Background
By May 1776, Lord Dunmore was in real trouble. After his defeat in the Battle of Great Bridge (December 9, 1775) by Patriot forces, he retreated to Norfolk. But he lacked sufficient forces to hold the city and, along with hundreds of Loyalist citizens, took refuge on British warships and civilian vessels in Norfolk Harbor. After Norfolk was destroyed by fire in January 1776, Dunmore landed his force across the Elizabeth River in Portsmouth. He built defensive earthworks on Tucker’s Point (the present-day site of Norfolk Naval Hospital), which gave him space to disembark the soldiers and Loyalist civilians from the 100 or more vessels collected in the harbor. Dunmore then armed many of these ships in his effort to create a royal Virginia Navy, all while anchored under the protection of Royal Navy warships.
From February through May 1776, the Patriot forces improved their defensive positions surrounding Tucker’s Point and began to mount cannon to fire on Dunmore’s ships. Through spies, Dunmore learned of Patriot plans to board his vessels and burn them. Just when it appeared the Patriots were poised to attack, the HMS Roebuck arrived under Captain Andrew Snape Hammond, a seasoned veteran who immediately recognized the danger Dunmore faced. Within three days, Dunmore had destroyed his barracks and unseaworthy vessels and loaded all soldiers and civilians on serviceable ships. Hammond took command of the convoy and safely moved nearly 100 vessels, including the British warships HMS Roebuck, HMS Fowey, and HMS Otter, to anchorages in Hampton Roads and then sailed north into the Chesapeake Bay and to the waters surrounding Gwynn’s Island, a 2,200-acre island in Gloucester County (present-day Mathews County). The island possessed fresh water, plenty of livestock, and an abundance of fish in the surrounding waters, all of which had been in short supply at Tucker’s Point. The island had one weakness: at one point, it lay only 200 yards from the Virginia mainland. This required a capable warship and several tenders to stand ready twenty-four hours a day to prevent a surprise crossing of the channel by Patriot forces.
Both the Patriots and Dunmore’s forces began preparing battery positions on the narrowest portion of the channel. Dunmore’s force had another significant weakness: disease. Smallpox had ravaged his tightly packed force during his occupation of Tucker’s Point. Another unnamed disease, possibly typhus, also thinned his ranks. Both followed him to Gwynn’s Island, where mortality rates reached six or more individuals per day and reduced his combat force to less than 200 men. His contingent of the 14th Regiment of Foot, the backbone of his land force, numbered only 100 when all were healthy. His white and Black Loyalists could only field another 100 men healthy enough for duty when the forces landed on May 27. Hammond sent marines ashore to supplement the small number of land forces and assist in preparing the defenses. Patriot estimates of 500 defenders on the island, as reported in the Virginia Gazette, were greatly exaggerated.
The Patriots had the manpower, but assembling the force took some time. The 7th Virginia Regiment was the first to arrive and exchanged fire with the tenders in Milford Haven, the bay separating the island from the mainland, as Dunmore’s troops landed on Gwynn’s Island. Local Gloucester County minute companies assisted. Eventually, six companies of the 2nd Minute Battalion, along with several companies of the 2nd and 6th Virginia regiments, joined the 7th to form a two-regiment brigade of about 2,000 soldiers positioned opposite Gwynn’s Island. Other forces were stationed nearby in Jamestown, Burwell’s Ferry, Hampton, Gloucester Town, and Yorktown. Patriot leaders understood that mobile British naval forces could move quickly and occupy or raid unprotected locations at will, necessitating a robust defense in multiple locations.
Sporadic gunfire was exchanged over the next month as the Patriots built earthworks to house cannon and support infantry. Dunmore’s naval forces were active throughout the Chesapeake Bay. They sent small landing parties ashore at unguarded locations, foraged for supplies, including livestock, and transported several hundred Loyalists from the Eastern Shore to join Dunmore. Dunmore also formed a small, mounted unit from the horses available on the island, which he placed under the command of Loyalist John Grymes, one of the island’s leading residents.
The Patriots prepared two battery positions. The upper battery contained two eighteen-pound cannon, and the lower battery, nearer the water, held two nine-pound and three six-pound cannon. This would prove critical to the outcome of the battle.
The Battle of Gwynn’s Island
On the morning of July 9, General Lewis, the senior military officer in Virginia, along with several of his colonels, arrived to inspect the newly completed battery. Lewis could not believe what he saw. Directly in front of the eighteen-pound cannon of the upper battery, less than 500 yards away, was Dunmore’s flagship, the Dunmore, at anchor. The Otter, a more capable warship, had changed places with the Dunmore the previous day so that its hull could be scraped to remove sea growth. Foliage must have obscured the upper battery from view by Dunmore’s forces. The Dunmore, a converted merchant vessel, mounted only six-, four-, and three-pound cannon and had a small crew of about thirty men, mostly Loyalist volunteers, with minimal training in gunnery. Although the Patriot infantry had not assembled the vessels needed to cross over to the island, the target was just too inviting to pass up. Lewis knew Dunmore well, having fought with him at the Battle of Point Pleasant during Lord Dunmore’s War. Dunmore was a dangerous threat to the Patriots. Lewis recognized an opportunity to strike Dunmore’s force before it could escape.
Lewis ordered the batteries into action. The upper battery, armed with eighteen-pound guns, concentrated on the Dunmore, while the lower battery worked to silence the batteries closest to the mainland on Gwynn’s Island and drive away or sink the armed tenders afloat in Milford Haven. The Patriots were short on both powder and cannonballs and needed to make each shot count. The initial cannonade lasted about two hours. The Dunmore was struck five or six times in the hull before cutting its anchor cables and moving out of range. As Dunmore was moving away, a cannonball penetrated the stern of the ship. It passed through Dunmore’s cabin, splintering his leg and destroying his china. Another round killed the boatswain, and yet another removed a man’s arm. (Several days later, the Dunmore would lose its mainmast, indicating that the exposed upper rigging of the ship had been damaged as well.) The small crew could not afford any more losses. It returned a few ineffective rounds from the six-pound guns before moving out of range.
The Otter, ready to be heeled over for hull scraping, was the next target. The inexperienced but effective Patriot gunners managed to place one round into its hull, near the waterline, as its cables were cut to allow it to escape. Several tenders standing watch in Milford Haven were driven ashore on the island, set on fire, and abandoned by their crews. The lower battery silenced the guns on the mainland and knocked down the tents and encampment erected to support the soldiers. A break of several hours allowed the Patriots to cool the cannon and resupply ammunition before firing resumed. But the physical and psychological damage inflicted by a few hours of effective cannon fire was enough to convince both Dunmore and Hammond that the island was not defensible and that an infantry assault was coming.
The Patriots suffered only one reported casualty: Captain Louis d’O’hickey Arundel, a French volunteer serving as the battery commander of the Patriots’ artillery. Short on artillery and lacking mortars, Arundel built an experimental mortar crafted from a log banded with iron. He paid the ultimate price for his experiment. As warned by several senior officers, the mortar burst, and Arundel was partially decapitated. He had trained his men well in his short time in command, however. After his death, two officers assumed command: Lieutenant Charles Harrison in the upper battery and Lieutenant Samuel Denny in the lower battery.
The Patriots had more than enough infantry to overrun any defense the British could present. Dunmore and Hammond wisely evacuated their forces from the island. After just over a month of relative security, the British occupation of Gwynn’s Island ended as quickly as it began. Hammond, understanding that a large warship near the shore was an inviting target, kept the forty-four-gun Roebuck—the most capable warship in Dunmore’s flotilla and a critical component of an effective evacuation—well offshore and out of range.
The Patriots assembled about thirty canoes, enough to ferry about 200 men across Milford Haven to occupy Gwynn’s Island. At about 10 o’clock on the morning of July 10, Lieutenant Colonel Alexander McClanahan of the 7th Virginia led the crossing supported by Patriot cannon fire. This force included men recruited from neighboring King and Queen by Captain Gregory Smith. Two of the six-pound cannon were repositioned to support the crossing under the command of the acting battery commander Charles Harrison, who fired on a tender patrolling the channel. Smith’s men boarded the tender so that it could not escape. With the tender neutralized, McClanahan led the assault force onto the island.
What these men found “struck them with horror.” There were dead bodies everywhere, some in shallow graves, others exposed. There were also a number of dying men, barely hanging onto life, members of Dunmore’s Ethiopian Regiment, who were so sick they were unable to evacuate. Hundreds of both white and Black Loyalists, perhaps as many as 500, perished on Gwynn’s Island from disease. The island was also littered with supplies either damaged or abandoned during the withdrawal. The battle to retake Gwynn’s Island was over.
Aftermath
Dunmore’s fleet, reportedly consisting of ninety-six vessels, loitered at the mouth of the Piankatank River just north of Gwynn’s Island for a day, and on July 11, headed north. A strong wind the following day caused some smaller vessels to founder and beach themselves. The now smaller fleet anchored off St. George Island, Maryland, in the Potomac River on July 12. On July 15, a landing party of several hundred men sacked abandoned houses on the island and confiscated some livestock. The landing party returned on July 16 and was met by about 100 Maryland militia under the command of Captain Rezin Beall, who repulsed the landing—one of the larger skirmishes in Maryland during the revolution.
Dangerously short on water and with none available in the lower Chesapeake Bay, Hammond led a task force ninety miles up the Potomac River to Dumfries, where a landing party found fresh water. On July 23, the force landed south of Dumfries at Aquia Creek. After filling their water casks, they skirmished with the Stafford County Militia, burnt some buildings, and departed.
Dunmore’s flotilla was so short of water that crews attempted another landing on St. George Island on July 25. Again repulsed, they set fire to several buildings and fields. Hammond and Dunmore returned and provided fresh water to the flotilla. By August 5, the convoy had split. Thirty vessels under the Otter headed south to St. Augustine, East Florida; the Fowey escorted several ships bound for England into the Atlantic; and the remaining vessels, including the Roebuck and the Dunmore, headed to New York.
Although the British continued to send warships and privateers into the Chesapeake Bay to disrupt commerce and raid coastal areas, Virginia would not be occupied by the British again until Benedict Arnold, William Phillips, and Charles Cornwallis arrived in 1781.
