They were called Kaintucks whether or not they came from Kentucky: farmers and boatmen off the Ohio and the upper Mississippi who built a flatboat, loaded it with corn, pork, whisky, hemp or tobacco, floated it down to Natchez or New Orleans, sold the cargo, then sold the boat itself for its planking, and turned round and walked. More than ten thousand of them came up the Natchez Trace in 1810 alone, which made it for a few years the most travelled road in the Old Southwest, the country that became Tennessee, Alabama and Mississippi. They built the boat, and selling it was always part of the plan; the timber was worth more at Natchez than the trip back was worth in shoe leather. Corn, pork, whisky, hemp and tobacco all went down that way and none of it came back.
The walk was five hundred miles and took about thirty-five days on foot, twenty to twenty-five for anyone with a horse. They landed at Natchez-under-the-Hill, the wharf district below the bluff, whose reputation for gambling, drink and violence was very largely their doing. A man carried his money on him, which is exactly what made the road worth robbing. And they came back: the ten thousand is an annual figure, and many of them were professional river men who made the round trip year after year until a steamboat would take them upstream for a few dollars and none of them had to walk it again. By 1830 almost nobody was making the walk at all.
Getting there
35.3209, -87.5805
Locations are approximate and may be inaccurate, on private land, or otherwise inaccessible. Check before you travel.