On May 23, Brig. Gen. Andrew Pickens decided on a plan to dislodge the Loyalist garrison at Fort Grierson and intercept the Loyalists before they could reach nearby Fort Cornwallis. Fort Grierson, was surrounded by Pickens and Lee and Maj. Eaton, and a battery was opened up against it. Maintaining the siege and keeping watch on Fort Cornwallis were the Legion cavalry under Major Eggleston, and some of the militia. Brown tried to make a sortie to thwart the effort, but was himself driven back into Fort Cornwallis where he cannonaded the besiegers instead. A while after, Lieut. Col. Grierson issued from the fort of his name, in an effort to escape to Fort Cornwallis. A sharp skirmish ensued, and upwards of 40 of Grierson’s men were captured, while Grierson with a handful of others, by moving under the cover of the river bank, were able to reach Fort Cornwallis in safety. In addition, the loyalists lost 30 killed. Pickens and Lee captured two cannon from Grierson, which they then proceeded to deploy against Fort Cornwallis. The Americans lost two wounded, and Major Pinkertham Eaton killed. Some accounts claim that in the shuffle of what transpired he was taken prisoner and his death occurred moments after the fighting had already ceased. Capt. Robert Smith subsequently replaced him in command of the North Carolina Continental detachment.

Simcoe ordered most of the infantry up to support his cavalry, and sent the jägers and light infantry into the woods on the right to flank the arriving enemy column. By questioning the prisoners, Simcoe learned that Lafayette was not far off. He sent word to Cornwallis, dispatched the cattle convoy toward Williamsburg, and ordered trees to be felled to make a barricade across the road as a point of defense. He then arrayed his troops in a way calculated to mislead the Americans into believing that more troops were in formation just over a rise. When Butler's force arrived, Simcoe ordered an infantry charge. This scattered the first wave of Butler's men into the nearby woods, where the jägers then pushed them back. However, Butler's men continued to advance. Simcoe ordered a cavalry charge and fired a field cannon to give the impression that a larger force was arriving. The charge forced Butler's men back, at which point the two forces disengaged, Simcoe because he was concerned that Lafayette was approaching, and Butler because his men were fooled by Simcoe's stratagem. Simcoe left his wounded men at the tavern under a truce flag, and withdrew down the Williamsburg road, joining with forces Cornwallis sent about two miles down the road. The Americans retreated to Lafayette's camp at Tyre's Plantation, and Simcoe was able to return to the tavern and recover his wounded.