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."
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.
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        smallpox, 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 Arundel        County 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.
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.
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        Platerwere the only two ships left        to the Maryland State Navy, all the others having been auctioned        off.
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.
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.
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        sale 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 beencaptured, and though Maryland authorities offered        to send and collect these men, no reply from North Carolina is recorded,        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 with,        if they don't behave, eh?)
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