Sheridan had ridden into the box on purpose, though not this particular box. The raid was meant to draw Stuart out, and at Yellow Tavern it had worked. But the storm and the darkness had pushed the column farther south than Sheridan intended, into the corridor between Richmond's intermediate fortifications and the Chickahominy River. Fitzhugh Lee's artillery now had range on the road. Citizens of Richmond were being pressed into uniform and sent against the rear. On the western end of the Union line, near Brook Church, David Gregg's division held off James B. Gordon's Confederate brigade. On the eastern end, James H. Wilson's troopers absorbed pressure from Mechanicsville Pike. Sheridan needed a crossing, and the only one within reach was Meadow Bridge, where the Virginia Central Railroad spanned the Chickahominy - except the Confederates had stripped the road decking off the night before.

The job went to George Armstrong Custer, leading the Michigan Brigade under Wesley Merritt's division. Custer's 5th Michigan Cavalry positioned snipers to suppress Confederate rifle fire across the river while dismounted troopers stepped out onto the open ribs of the railroad bridge. They hopped tie to tie above the swollen Chickahominy, exposed the whole way, while Confederate artillery searched for the range. The 6th Michigan followed. By early afternoon they had cleared the north bank and seized a foothold on the Confederate side, capturing two artillery pieces. Behind them, Union pioneers were already planking the bridge for horses. By mid-afternoon Merritt's entire division had crossed and pushed the defenders back to Gaines's Mill. By four o'clock, the rest of Sheridan's cavalry was over.

While Custer worked the bridge, the rest of the trap was trying to close. Gregg's rearguard was hit from three sides as Confederate infantry sallied from the fortifications, joined by hastily mustered Richmond citizens. The 1st Pennsylvania Cavalry's regimental historian remembered the chaos. Wilson's men gave ground at first, but Gregg had concealed skirmishers armed with repeating carbines in a brushy ravine; their fire halted the Confederate advance cold. Federal horse artillery finished the job, and three mounted regiments turned aside the approaching enemy cavalry. James B. Gordon, the Confederate brigadier leading the attack, was mortally wounded in the fighting and died six days later. Sheridan reported 170 casualties across all the Richmond-area engagements that day - a remarkably light bill for an army that had spent the morning surrounded.

Once across, Sheridan destroyed the Virginia Central Bridge behind him and called a halt. His men collected their wounded, buried their dead, grazed their horses in the pastures along the north bank, and did something that says more about the strange intimacy of this war than any battle report: they bought Richmond newspapers. Two enterprising small boys had slipped across the lines with armfuls of city papers and were selling them to Union soldiers, who wanted to read what the Confederate capital was saying about the cavalry raid that had killed their most famous cavalier and just escaped their best trap. The riders pored over the columns about themselves while their horses cropped grass. Then they remounted and rode on, the raid continuing south toward the Army of the Potomac.