Tory Sailing Activities on the Chesapeake Bay in the 1700s

Joseph Wheland

During the American Revolution, much of the lower shore of the Chesapeake Bay was Tory, and constantly the cause for militia units to be sent to root them out. The marshes and islands around Pocomoke and Tangier Sounds provided places for Loyalist privateers to hide, collect prize vessels, and dissrupt the flow of foods and other essential supplies to the rebellious colonies, as well as sending much of these items to the British. Usually they would seize cargo from other vessels, or raid the dock and stores of plantations, burning the wharf after taking all they could carry. They had various leaders, but one of the most famous is Joseph Wheland, who was wounded once, taken prisoner twice, but was able to talk his way out of jails. He was described once by a captain who managed to escape him as "a tall gaunt-looking fellow in his shirt sleeves, wearing a gold-laced jacket that he had robbed from some trooper on the Eastern Shore." -Captain John Greenwood, 1781

Greenwood also gives us an acount of the men who  were in Wheland's company.

a set of gallows-marked rascals.. there whole object was to plunder and they paid no manner or regard to the vessel they despoiled, be it loyal or otherwise.... Captain Whelan appeared to me to be as great a villian as ever was unhung and all such characters the British seemed to encourage in their employ... -Maryland Historical Magazine

The vessels varied depending on availability, and though these Tories did procure schooners and Barges and work in large groups, usually they used open boats with maybe a four pounder gun, and or several swivel guns mounted fore and aft. They were propelled by sail when wind was available, or often rowed to the plantations they plundered, or up the rivers where they would hide. As a whole, patriot colonials referred to them as "refugee barges" or "Picaroons."

The tools of the trade ranged from rowing galley's and pilot skiffs to schooners, whale boats and barges. Most careers consisted of hiding in river marshes, and from these bases launching raids against civilian homes, skirmishes, and plundering of merchantmen schooners.

Although things started with Lord Dunmore's fleet entering the bay in 1776, when in 1777 Admiral Howe's invasion fleet headed up the bay towards Philadelphia, an uninterrupted period of native privateering began. From then until the end of the war, not only did the large engagements continue on land, but the loyalists of the region waged a guerrilla war against the merchant ships, rich tidal plantations, and the state navies of Maryland and Virginia.

This withdrawal actually worked to force ships headed for the potomac to turn around and head South, towards the picaroons. Wheland continued to seize vessels and supply the fleet, until summoned to return to assist Dunmore in his assent up the potomac for water, but in late July, back in Holland Straits and recovering from mallpox, he was seized by 30 patriots under the command of Major Daniel Fallin.

One of the most famous is Joseph Wheland, Jr. who started his career by first trading with Dunmore's fleet, and then he later joined the King's men, and was in command of a loyalist squadron charged with foraging and raiding on the Eastern Shore. This included two ten gun sloops, an armed schooner, and a pilot boat.

Wheland was sentenced to be confined to a log jail in Frederick County until he made full restitution to John White for the burning of his sloop, and and he paid a bond of good conduct. Three others were seized along with Wheland; Robert Howith, John Price, and Robert Howith, and were sentenced to an Anne ArundelCounty jail and assessed to post bonds of 20 to 50 pounds each. Wheland was imprisoned for five years.

In June of 1776, he invaded Hopkins Island and carried off possibly sixty cattle, two men, and various other items of value, and moved on to Somerset County, raiding only patriot areas, since much of the county was Tory. In many cases, these early raids included personal attack, so that Wheland's men could inflict reprisals upon personal enemies.

From this point until 1779, most of the Tory's acting in the bay were from New York, and usually working only as part of Royal Naval schemes. The Maryland and Virginia navies were effective at keeping things down to low level. Most local picaroons were reduced to smaller operations, closer to their own homes. Ships that ran aground, or were considered fair and easy prey.

These raids resulted initialy in to things. First, the county militias were run ragged as they raced from place to place, usually arriving too late, never knowing where the next attack would occur. Secondly, Loyalist elements in the areas were encouraged to hold open public gatherings, and to work in concert with Dunmore's forces, but by July, Dunmore was forced to retreat to the Potomac River island of St. George, unbeknownst to Wheland.

Although colonial patriots heard only rumors, the raiders knew full well that there was a large group of ships bound from New York for the bay. Captain George Gayton entered the bay, with General Alexander Leslie and 2,500 soldiers. Dolphin and  Plater were the only two ships left to the Maryland State Navy, all the others having been auctioned off.

In 1779, the Maryland Navy schooners Dolphin and        Plater began to cruise the area of Tangier Sound while Colonel Dashiell and the Somerset County Militia coordinated operations on land. The two most important to be searched for, Mister and Carmine, were never found, though Mister was seized later on in Virginia. He probably escaped through their net, and at this time made contact with Admiral Collier.

At the same time,Joseph Dashiell and other militia commanders were running into problems with their defense efforts. Their men refused to accept the revolutionary money as pay, and he could barely maintain a force of 30 men. Tax collectors had collected nothing to add to his funds. Worse yet, the arms lent to Captain Robert Dashiell of the Maryland State Navy by the state had been seized by raiders.

Admiral Sir George Collier burned Portsmouth, plundered Suffolk, and destroyed many ships on the Elizabeth River in 1779. By the summer of 1780, privateers were operating from the potomac to tangier sound. By July, the James was blockaded, and there were an estimated 25 different Tory vessels on the bay, and the picaroons were back in force. Up and down both banks of teh Chesapeake, houses were raided, livestock and slaves stolen. By the fall, These New York Privateers and local Picaroons controlled the bay. In many of the reports that fall, slaves were mentioned as having run away to join the tory forces. These freed slaves gained a reputation for fierceness, and  greatly helped to intimidate white opponents. During this time, places like Dames Quarter and others were so tory that phrases such as "welcomed with open arms" are used to describe how picaroons and privateers were received.

Raiders concentrated first on the Pautxant and Potomac rivers, and then, who should reappear, but Joseph Wheland, JR, released on 10,000 pounds bond, posted by friends. After visiting George Dashiell and convincing him that he was even prepared to build a barge to attack loyalist raiders, and then getting George to write the Governor of Virginia to vindicate him, Wheland turned right around and seized a patriot vessel on August 31, 1780, using only a pilot boat with a jib, and a few select veterans. Dashiell only learned of this by letter after the fact, from Colonel Henry Cooper of Dorchester County.  Wheland was soon back working in concert with the British fleet.

In 1781, Benedict Arnold captured not only Richmond and Petersburg, but in doing so destroyed the majority of the Virginian State Navy. The islands of Tangier sound were becoming a well build base of operations for the raiders, who continued to plunder Worchester and Somerset counties. Raiders were beginning to carry out full scale invasions of towns like Vienna, complete with bombardments and an organized invasion, demanding only grain (at a fair market price) and promising to leave grain for the inhabitants, and not to plunder further, as part of their collection of supplies for Arnold's forces in Virginia. The inhabitants agreed, and the raiders honored their word.

While some raiders were organized and efficient, others were simply brutal. Captain John McMullen actually dragged Captain Gale of the Somerset Militia from his bed, carried him to Clay Island,  whipped and hung him. Gale survived, though McMullen wanted to drown him, but the crew convinced him otherwise, and he was released after swearing to never raise arms against the King again.

Wheland resurfaced in July of 1782. On the 5th, the Brig Ranger was on her way out from Alexandria, Virginia, when she was set upon by two picaroons at 1:00 in the morning. Captain Thomas Simmons was not aware of them until they were too close for cannon to be effective, and so they repelled borders with pikes for some time, and then "played them with cold shot" until they finally forced the picaroons to withdraw. Wheland, commanding one of the picaroons, had been wounded while his counterpart, Captain Barry, had been killed.

With Annapolis blockaded, the British moved North, landing at Poole's Island and various points in Harford County. Again the  Potomac and Patuxent were raided, moving as high as Lower Marlboro. Local towns began to form their own defensive navies, building and arming their own vessels. Wheland was moving almost unhindered along the eastern shore,  preferring the company of his lieutenant, William Timmons, and a small whaleboat, to his larger barge. By Summer, Wheland and his cohorts were raiding indiscriminately from the merchants and farmers on both sides of the war, to the shock of the leaders of both sides, but they had more  important things to deal with,and left this problem to the individual colonies themselves.

Meanwhile, the good people of Pocomoke had convinced Maryland to assist them in building the Protector, a barge armed with a 24  pounder, and a full compliment of 100 men. In Annapolis, the Decoy and the Plater were dispatched along with another boat, under the command of Captain Alexander Trueman, to pursue another Tory vessel that had taken to the West River. Eventually, picaroons were reported in the strength of 4 privateers and four barges blocking the Pocomoke Sound alone, with others operating elsewhere, up and down the bay.

Even a this point, Washington himself was of the opinion that "the colonies would have to rid themselves of the picaroon," since French vessels could not pursue up the rivers as far as these small raider vessels could travel, and the French themselves were busy with the Tory raiders of the Capes. On the 8th, Wheland and his lieutenant, Timmons, were sighted as part of a party that seized the schooner Greyhound near Devil's Island (Deal Island). A passenger on the Greyhound, a Mr. Funeral, also witnessed the successful seizure of several other bay craft, while he was Wheland's prisoner.

The surender of Cornwallis at Yorktown October 19, 1781, left the Chesapeake under the relative safety of our french allies patrols. Wheland retreated, but, news came from North Carolina that he and his lieutenant had been captured, and though Maryland authorities offered to send and collect these men, no reply from North Carolina is recorded, and Wheland and Timmons had escaped. In 1782, they were back to  plundering.

The Battle of Kedge's Straits (Cager's Straits)

The Worchester County Militia was called out, to little effect. Captain Zedekiah Walley was ordered to take command the barges constructed in Baltimore and to join with the French fleet in July, but due to lack of funds to hire or pay crews, the barges were still in Baltimore in September. He finally was able to set out, and returned with four American vessels, recaptured from other picaroons working the bay.

In November, now Commodore Walley, he made contact once again and started to clear out Gwynn's Island, Cape Charles, and Smith's Island, seizing one vessel and driving the others out of the bay completely, to the open sea. One man seized at this point was Peter Francks, a Portugee, "who is notoriously known "to be at and privy to almost every house burnt on the Eastern Shore."

Walley learned that the enemy barges were laying in wait for him after a rendezvous at Chincoteague Bay (on the ocean side of the Eastern Shore), but he felt his duty was only to keep them out of the Bay itself. Learning that the flotilla was again in the bay, he moved his small group from Onancock, Virginia to Tangier Island, where the Tory group was last seen.

Arriving near Tangier, Captain Frazier was dispatched to the island for information with the Defense. After raising the British colors, Captain Frazier approached the Island, which was wholly Tory. The trick worked, and he learned from a local that six picaroon barges had left his house for Fox Island (off Pocomoke Sound), headed for a night at Cager's (Kedge's) Straits (between Smith and South Marsh islands).

At Fox Island, Second Lieutenant Samuel Handy was sent to the island for information, aboard the Languedoc, where he learned that the enemy were again headed north. They decided to sail for Kedge's Straits and lay in wait.  They anchored at 4:00am.

At 6:00am, the enemy was sighted sailing the Straits, and moving closer by 8:00am, the enemy took in sail, formed line, and rowed towards the American ships. At 200 yards they raised their colors and approached Captain Frazier, bow on. Frazier also took in sail and raised his colors.

Soon all ships were engaged, and although brisk fire was maintained on both sides, eventually, a fire broke out aboard Commodore Walley's barge, the Protector, due to a spilled cartridge on the deck. Soon afterward, a second fire broke out and many of the men jumped overboard. Two picaroon barges pulled along side to board her, one of them being the Kidnapper. It was reported initially by Dashiell to the Governor later that all the crew were killed in the boarding and thrown overboard, except for the bodies of Commodore Walley and Lieutenant Handy. Since there were reports from other members of the crew, this is rather false. In reality over 20 crewmen were lost.

The truth was that in fact, Captain Dashiell retreated without firing a shot, and was later discharged from service. The Languedoc, and the Flying Fish retreated as well. The other three enemy vessels attacked Frasier's vessel, who  was then forced to retreat. By 4:00pm, the enemy gave up their pursuit, and turned away.

The final result of this Maryland Colonial Navy Failure was that Frazier found himself commander of the barges, but Somerset and Dorchester counties were left open to further attacks because Governor Pacca was unable to convince the crews to re-enlist or volunteer for service, and was forced to let them go. Only afterward was it learned that it was Wheland who was in sole command of the Refugee Boats.

Wheland built winter quarters on Tangier Island and in February The British Loyalist "Pirates" resumed their work soon after. The Governor was still facing last years barge bills, and appeals to the merchants of Maryland for assistance with these debts met with little success. Wheland, meanwhile, had attacked and sacked the town of Benedict, thirty miles up the Pautuxent River. He had also dispatched a second group that operated as far north as Kent Point.

By March 22, Captain John Lynn (of the colonial army) was waiting for barges to arrive for his use in an attempt finally to find Wheland, when peace was declared on the 29th. In one book, an assault on Tangier Island is claimed, but since there are no sources listed to support this claim (we are still researching this), and since it would have occurred after peace was declared, this is doubtful, even with the slow communications of the period.

The Elusive, resourceful Captain Joseph Wheland's days after the war? No one knows for sure where he finally ended up. One report is that he was killed in that supposed raid on the Tangier camp, which probably never happened. There was a report that his Galley was captured near Ocracoke, North Carolina, but no report exists as to what happened to her commander. The watermen of the eastern shore claim he went        back to hiding in the marshes of Dorchester County after the war, went mad, and his screams and groans could be heard frequently in the marsh from great distances away. (a lovely tale to frighten the children if they don't behave)

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