Low’s first adventure in the brigantine took place on the following Sunday when a sloop belonging to Amboy, in New Jersey, fell into his hands. This vessel he rifled of provisions and then let go. This happened off Block Island near the Rhode Island coast. The same day he captured and plundered a sloop belonging to Newport, commanded by James Cahoon, and took away his mainsail and provisions and water. His bowsprit was cut away and all his rigging and thrown overboard intending thereby to prevent his getting in to give the alarm. Cahoon himself was badly cut in the arm during the scrimmage. Low then stood away to the south-eastward, with all the sail that could be made, there being then but little wind at the time.

He judged well in making haste to get away from the coast for notwithstanding the disabled condition of Cahoon’s sloop she reached Block Island about midnight and a whale boat was sent out at once with the news which reached Newport about seven the next morning. The Governor immediately ordered the drums to be beaten about the town for volunteers to go in search of the pirates and two of the best sloops in the harbor were armed and fitted out. One of these sloops, commanded by Capt. John Headland, mounted ten guns and carried eighty men. The other sloop, which was commanded by Capt. John Brown, jun., was armed with six guns and plenty of small arms and carried sixty men. These sloops were both under sail before sunset, each commander carrying a ten days’ commission from the Governor. At about the same time the pirate vessel could be seen from Block Island. But good fortune favored Low and the sloops returned to Newport several days afterwards without so much as catching sight of the brigantine.

Proclamation also was made in Boston, by beat of drum, for the encouragement of volunteers to engage against the pirates and over a hundred men enlisted under Capt. Peter Papillion who fitted out a ship and sailed shortly; but he, too, returned to harbor without finding Low, but bringing in the brigantine “Rebecca” which Low had turned over to Captain Flucker at Port Roseway, near the southern end of Acadia (Nova Scotia), to carry home the Marblehead fishermen taken by him, he having shipped his arms and stores on board a recently built schooner belonging to Marblehead.

By the Boston News-Letter of July 9, 1722, we learn that sundry goods left by the pirates on board the brigantine “Rebecca” were to be sold at publick vendue at the house of Captain Long in Charlestown. These consisted of “1 Turtle Net, 1 Scarlet Jacket, 1 small Still, 2 pair Steel yards, 1 Jack and Pendant, 2 doz. Plates, 2 papers of Pins, 5 Horn books, 2 pieces of cantaloons, 1 main-sail, Boom and small Cable belonging to a Scooner, a small Boat and 20 yards of old Canvas.” There was also found cast ashore on the back side of Martha’s Vineyard, a sloop supposed to have been taken and set adrift by Low, on board of which were a few shillings in silver money and some strips of paper on which were found written the names of Dan Hide, Nath. Hall and John Wall. This Dan Hide was one of Low’s crew and about a year later he was hanged at Newport, as will be told at length in another place.

After his escape from the attacking expeditions sent out from Newport and Boston, Captain Low went among the islands at the mouth of Buzzard’s Bay, in search of enough fresh water to make the run to the Bahamas. He remained here for some days while his boat crews stole sheep at No Man’s Land and rifled whale boats out of Nantucket. Changing his mind about the course towards the Bahamas, he then sailed northerly towards Marblehead and on the afternoon of Friday, June 15th, put into the harbor of Roseway which is located near the arm of the sea that makes up to what is now Shelburne, Nova Scotia.

At that time it was the habit of the banks fishermen to come into Port Roseway for a Sunday’s rest and when Low sailed into the harbor he found thirteen vessels at anchor. They supposed him to be inward bound from the West Indies and his arrival gave no concern. But soon a boat from the brigantine, with four men, came alongside the fishing vessels, one after another, the men coming aboard as though to make a friendly visit to inquire for news. When on deck the four men drew cutlasses and pistols from under their clothes and cursing and swearing demanded instant surrender. Taken by surprise the fishermen of course submitted and by this means all the vessels in the harbor were captured and afterwards plundered.

Among them was a newly-built schooner, the “Mary,” of eighty tons, owned by Joseph Dolliber of Marblehead, clean and a good sailer. Low liked her lines and decided to appropriate her for his own use, so he renamed her the “Fancy” and the guns, stores and men were transferred from the brigantine. The fishermen from the different vessels were then put on board the brigantine and Captain Flucker was ordered to make sail for Boston. Meanwhile, Low forced a number of likely men from among the fishermen including Philip Ashton, Nicholas Merritt, Joseph Libbie, Lawrence Fabens and two others from Marblehead and four men belonging to the Isle of Shoals.

On Tuesday afternoon, June 19th, 1722, Low and his company sailed from Port Roseway bound for the Newfoundland coast and arrived at the mouth of St. John’s harbor in a fog which lifted somewhat disclosing a ship riding at anchor within the harbor. She looked to Low like a fish-trader and he determined to attempt her capture by a stratagem. All of his men were ordered below, save six or seven, to make a show of being a fisherman, and so he sailed boldly into the harbor intending to run alongside the ship and bring her off. Before having gone far, however, a small fishing boat was met coming out which hailed them asking from what port they had come. Low answered, “from Barbadoes, loaded with rum and sugar”; and then asked the fisherman what large ship that was in the harbor. Imagine his chagrin when they replied that it was the “Solebay,” man-of-war. He immediately put about and escaped before the suspicious fishermen could alarm the town. This happened on July 2d.

At Carbonear, a small harbor about fifteen leagues farther to the north, Low was more successful, for going on shore and meeting little opposition, he plundered the place and burned all the houses. The next day he sailed for the Grand Banks where he took seven or eight vessels including a French banker, a ship of nearly four hundred tons armed with two guns. Considerable rigging and ammunition was secured and a number of fishermen were forced. Late in the month he had an encounter with two sloops from Canso bound for Annapolis-Royal loaded with provisions for the garrison and having soldiers on board. Low’s schooner was the better sailer and coming up began the attack. The red coats at once replied and gave him so warm a reception that Low sheered off and a fog coming on they escaped into Annapolis after having been chased by Low for two days and a night.[106] About the time the French banker was taken, the news came that the “Solebay” was cruising about in search of him so Low decided to steer for the Leeward Islands taking with him the French ship. While on the voyage down they ran into a hurricane that nearly ended matters. The sea ran mountains high and all hands were employed both day and night keeping the pump constantly going besides bailing with buckets and yet finding themselves unable to keep the vessel free. The schooner made somewhat the better weather of it but on board the ship they began to hoist out their heavy goods and provisions and throw them overboard together with six guns in order to lighten the vessel. They even debated cutting away the masts, but the ship making less water, so that they could at last keep it under with the pump, instead of cutting away the masts they were made more secure by means of preventer-shrouds and by laying-to on the larboard tack, the hurricane was safely ridden out. The schooner split her mainsail, sprung her bowsprit and both of her anchors had to be cut away.

After the storm, Low went to a small island, one of the westernmost of the Caribbees, and there refitted his vessels so far as possible with the supplies at hand and traded goods with the natives for provisions. As soon as the ship was ready he then decided to make a short cruise in her leaving the schooner at anchor until their return. They hadn’t been out many days before they came upon a ship that had lost all her masts in the storm. She was a rich find for they plundered her of money and goods amounting to over a thousand pounds in value. This ship was bound home from Barbadoes and was then slowly making her way under jury-rig to Antigua to refit, where she afterwards safely arrived but minus the best of her cargo.