The Spanish built Silver Street
about 1790 to connect the town to the riverfront below. In the 1800s, Natchez Under-the-Hill was a major port on the Mississippi River. Natchez exported and imported agricultural goods, with cotton being the primary export. As the city became richer, the imported goods grew more luxurious.
A newspaper article about a devastating 1840 tornado at Natchez estimated that 100 flatboatmen had perished and noted that the "immense quantity of pork, bacon, lard, and vegetables lost at the Landing—swept into the deep and oblivious river—would astonish anyone not acquainted with the nature of our trade."
Shipments in and out of Natchez also included large numbers of enslaved people. The region's expanding cotton economy and the growth of steamboat traffic on the Mississippi River increased the number of enslaved people shipped to Natchez. The river also offered a route to freedom. Escaping slaves hid on steamboats or carried counterfeit freedom papers and made their way to freedom.
Saloons, hotels, warehouses, grocery stores, a coal yard, an ice house, a quarter-mile race track, a ten-pin alley (bowling), and even a few private residences lined the streets of Under-the-Hill. Many of the businesses existed primarily to service the flatboats, keelboats,
and steamboats that docked at Natchez.
Natchez was a city with a dual personality. One writer described the conflicting characters of the city on top of the hill and the city Under-the-Hill as "Natchez proper" and "Natchez improper." Natchez improper had gambling dens, saloons, and houses of prostitution that were popular with the rough boatmen and travelers at the waterfront.
In 1816, an account written by traveller William Richardson was published that described Under-the-Hill as
"...without a single exception the most licentious spot that I ever saw. It is inhabited by the worst characters and it is well known that not a virtuous female will ride in this polluted spot. From this filthy spot emanate all the contagious disorders that infest the town above."
A Captain J. E. Alexander described Under the Hill in a colorful account published in 1833:
"The lower town of Natchez has got a worse character than any place on the river; every house seemed to be a grog shop, and I saw ill-favoured men and women looking from the windows. Here the most desperate characters congregate, particularly in the spring of the year, when the upcountry boatmen are returning home with their dollar-bags from the New Orleans market. Dreadful riots occur... eyes are gouged out, noses and ears are bitten and torn off..."