From the 1st to 3 January, Arnold's fleet sailed up the James River, laying waste to plantations and settlements along the way. On 4 January, the British reached Westover Plantation, where they would ready themselves for the assault against Richmond. In the afternoon, Arnold and his men disembarked on foot towards Richmond.

The following day, Arnold's force of Loyalist "green-coats", consisting of infantry, dragoons, and artillery, arrived at Richmond, which was defended by approximately 200 militiamen. Surprisingly enough, most Virginia militiamen had not bothered to defend their capital because they had already served their time in battle, and thought that their duty was up. Upon seeing the group of Virginia militiamen, Colonel John Graves Simcoe, of the Queen's Rangers, ordered a detachment of soldiers to confront them. The militiamen fired a weak musket volley at the advancing British, and then broke and ran into the woods, with the Loyalist detachment chasing after them. Jefferson, seeing his militiamen dispersed, and no other plausible way to defend Richmond, quickly ordered the mass evacuation of most military supplies from the city, and promptly fled in his carriage, along with the rest of Virginia's government officials and his family.

At noon, Arnold's forces marched triumphantly into the city, described by an eyewitness as "undisturbed by even a single shot." From his headquarters at Main Street's City Tavern (he would only stay in Richmond for a day), Arnold wrote a letter to Jefferson, offering to spare the capital if he was allowed to seize tobacco unmolested. Jefferson refused the terms, and the city suffered the consequences.