General Alexander Leslie's 1780 raid focused on Hampton Roads because British warships could not go far upstream in the shallow channel of the James River
Source: New Yor Public Library, A New and accurate map of Virginia: and part of Maryland and Pennsylvania (1780)
Loyalists in Virginia and enslaved people seeking to escape to British lines were pleased when Major General Alexander Leslie sailed into the Chesapeake Bay with 2,200 men on October 20, 1780.
The last British forces in the state had both arrived and departed in May 1779. That raid, led by Commodore George Collier and Major General Edward Mathew, destroyed supplies at Suffolk and the Gosport Shipyard at Portsmouth but left after two weeks. Without a permanent British base in Virginia, the rebels dominated the region and suppressed their loyalist opponents.
The purpose of Leslie's raid was similar to that of the Collier-Mathew Raid. Virginia was a source of men and supplies to the Continental Army fighting in New York and in the Carolinas. Around New York City, George Washington and General Henry Clinton were in a stalemate. After the French entered the war, British officials redirected ships and troops. Clinton was not sent enough men to attack and defeat Washington.
Instead, the British adopted a "southern strategy" and hoped to recapture the colonies south of Virginia. Savannah was seized in 1778; Charles Town fell to an invasion force led by General Clinton in 1780. He left General Charles Cornwallis to establish loyalist control in South Carolina, but the rebelling colonists there kept receiving replacement soldiers and supplies from Virginia.
Whenever British soldiers left an area, rebellious South Carolinians regained control over the countryside. Like General Clinton, Lord Cornwallis also lacked the resources to implement the southern strategy to expand royal control beyond Charles Town and scattered outposts.
The British were unable to establish an army large enough to occupy the rural areas in the South Carolina and Georgia "upcountry" in order to maintain British control; too many troops were needed in the Caribbean to defend the sugar islands against the French. The British anticipated that if they defeated the organized military forces in the southern colonies, then the southern loyalists would be emboldened. Once enough loyalists enlisted and were willing to fight, rather than just take an oath of loyalty and sit on the sidelines while the British Regulars fought, then royal government could become effective again in the backcountry outside of Savannah and Charles Town.
British military victories at Charles Town and Waxhaws in May 1780 and at Camden in August 1780 suggested the southern strategy was succeeding. Completing the task of defeating the Continental Army forces and partisans in the southern colonies would require interrupting the delivery of new troops and supplies from the north through Virginia.
General Leslie was ordered to sail up the James River and capture Petersburg and Richmond, destroying the central supply depots and diverting reinforcements headed to General Nathaniel Green in North Carolina. After landing at Portsmouth, Leslie discovered that the loyalist support in Virginia was weaker than expected while the Virginia militia was stronger than expected.
He also realized that sailing up the James River required a local pilot, and could not get one. Leslie decided to ignore the plans developed in New York City and to use the mobility provided by his warships to raid just coastal areas.
Governor Thomas Jefferson still feared a raid deep into the interior of Virginia to free 800 British soldiers who had been captured at the Battle of Saratoga in 1777. They were imprisoned in the Albemarle Barracks near Charlottesville, so Jefferson shipped them further away from the coastline to Maryland. He left the Hessian prisoners in their Albemarle Barracks, assuming General Leslie would not risk a long-distance raid to free the hired Germans.1
Governor Jefferson also moved supplies inland, though Leslie was able to seize and destroy significant amounts of material at Suffolk, Newport News, and Hampton. He was constrained in his ability to send militia from the Piedmont counties to Portsmouth because loyalists were threatening to rebel against the rebelling Virginians. He wrote to the Virgina delegates in the Continental Congress:2
General Henry Clinton could have chosen to reinforce Leslie and enable him to move inland, but their plans were shaped by the march of the Overmountain Men to Kings Mountain. After they defeated Major Patrick Ferguson and his loyalists, Clinton directed Leslie to leave Virginia and go to Charlestown, South Carolina.
The Virginians who succeeded in forcing General Leslie to abandon his raid after less than a month (October 30-November 22, 1780) were not the Tidewater militia. Instead, it was Colonel William Campbell and his volunteers from southwestern Virginia, united with Tennessee patriots, who won a battle at Kings Mountain on October 7, 1780. The defeat of Ferguson, and the loyalists he commanded, was the trigger for the British to alter their plans in Virginia.
After the defeat at King's Mountain, General Charles Cornwallis decided not to go into winter camp. He chose instead to march into North Carolina. After spending only a month in Hampton Roads conducting raids, Leslie left for Charles Town on November 18, 1780 to reinforce Cornwallis.
Thomas Jefferson had anticipated Leslie's withdrawal when he wrote to George Washington on November 3, 1780:3
Leslie's troops arrived in South Carolina too late to participate in the battle at Cowpens on January 16, 1781. They did join in the "race to the Dan" afterwards, as Cornwallis sought to engage General Nathanael Greene's Continental Army fleeing north. Leslie was in command of the right wing when the British won a Pyrrhic victory over Greene's army at Guilford Courthouse on March 15, 1781.4
General Clinton in New York quickly arranged for another invasion of Virginia. He sent General Benedict Arnold south from New York in December, 1780. There was a British army marching through Virginia for the next 10 months commanded first by Arnold, then by General William Phillips, and finally by General Cornwallis.