During the mid 1700's, men known as the Long Hunters" explored and hunted in the Middle Tennessee region. They were usually gone from their home for more than a year at a time, to hunt and collect pelts and other animal products, then they would go to Natchez to sell their goods. It is known that the Long Hunters used the Mississippi River system to get their products to Natchez, but it is undocumented how they got back to their homes in the Tennessee country. But it is widely assumed that the Long Hunters marched back overland along the Trace. If this is true, they would have been the first Americans to use the Natchez Trace as a road for business.
The earliest documented American travelers of the trace were the people of the Kentucky and Tennessee river valleys known as "Kaintucks" or flatboatmen. At this time, the only market place for the mountain settlers of Tennessee and Kentucky to sell their goods was Natchez, the oldest city on the Mississippi River.. To get to market, the farmer or mountainman had to build a flatboat, load it with his produce and pelts, and float it down the Ohio, Cumberland and Mississippi rivers. Once there, and the goods sold, the Kaintucks would break up their flatboat, sell it for lumber or even abandon it if necessary, since it was impractical to try returning by the river against its flow. If the farmer or mountainmen had made a good sale, they might buy a horse for their return trip. If the sale was bad, they would return on foot. In any case, in those early years, the return route home used most often was the old Natchez Road as the Trace was known at this time.
The 450 mile journey from Natchez to Nashville took fifteen to twenty day. It was these return trips that later made the Natchez Trace famous (or rather infamous would better describe it). Robbers, and outlaws, known as highwaymen, were common on the Natchez Trace. Since the Mississippi Territory was where travelers with money were, the highwaymen ended up there also. The Trace attracted large numbers of the lawless who survived by stealing and killing boatmen and other travelers. There are many stories of murders along the Natchez Trace. Tales of travelers being robbed, killed, then disemboweled, their body cavities filled with stones, and then the bodies submerged in some nameless creek were heard throughout the area.
Natchez was an important military and economic site in the early 1800's, so communication between Natchez and Washington, D.C., was needed, and necessary for all. In 1800 Congress extended mail service to Natchez. The Postmaster General complained that it was a bad road, no more than an Indian footpath, and too treacherous to use. In 1801, President Thomas Jefferson ordered the army to clear the road for the new postal route. Army troops cleared underbrush and built bridges. In 1806, Congress gave the Postmaster General $6000 to contract outside the army for improvements, and within a short time the old Indian trail became an important frontier road. Inns, or "stands", as they were called, began popping up every few miles along the Trace. Stands were operated by both Indians and whites, and offered food and lodging to the weary traveler By 1818, there were 50 stands and trading posts along the Trace from Natchez to Bear Creek on the Alabama border.
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