention of a shipmaster to raise his anchor when again he sailed, this was not always what occurred. Sometimes vessels parted their chain cables in gales, and the anchor and part of the chain were lost. Conditions sometimes compelled a master to “slip his cable,” which meant knocking loose a shackle-pin and abandoning his anchor. There were also wrecks, when vessels foundered and sank, or drove ashore and were broken up by surf or wreckers, leaving anchors somewhere in the deeper water where they had failed to hold the storm-tossed crafts.

These were the incidents which attracted the professional anchor-draggers. Leave it to them to know just where, when and why an anchor was lost! Even if they knew of no particular incident, they knew the grounds where the vessels were most likely to anchor and often found it profitable to prospect on the chance that they might find an anchor which had never been reported as lost but had been completely forgotten.

Two vessels were preferred in anchor-dragging. pulling a weighted bight of cable along the bottom on parallel course. The cable had to be strong enough to sustain the weight of any anchor likely to be found, and weighted in such a way that it could slide over rough spots. It also had to be weighted so the dragging arc it described as it slid along would hang up on the exposed fluke of an anchor.

In more modern times and with the adoption of gasoline engines and the power-winches they drive, the system changed. In the days of the bum-boats of Vineyard Haven harbor, such craft as the Maylu, Susie D and lastly the Eben A. Thacher steamed out, probably alone, located anchors, and lifted them aboard by means of their derricks, wire cables and power-winches, saving much exhausting toil.

But while there were anchors on the old dock which would weigh a ton or better, the majority of them weighed much less. The huge sailing vessels of former years had become scarce, and anchors were smaller and lighter. The time came when never a schooner passed, nor yet a tow of barges, either of which would have anchored in the old days, with consequent loss of ground-tackle now and then. Anchor sweeping ended. The collection on the old dock was sold and the dock itself disappeared. Today few men know anything about anchor-dragging. Aside from a couple of small scows there are no locally owned craft capable of lifting a good-sized anchor from the mud. There are few if any anchors to lift, and the effort would pay but little if entered upon.

Compiled by Cynthia Meisner