After de Grasse left the Chesapeake, its naval defense reverted once more to the Maryland and Virginia navies. The continued war would not go well for the Chesapeake planters who supported the state navies. Seven months after the Battle of the Saints, another naval confrontation would take place which would justify the confidence British officers and ministers had put in the commitment of Loyalists.
Before the war, many landless and poor Chesapeake farmers could not make a living from the traditional agricultural staples of tobacco and wheat. They became refugees by gravitating to the coastal marshes, then to the adjacent islands and finally to islands distant from the mainland. Here their only need was a canoe to allow them to navigate the water. The abundance of shellfish, fish and wild fowl, along with a patch of corn, sustained them and their families. Most of these islands and marshland farmers failed to develop plantation agriculture and thus they were outside of the great planter’s economy and influence. Instead, these marginal lands would become the home of an independent breed of watermen who would contribute to the Loyalist insurrection that had been going on. The most famous of them was Joseph Whaland Jr.
Early in the war, as a Loyalist, Whaland had been taken from the Chesapeake’s Eastern Shore and imprisoned in Frederick and Baltimore, Maryland. He finally returned to the Eastern Shore in mid-1780, when his galley was once more recognized on the Chesapeake. He was elated by the appearance of Leslie and Gayton in October 1780. He had been discharged on a bond, in which his bondsmen, Samuel Covington and Thomas Holbrook, acknowledged themselves to be indebted to the State of Maryland for £5–10,000 each, if Whaland failed to appear before Governor Thomas Sim Lee and his Council ‘to answer a charge of high treason’.1 His bond was presumably forfeited.
Before his confinement, the Eastern Shore’s Smith Island had been Whaland’s earliest center of operations, from where in 1776 he had cooperated with Virginia’s Governor Dunmore. The ‘tall, slim, gallows looking’ waterman had used the island as a base from which to recruit ships to join Dunmore.2 In league with Smith Island’s inhabitants, Whaland was able to bring in prizes, distribute their cargos on the island, refit ships and form crews from the mixed population. In late June, working with Dunmore’s tenders, he participated in a Hopkins Island raid, taking sixty head of cattle, two young men, and ‘everything else that was valuable’. Later, the Accomack County Committee described Whaland as one who ‘was then bound to the Kings fleet with 20 or 30 people of his own stamp’.
While Whaland joined the Dunmore–Hamond fleet, he did not stay for long. Smallpox was raging in the ships and he and some of his crew caught it. By chance at Hooper Straits in July 1776, thirty Dorchester militia under Major Daniel Fallin found him among his Smith Island crew recuperating from smallpox. The rebels were able to easily take his schooner.3 Brought before the Dorchester County Committee of Observation, his previous activities were revealed. For these offenses the Committee sent Whaland across the bay for safe-keeping to the distant Frederick County jail.
Now out of confinement, Whaland was seen in a pilot boat near Popular Island, Maryland.4 From Holland and Tangier Islands a majority of his crews were blacks or mulattoes, probably runaway slaves. They had mariner backgrounds, were refugees on the islands and had become watermen. They had continued operating while Whaland was imprisoned.
Upon his return, Whaland superficially appeared willing to put aside his Loyalism. In December 1780, he met with Somerset County Lieutenant George Dashiell and sought to explain away his former treasonous actions.5 His involvement in attacking rebel shipping, he claimed, was actually forced as he had been a captive in irons, locked up below decks during the actual raiding. Now he wanted to come up the Wicomico River with his family, removing them from possible Loyalist raiders. To prove his newfound change of heart, he told Dashiell he would contribute to the expense of building a barge to be used against Loyalists. Dashiell was completely taken in by his story and sent a letter to Governor Lee expressing his belief in Whaland’s sincerity.
Immediately afterward, however, Dashiell received an express letter from Colonel Henry Hooper of Dorchester, requesting that he arrest Whaland, enclosing an affidavit from Captain Valentine Peyton of Stafford County, Virginia.6 Peyton had been captured by Whaland in August off Poplar Island. Whaland had returned to his former activities without batting an eyelid, in command of a pilot barge fitted with a jib and a crew of veteran Loyalists. Soon, Captain Oakley Haddaway’s vessel was also taken, as was one belonging to William Barnes. Seeking revenge, Haddaway would become a first lieutenant on Robert Dashiell’s barge Terrible, and Barnes would have the same rank on Levin Spedden’s Revenge, Maryland navy vessels.
By February 1781, Whaland was in command of four barges that raided Benedict on the Patuxent River, Virginia. As Whaland reappeared, from Cambridge in Dorchester, Captain John Smoot wrote that rebel transports had been seized with supplies destined for the Continental army and sent to the British. His own tobacco-loaded vessels had been taken, so in retaliation he wanted the raiders hanged and their homes burned.7 Soon after, a letter sent from Salisbury to Governor Lee reported:
From every appearance we are in much worse situation than we have been in this war. A great majority of our people seem determined to give over [to the British] … It is with great difficulty we can keep a guard of thirty men together and many have refused expressly to march against the enemy. I am sorry to inform that very few people will take a shilling of the new [state paper] money.8
In March, petitioners sent a request to the state council to defend ‘those who live contiguous to navigation’ in Somerset County.9 George Dashiell’s brother, Joseph, at first unaware of Whaland’s release, was more than a little upset over his reappearance. Dashiell complained to Governor Lee that Whaland should not have been released:
Joseph [Whaland] that old offender was down in Somerset plundering again and we have reason to believe that the Gaoler in Baltimore is alone to blame … If this practice is followed no one will venture to take any of them up and send them forward as they will be there to suffer for it. If I had directions to go into Somerset, I think I could apprehend him, as he has lately robed a certain Thomas Reuker who I think would assist me to trap him.10
In the Chesapeake’s narrow waters, the barge had replaced the galley because while slower, its flat bottom provided more stability for heavy caliber artillery. Whaland had worked with the Royal Navy’s armed barges, tenders and Loyalist privateers, learning secret signals of recognition: three successive hoistings and lowerings of the mainsail, and then an English jack raised at the masthead. In June, his barge Resolution and four others invaded the Shore’s Wicomico and Pocomoke Rivers.11 While he commanded the Resolution, the other barges were under his trusted lieutenants: Shadrack Horsman, Jonathan Robinson, and the brothers Michael and William Timmons Jr. of Hooper’s Straits. Up the Wicomico they plundered widow Elsey and Captain Elijah Evans at the lower ferry in Worcester and then gathered at Courtney Island.
By mid-July 1781, wealthy Somerset militia Captain Henry Gale – a descendant of George Gale of Whitehaven – was hauled from his bed in his Whitehaven, Maryland home by Whaland’s protégé, Captain John McMullen. He was commander of the barge Restoration, leading a band of four white and nine black watermen. Gale’s house was ransacked and he was hauled off to Sandy Island at the mouth of the Nanticoke River, where he was accused of having participated in the court martial that had sentenced Loyalist Marmaduke Mister to death. They tied Gale to a post ‘where he was most inhumanly whipt six lashes’ and then hung by a rope around his neck from a tree, until they believed him dead.12 Soon after, he was cut down and revived by Loyalist John Timmons. McMullen attempted to persuade his crew to hang their victim again, but they refused. McMullen proposed drowning Gale, but again they refused. Later, Gale wrote a letter to Governor Lee asking for a reprieve of Timmons for his brave act of mercy.
After Whaland’s return, the Timmons brothers of Hooper’s Strait – John, Michael and William – served as officers of his crew.13 William commanded a barge. William and Michael were with him in the 1781 raid of the Wicomico River, and when Whaland left Chesapeake Bay in a British squadron, Michael accompanied him to North Carolina. Whaland, John McMullen and Jonathan Robinson frequently acted in concert, occasionally gathering at Courtney’s Island before setting out upon a cruise. They often employed black slaves as crewmen, whom they freed during their attacks. McMullen would be captured in July 1781 by Commodore Grason’s fleet.
While Yorktown was besieged by the allies, Whaland’s Rover and a smaller galley captained by a ‘mulatoo, named George, six feet high’ captured Captain John Greenwood’s schooner, placed a prize crew on it commanded by George, and made Greenwood and his crew prisoners.14 The Rover then removed a cargo Greenwood had left at Gwynn’s warehouse, including a hogshead of rum. Enraged Greenwood described watermen as:
A set of gallows-marked rascals, fit for nothing but thieves; hellbounds and plunderers from inoffensive, unarmed people, they seemed to be without any kind of principle and I really believe that ten honest, religious, determined men could intimidate or drive a hundred such villains.15
Despite Greenwood’s views, many in Whaland’s crews came from respectable local middling families, although the war forced them to become refugees and earn a living as watermen. Whaland himself had lived on Garden Island, Straights Hundred, Dorchester.16 He held 500 acres, a lot in Norfolk, an interest in several vessels and was a recognized pilot. His father, Joseph Sr., was a Dorchester planter, and his brother, Thomas, jointly owned a schooner with him. In 1777, Joseph Sr. and Thomas turned the tables on Major Daniel Fallin by protesting the seizure a year earlier of their vessel by his militia, appealing in writing to the Committee of Safety for the return of their vessel. Fallin had claimed the boat belonged to Joseph Jr., who had been detained because it was allegedly in the service of the enemy. On the contrary, Joseph Sr. claimed it was not his son’s vessel, who at the time was respectably employed as a mariner on the Potomac River by William Geahagan, a Somerset merchant. This was an untruth; in reality, Whaland was trading with Governor Dunmore at Gwynn’s Island, but it showed how the family protected its own.
Tangier Island off Pocomoke Sound had been patented in the early eighteenth century by Virginia planter families, but no evidence of settlement exists and it is assumed it was used to graze cattle.17 Thus Tangier was not settled until the Revolution, populated chiefly by white and black Loyalist refugees, most of them watermen. Its combination of difficult access and yet a strategic location at the mouths of several Eastern Shore rivers, not far from the Norfolk–Portsmouth area, made it an ideal location for these refugees.
Early in 1781, Joseph Dashiell was distraught over the nest of Loyalists found on Tangier Sound. Citing the recent robbery of Planner Williams, by a band of nine island watermen, whom he suspected operated ‘under the color of belonging to the British cruisers’,18 Dashiell offered help to Governor Lee ‘that whenever your excellency & council propose to remove the people and stock of the islands [of Tangier Sound] I should be glad to assist with all my heart as I consider them at this time the most dangerous enemy we have to watch the motions of …’
A year later, the British flag still flew over Tangier Island. In reaction, the state governments aimed ‘to depopulate the Tangier Islands’. In April, the Maryland Council ordered Commodore Thomas Grason to remove the inhabitants, including the old men, women and children.19 Here was a threat that would motivate the islanders to defend themselves.
Thomas Grason was a worthy opponent for Whaland. In March 1779, with a squadron of Maryland galleys and tenders, he had first cruised off Cape Charles to protect rebel ships. Three months later, in the same waters, with the sloop Hannah and the galleys Conqueror and Chester, he opposed a mysterious British ship, but it easily outdistanced his squadron.20 After this encounter, the fleet was not sent out again, for the state was beginning to dispose of its navy.
A native of Talbot County, Grason had inherited the plantation, Grason’s Discovery, from his father Richard. He was also an experienced sailor. In 1761, at the age of 27, he had served in a Royal Navy frigate off the coast of France.21 By 1773, he was master of HMS Somerset and he deeded his Talbot land to his brother Richard, a sign of his inability to pay attention to it. However, five years later we find him commodore of the Maryland navy in command of the Dolphin.
By July 1781, the Maryland navy was revived and Grason again cruised, commanding the Revenge, supported by captains Robert Dashiell’s and Levin Spedden’s ships, a bateau and two smaller vessels. They took the Loyalist barge Restoration and two tenders, while a second barge and bateau escaped. ‘The event has given general joy,’ wrote planter Matthew Tilghman, ‘And if we cannot flatter ourselves with peace, we begin to think we have a chance of remaining safe from the plunderers that have late infested us.’22 The captured Loyalist vessels were displayed at Haddaway’s Ferry to demonstrate that the bay could be secure. Tilghman boasted the rebel barges would attack any vessel, except a British fleet. Months later, Grason commanded several vessels transporting part of Washington’s army from the Head of Elk to Virginia, and provided provisions for the army besieging Yorktown.
In April 1782, Grason was ordered to the Miles River in Talbot County to supervise the outfitting of four barges, enlist seamen and marines and, as noted, expel the inhabitants of Tangier Islands.23 He commanded the Revenge, and with him were the Intrepid, Terrible and tender Planter. Grason’s squadron was a family affair as son George was his second lieutenant on the Revenge, while the tender Nancy was commanded by Thomas Grason Jr., and Richard Grason served as second lieutenant on the Terrible.
On May 10, when Grason approached Janes Island with his flagship barge the Revenge and three other vessels, he was confronted by three to five Loyalist barges. In the battle that followed, the Revenge was taken and Robert Dashiell’s barge Terrible was blown up. In the words of James Bryant, a seaman on the Terrible, ‘most parts of the crew was lost’.24 Grason and several of his men were killed, ending his naval career at age of 49. The Loyalist barges took the survivors prisoner, including his son George. Whaland had returned from imprisonment in North Carolina, but it is not evident that he was involved in this action. Grason’s defeat showed that the islanders did not take threats to their existence lightly.
Raids by Loyalist watermen were now unopposed and even rebel privateers feared them. In July, two Loyalist barges under John Anderson attacked the Massachusetts privateer Ranger off St George’s Island. After three hours of fighting, the ships disengaged to care for their wounded. Three days later, Loyalist barges seized the privateer schooner Greyhound in Hooper Straits, a ‘boat laden with Salt, Peas, Pork, Bacon and some Dry Goods’.25 The captain and his crew were detained for twenty-four hours aboard Whaland’s barge, during which time a passenger, Mr Furnival, claimed he was robbed of his money and watch. The captain and his crew were set ashore at the Loyalist enclave of Dames Quarter. Before he was released, Furnival later reported that he ‘saw several other Bay craft fall into the Fangs of the same Vultures’. On Smith Island, Loyalist watermen attacked George Pruitt’s house and burnt it to the ground, so that he was financially ruined; it was said he took to drinking for the rest of his life.
Against this background, the Chesapeake’s last great naval confrontation came in late November 1782, more than a year after Cornwallis’ surrender at Yorktown. The battle involved armed barges, in which five from the Maryland navy, plus a tender from the Virginia navy, sought to take on six Loyalist barges in the straits north of Tangier Island.26
Commodore Zedekiah Walley, a native of Worcester County and merchant captain trading in the British Isles before the war, now commanded the Maryland squadron of five sail- and oar-driven barges. He was given full authority to command, so long as ‘your operations are not to be extended beyond the Capes of this Bay’.27 The Assembly had diverted funds from the recruitment of its Continental army quota, in order to build four barges for defense of the bay. As noted, the largest and most heavily armed of these ships, Walley’s Protector, was constructed under his direction at Snow Hill. It needed a crew of sixty to service the 24- and 18-pound guns, and required a captain in charge of its marine company. The barge had been financed and built by Somerset County gentlemen and donated to the Maryland navy. Robert Dashiell, a cousin of George and Joseph, represented the family in Walley’s squadron, commanding the new barge, Terrible.
Walley had been Grason’s second in command, and Maryland’s Governor Thomas Johnson ordered him to take up where Grason had left off and destroy the bay’s watermen Loyalists. His foray began auspiciously, as he was able to chase Loyalist barges from Gwynn’s Island southward toward Cape Charles.28 In mid-November near Smith Island, his fleet caught the slowest Loyalist privateer Jolly Tar, commanded by Captain Daniel Brooks of Somerset. In the crew were five blacks and several leading Loyalists, Jacob Extine, Samuel Outten and Peter Franks, a Portuguese, known for his raiding exploits. Outten had previously served as captain of the privateer barge Trimmer. After his capture, he was paroled and restricted to Annapolis by the Maryland Council. He was allowed, however, to return home, visiting friends and passing through the site of his exploits on his way to see them.
Finding the Loyalist navy too strong for his lightly manned barges, Walley took his squadron, including the Jolly Tar, into Virginia’s Onancock Creek to get reinforcements. At the port of Onancock, he found a barge and asked Onancock citizens to fit and man it. On November 28, Colonel John Cropper received a letter from Walley explaining his proposed attack on Whaland’s barges, then in the bay off Onancock Creek, and asking for volunteers from Accomack to serve in his fleet as marines.29 Cropper gathered twenty-five to fifty local men, who went on the Onancock barge, although it turned out to be unseaworthy and was forced to return. Most were then transferred to the Virginia tender Flying Fish, but Cropper and nine ‘gentlemen’ boarded Walley’s flagship, Protector. All told, Walley’s squadron now consisted of four barges, a galley and the captured sloop Jolly Tar, now renamed Languedoc.
Joseph Whaland Jr. had established a rendezvous for his barges at Hog Island in the Hooper Straits, a place where their plunder could be disposed of. His squadron consisted of five barge-rigged vessels, one of which was a galley. His flagship was the Kidnapper. His known captains were Fling of the Victory, Young of the Ranger, William Perrey of the Peryorge and Nathan Adams of the Ladies Revenge.30 From there he moved north by Tangier Island and then into Tangier Sound and finally westward under easy sail to Kedges Straits, where to the north the water divides Smith Island from South Marsh Island.
Walley’s squadron anchored off Janes Island, the site of Grason’s defeat only seven months earlier, and then followed Whaland. On the morning of November 30, Walley pushed the Protector to the head of Kedges Straits, so that it soon outdistanced the rest of his squadron. Whaland spied the Protector and he directed his entire squadron to drop their sails and row in a line toward the Protector. When they were within 200 yards, Whaland’s squadron opened with a unified cannonade.31 The Protector was now joined by the Defence and the Fearnaught, but the latter at the first salvo shattered its bow gun and thereafter had only swivels. As the firing continued, one of the Protector’s gunners broke a cartridge, spilling powder on the deck and in the succeeding cannon shots a flashback occurred, igniting the powder and stacked ammunition chests. These exploded, burning three or four crew members to death, the rest, including the gentlemen, being forced to leap overboard. This was followed by a second explosion of ammunition chests, encouraging the Loyalist barges to advance.
Captain Whaland, in the Kidnapper with two other Loyalist barges, surrounded the Protector, while the other Loyalist barges continued to fire. According to Cropper, ‘There was one continual shower of musket balls, boarding pikes, cutlasses, cold shot and iron stantials for eight or ten minutes, till greatly overpowered by numbers, and having all the officers killed and wounded, we struck to them.’32 Captain Levin Handy, of a wealthy plantation family, commanded the marines aboard the flagship, and believed the casualties so devastating that he attempted to strike its flag, but Walley prevented him. Subordinate Captain Joseph Handy fought on, despite losing an arm, from which injury he died. Cropper had at least four wounds on his body and was rescued by two Loyalists: an Irishman and a former slave of his father’s. Walley was killed and twenty-five crew members were killed or drowned, while twenty-nine were wounded, only eleven being able to save themselves by leaping in the water. Whaland’s vessel had eight killed and eight wounded out of a crew of forty-three blacks and whites. In a bloody ten minutes the Protector belonged to Whaland.
Meanwhile, the other four Maryland barges, including the Defence and Fearnaught, and the Virginia tender, after maneuvering with their oars, turned tail and ran as the Protector was seen to be on fire. In fact, the rebel fleet had never formed a unified line of battle. Some would be pursued by Loyalist barges for nearly 30 miles, as they attempted to hide in the Annemessex or the mouth of the Choptank River, and all ultimately escaped. The flight of most of the Maryland barges led Governor William Paca to initiate an inquiry into the conduct of the other four captains. Cropper blamed the defeat on the ‘dastardly conduct of our comrades’.33 He, Levin Handy and George Dashiell were highly critical of the conduct of Walley’s subordinates. After investigation, captains Levin Spedden of the Fearnaught and Solomon Frazier of the Defence were absolved and reinstated in the Maryland navy. Captains Robert Dashiell, of the Terrible, and Botfield were charged with ‘highly unbecoming and improper conduct’, and suspended. Botfield got off, but for his conduct, Robert Dashiell was cashiered from the Maryland navy, a blot on the family’s reputation. Dashiell was clearly a better shipbuilder than a naval officer. The bloody battle had left wounds in the prestige of the Eastern Shore’s leading families.
Whaland dictated terms to Cropper and he agreed to take the Loyalist wounded to Onancock to have them attended at the public expense, upon condition that Whaland would parole all of his prisoners, both unhurt and wounded.34 The agreement required approval by the Virginia governor in Council and the Assembly. The Kidnapper took the wounded of both sides to Onancock, where they were treated. Whaland’s barges also took forty prisoners and he insisted that the crew of the captured Jolly Tar be released to Hog Island. By December 3, Cropper was back in Onancock to recover, although he was not free until almost two months later when he was exchanged for Samuel Outten of the Jolly Tar’s crew. It took longer for others to be exchanged. Cropper’s honoring of this agreement would cause him financial difficulty.
George Corbin, the Accomack County Lieutenant, arranged the funeral of Walley in Onancock. His body was carried around the square and through the streets by a procession of Accomack County militiamen. He was buried on December 3, 1782, probably in the Corbin family cemetery by Scott Hall, although this burial place may not have been established until later.35 The Maryland and Virginia navies were defeated, a victim of Loyalist barges in the bloodiest confrontation on the Chesapeake’s Eastern Shore, a situation that continued to inspire Loyalism.
In early December, the defense of the bay was now limited to militia. According to Maryland Governor William Paca, the enemy now had thirteen barges, one sloop and two schooners in the bay. Worcester’s Colonel Henry Dennis observed that the Loyalists had created a situation that was ‘truly distressing, for the enemy are now able to continue their depredations in any part of [Worcester or Somerset Counties], and … there is neither arms nor ammunition were the militia disposed to make use of them …’36
Paca’s first hope for assistance was the three ships of the French squadron commanded by Jacques-Aime, Le Saige de la Villesbrunne, left by de Grasse, but they were no longer present. In February 1783, Paca wrote Washington desperately hoping that preliminary peace negotiations would put an immediate end to the watermen’s activities, but the response was not encouraging.37 On March 24, Congress directed Robert Morris to revoke the commissions of all American armed vessels and authorized an approach to Carleton and Digby in New York to cease hostilities. However, they had no instructions from London and refused to respond so that their ships continued to operate at war. Anyone who thinks the war in the Chesapeake ended with the siege of Yorktown should note the situation faced by Paca and Washington in 1783.
Paca was left to refit his remaining barges, but during the winter, crews refused to re-enlist or volunteer. He was promised a 14-gun brig from the French, the Pole Cat, which was to be sent to the Eastern Shore, but no money existed in the treasury to outfit it. He was forced to appeal, as had been done in the past, to Baltimore merchants to raise ships, claiming ‘there is no force belonging to the government able to oppose [the watermen]. Were our barges completely armed and fitted, they would be quite insufficient to the purpose …’38 However, the merchants replied with conditions that he could not meet.
Without the Pole Cat, Paca was able to put together a schooner and two barges under command Captain John Lynn, a soldier in charge of the marines, lacking naval experience. He was to sail to ‘[Deal] Island, one of the upper Tangier Islands, the Place of [Whaland’s] Rendezvous, where they have collected their Plunder, and … they have become so confident by Success, that they think any Precaution for their Security, unnecessary.’39 It was hoped that the number of prizes taken and sent to New York had weakened their force considerably.
To offset Lynn’s inexperience, the exonerated Captain Frazier was asked to go with him. Lynn was warned that if a confrontation appeared he should defer to Frazier’s barge ‘as he is a man of sense …’ in naval matters.40 Remembering the Protector’s fate, Frazier was also advised to watch his ammunition chests. The explosions on the Protector, and earlier on Dashiell’s Terrible at Janes Island, were the result of inexperience, where too much powder was massed on a barge’s single deck. On Royal Navy ships, powder was kept below and brought up by boys in sparkproof containers in small amounts, only enough to fire a gun. Paca’s expedition, however, never got underway as the crew members of the Frazier’s Defence were charged with disobedience and court-martialed, making it impossible to embark.
Meanwhile, Whaland established winter quarters for his five barges and sloop on Tangier and Hog Islands. In February 1783, he commanded them as they landed at Benedict on the Patuxent River, Maryland and raided Philip Ferguson’s farm, taking 12,000 pounds of salt pork. It was reported that when asked who led the raiders, he scrolled his signature with a piece of red chalk: ‘Joseph Whaland, Commander of the Sloop Rover’.41
Peace between Britain and the United States was not signed until September 3, 1783 and official recognition of it did not reach America until 1784.42 That year, both the Maryland and Virginia navies were eliminated, making it impossible for further naval action against Whaland and his watermen. With peace, Whaland remained at large. Watermen claimed that he had retired to the marshes of Dorchester County. Apparently, this is where he spent the last years of his life.