After the Confederate collapse at Five Forks Lee found himself in a tight spot; he was facing a very different Army of the Potomac than the one he had first faced down during the Seven Days. Then he only had to strike and McClellan could be counted on to back up win, lose or draw; but now, Lee faced Grant and Grant worked with a very different calculus.
After Five Forks Sheridan had an unimpeded line to the South Side Railroad, Lee’s lifeline. Upon hearing of the Confederate collapse on his left Grant ordered a general assault on all fronts which resulted in breakthroughs everywhere. Lee seeing the inevitable had finally come to pass ordered a fighting retreat back toward Richmond to give the army and the government time to evacuate the city. Lee knew his exhausted soldiers couldn’t buy him much time, but under the circumstances anything would be helpful. In the general confusion Lee knew his various units would become separated and cut off so he gave the order for all units to regroup at Amelia Courthouse if they could not make it to Richmond.
In Richmond the Quartermaster began loading wagons with stores from his warehouses, at the same time the well to do begin to loading wagons with furniture and bric-a-brac from their own houses. Someone came up with the idea of attaching the wagons of furniture and whatever to the wagons full of army supplies. It may have been the wagon drivers themselves who, unsure of where they were going or how to get there, fell in line with the other wagons heading out of town. Perhapse they saw all of the wagons heading off togather and figured it was the only road out of town.
The government caught the last train west carrying with them wherever records they could scoup up at the last moment. With the leading citizens also hopping the train Lee and his army was left behind to do whatever he wished. As the soldiers fell back into Richmond the Quartermaster threw open the storehouses and began distributing supplies to the passing troops because he knew whatever was left behind would be burned. So the story of the ragged Southern Army retreating from Richmond is a myth. Most of Lee’s soldiers marched out of town wearing brand new uniforms and for the first time in the war carrying a full pack. They also carried three days rations.
The ragged soldiers of legand actually marched out of Petersburg. The supply houses were also opened up in Petersburg before they were burned, but the Confederate soldiers there did not have a lot of time once the the orders came to abandon their positions. Many of Petersburg's defenders fell back west away from town and never had a change to grab anything for the road, anyway. The Richmond soldiers on the other hand marched out of town right past the supply dump and were encouraged to take what ever they could carry.
Not that they carried much very far. Lee’s plan was to follow the South Side Railroad west to Amelia Court House, then turn south to join up with Johnston at Danville and form a guerilla force to carry on the war. I have never understood Lee’s thinking on this, the war was lost, it had been lost the moment the Army of Virginia had go into fixed positions around Petersburg: Lee had said as much himself after Grant crossed the James. What could he possibly hope to accomplish in the west with a guerilla campaign? The only thing that could have come from it was more death, more destruction, and the prolonged suffering of people who had suffered too much already.
Anyway, so it was that Lee's army left Richmond for Amelia Court House carrying full packs and three days rations while the Petersburg defenders hit the road with whatever they happened to have on them at the time the line collapsed. The decision to travel to Amelia Court House was not arbitrary, Lee's army was split between the defenses at Petersburg and Richmond, Amelia Court House was equal distance from both cities and could be reached by good roads from both locations.
Once Lee's army had reformed at Amelia Courthouse he was forced to pause a full day while teams of scroungers canvassed the countryside for food. The three days rations the men from Richmond carried really amounted to a little bacon and a few ears of corn, Lee's men were going to need a lot more than that if they were going to out run the Army of the Potomac and most of the Petersburg men didn't even have that.
Some supplies had made to Amilia by rail but not nearly enough and distribution proved to be problematic. Some units, the first on scene, were fed while those arriving later were not. The scroungers, going door to door begging for anything, found nothing for the army, the whole area was already picked over and itself hungery.
Something that has bothered me is why Lee didn’t detail men to go through the wagons and toss everything not militarily useful. Had they done so they would have cut the number of wagons in half or better; the remaining wagons could have been double teamed or at least hitched up with the strongest mules; and they would have found that many of the wagons contained flour, corn meal, bacon and smoked hams. I have read all kinds of arguments, should the wagons have split off from the main column at Holts Corner, should Lee have tried to break out at Appomattox, but I am convinced that nothing Lee could have done to effected the outcome of his retreat would have mattered more than an issue of corn meal biscuits and ham to his troops at Amelia Courthouse.
My own personal speculation is that Lee was exhausted and not thinking very clearly by this point. He might also have been suffering heart problems. None of his staff must have been thinking clearly either, if nothing else why didn’t they kick the wagon train loose to fend for itself. Grant was focused on Lee’s army and the wagons might have got away if they had just shuffled off to a quiet corner of the war and hunkered down. Another factor that must have had an effect was the wagon drivers themselves. At least half of them were slaves who had been told to take this wagon full of valuables out of town, probably to Danville. If I were in their position I would know that if the army gets any food they aren't going to give any to me, if somebody asks what I'm carrying, I'm not going to say anything about a barrel of flour and a smoked ham hidden under the piano; I'm going to save that for myself. In fact, if the opportunity presents itself, I would abscond with the wagon and head north. Of course, because of the Appomattox River the chance would not come up before Farmville and very few of the wagons made it past Saylor's Creek.
The upshot was that Lee didn't check the wagons, he thought only about escape with his army intact. To do so Lee needed to move fast and far but he couldn't move anywhere quickly dragging a wagon train full of pianos.